The Legend of Listener's 1,000-Mile Booty Call
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Category:
Original - Misc › Non-Fiction/True Stories/Autobiographical
Rating:
Adult ++
Chapters:
1
Views:
1,532
Reviews:
2
Recommended:
0
Currently Reading:
0
Disclaimer:
This is a work of non fiction. Where possible - and where appropriate - permission has been granted from any people or their descendants to be included in this story. The Author holds exclusive rights to this work. Unauthorized duplication is prohibited.
The Legend of Listener's 1,000-Mile Booty Call
The Legend of Listener's 1000-Mile Booty Call:
The True Story That Made Me A Legend
(at least, among my fraternity brothers)
*****
Warning: this is creative nonfiction. That means I'm looking back on it while being older and wiser, and I can't remember every detail exactly. To the best of my knowledge, this is as close to the truth as I can remember, except for changing 90% of the names.
This story contains sexual practices that may be considered unsafe. Always use protection.
*****
At 18, I wasn't what you'd call outgoing. I was in a new place, just starting college, and all my attempts to be the cool guy failed. Miserably. I was still just another geek -- a geek with other geeky friends, and some not-so-geeky friends who, like me, were in the Honors program -- but I wasn't the cool guy I wanted to be.
I think, in retrospect, that hanging upside-down over the back of a couch while at a mixer for my dorm might not have been the best option.
I actually have some pretty good memories of my freshman year at college. Aside from my ex, Crazy Mary, breaking up with me over the phone and eventually writing a chapbook about the guy she left me for, it wasn't bad at all. I met a lot of great people who are even now sitting on my Facebook and MySpace pages, waiting for me to go send them messages. And in my second semester, I met my wife -- of course, at the time, she wasn't my wife, but that's neither here nor there.
I also met Diana.
When I was in high school, I spent a lot of time online, mostly on ChatLink-affiliated BBSes or the BBSes I cosysop'd. Even when I was dating Crazy Mary -- she who took my virginity in the backseat of my car as it sat in my driveway, hidden by a car cover -- I still spent hours talking to all sorts of people, most of whose real names I never knew. In college, though, I didn't know about any BBSes.
My mom had AOL. I had her password.
You can guess what happened next.
Hey, I was eighteen. Not my fault I downloaded lots of porn.
Even at eighteen, I was already a kinky person -- or, at least, I thought I was. Mary and I had had anal sex a few times, and though she didn't care for it and I never actually came in her ass, I had enjoyed the few moments of exceptional tightness that act provided. I've since done it with two other women, and neither held me as strongly as Mary did.
As for BDSM? Mary allowed me forays into that as well. I spanked her on several occasions, a couple of times to the point where her ass actually was almost red. She never really complained, I think because she was afraid I'd leave her if she said no.
I wouldn't have.
I also put a collar and leash on her once or twice, for shock value, leading her around by it (she was walking, not crawling) while we hung out with our friends. I verbally dominated her from time to time, ordering her to remove various items of clothing, walk to my house without underwear, wear certain outfits I thought looked good on her, and once or twice having her show her breasts while we drove. Always at night, but there was still the thrill of danger, of someone seeing.
I was drawn to kink even then. When my friend Amy said her boyfriend spanked her -- it came up in conversation legitimately, don't ask me how -- I asked her, "in what way?" She stuck out her hip and slapped it.
That night, I wrote a fairly-crappy short-story about how I really wanted to handle that moment -- to invite Amy back to my house and give her a real spanking. I never did, and now Amy and I are very good friends who never discussed that moment again. She's on my MySpace page too.
So with all this kink floating around, it's no surprise that I spent a lot of time on AOL's newsgroup reader, chatting on the A.S.S. board (before it became S.S.S.), and also in AOL's D/s chatrooms. I tried not to be That Guy, the one who instantly IM'd anyone with "female" in their profile. Instead, I talked to people. Guys and girls.
Which is how I met Diana.
I don't know what Diana was expecting when she talked to me those first few weeks. All I know is that she was twenty-nine -- eleven years older -- and that we had some common interests. She liked sci-fi, BDSM, and good books, just like me. I suppose our ages came up at some point -- I didn't have mine in my profile because I wanted to be judged on who I was, not how old I was -- but once Diana learned I was a legal adult, I guess nothing else mattered.
Or maybe she knew I would just end up being a one-night stand.
In October, Diana mentioned that she'd be making a trip along the eastern seaboard to visit friends, and wanted to know if I wanted her to stop in Orlando. At that point, I had no idea of what might happen, but I had hopes. I hadn't had sex since Rosh Hashanah, my whirlwind 36-hour trip back home -- Mary, only five days before breaking up with me, had let me fuck her in my backseat as the car nestled hidden in a loading dock behind what is now a Home Depot. It had been good sex, though somewhat unfulfilling; we both came, but I'd had to pull out before I did and when she jacked me off, I spurted so hard that it hit the side of my mouth.
Like I said, it had been a while, especially since, before I moved away, Mary and I had been having sex at least twice a week.
But Mary broke up with me and I didn't have any prospects on the horizon. No real ones, anyway. Marianne was on the crew team and didn't have time; Gina was way out of my league and had a long-distance boyfriend in any case; Hope was hopelessly devoted to my roommate in the hopes that he would ask her out; and Bella was the object of my suitemate's affections, thereby putting her in "don't ask her out if you don't want to piss off your friend" territory. There were other girls in my network, so to speak, but none I really thought I had a chance with.
The idea of possibly sleeping with Diana had its perks. Sleeping with… and more… especially since she was twenty-nine and would be getting a hotel room.
I have since had sex in a dorm room. It was very difficult to keep quiet, but it helped that my roommate slept like the dead.
But I digress.
In 1996, there was no cheap and easy digital photography. Photos had to be scanned, a time-consuming process made more so by the lack of good plug-and-play. Neither Diana nor I had seen photos of each other; I would know who she was by the color of her car, by her license plate numbers, by the fact that she was five-foot-six and blond, by her glasses in conjunction with all of that.
In return, I told her my height, that I was kind of a big guy, that I would be wearing a certain pair of jeans and a certain shirt.
We had plans to go see Star Trek: First Contact; it wasn't like I needed to dress up. As much as I wanted Diana to take me to bed, I had no expectations.
I gave Diana directions to the parking lot outside my dorm -- now itself another dorm building; parking at my college was always bad, but when I finally left after getting my Master's in 2002, it was nigh-impossible -- and waited for her call. She was coming down I-95, and when she got to a certain exit, she would call me -- this was before cell-phones too, technically, and neither of us owned one -- so I would know where she was.
She called at 4:00.
I was showered, shaved -- obsessively trimming my goatee until it got so messed up that I finally just sheared the damn thing off -- and dressed at least forty-five minutes before she was to show up.
And I couldn't do anything else. I tried to read, tried to study, tried to work on a paper, but nothing worked. I ended up relaxing on my bed, watching a show I'd taped, only half paying attention.
It did help. The clock moved, and 5:15 eventually came.
I went downstairs, heart hammering, not even entertaining the thought that Diana might be an AOL-meeting-from-hell-in-the-making. Such things hadn't even hit the news yet. There was no way Diana wouldn't at least be passably pretty -- at that age, that was still more important to me than who she was, and I'm really quite embarrassed to admit it.
Fortunately, her appearance was not a problem. Not at first, and certainly not later.
"Hi."
I held out my hand. "Hello." My voice didn't crack, thankfully. "It's nice to meet you."
"Nice to meet you too." She pointed at the car. "Should we go? The movie's in twenty minutes."
I nodded and got in; she went around to the driver's side and, after buckling up, I started giving her directions to the theater.
I did manage to avoid staring, but then, Diana was… well, there's no nice way to say it. She was plain. Not unattractive by any means -- to this day I still have a few photos of her laying around -- but nothing terribly special. The eighteen-year-old me took note of the fact that she had fairly-large breasts, try as she might to hide them under a t-shirt and a flannel. She wasn't fat, but wasn't thin; her face was a rounded oval -- the tall kind, not the wide kind -- and her hair, while blond, could have probably used a little work. Her hair fell halfway between her chin and her shoulders -- shorter than long, but longer than short. If I'd met her today, I'd have said her jeans were flattering, but that's with the benefit of having since seen her naked. They made her ass and her legs look good.
But one thing about Diana made her, for the moment, the most attractive woman in the state of Florida:
She was interested in hanging out with me.
We both enjoyed the film -- First Contact is arguably one of the top three Star Trek movies, possibly even one of the top two, although I prefer II and VI to VII any day. Afterward, though, Diana said she wasn't feeling so well and wanted to lie down. We went back to the hotel and I told her I would walk over to the plaza and pick up dinner.
It was McDonald's, but then, I had asked her what she wanted, and I was too naïve to know that when a woman says that, it's not really what she wants to eat. The food helped her feel a little better, though, and by 9:00 we were staring awkwardly at each other, her on her stomach on the bed, feet by the pillows, and me on my knees, face close to hers.
I don't remember who kissed whom. It was a nice kiss, not terribly memorable as kisses go but not bad at the time. It made me acutely aware of the fact that I had two condoms tucked in the back of my wallet, two of a supply that hadn't been replenished since before I came to college. Had they reached their best-by date, I don't know what I would've done -- probably not even brought them, and missed out on this -- but they still had eight months left, so I felt safe enough.
We kissed for a while, moving up onto the bed, hands wandering across each other's bodies. I discovered that it was indeed possible to have breasts that large that were also firm -- though I didn't see them at the right angle until later, I could tell they had that perfect shape that breast connoisseurs and horny teenage boys covet. She was -- still is, I'm sure -- at least a D-cup, possibly a DD, but there was barely any sag.
I didn't pay enough attention to them. Or to her neck, or her arms, or any other part I would normally lavish attention upon. I was too busy working my way down, working her out of her jeans and me out of mine. I must recall with some dismay that, at the time, I had not yet discovered the joys of boxer shorts, so you can imagine what the state of my underwear was.
Could've been worse; I don't even remember hers. I just remember kneeling at the foot of the bed, hiding my body, hiding the fact that I was overweight and that, without my shirt on, I was incapable of feeling attractive to anyone. Her sex was right in front of me, covered by her panties -- I think they were pink -- and I knew with every part of me that I was going to get to fuck this girl.
No. That wasn't right.
I was going to have sex with, possibly even make love to, a woman.
To this point, all of my sexual experience had been concentrated within the eleven months I dated Mary, and one fumbling evening with a nice but as-overweight-as-me girl I met when I was sixteen. Everyone before Diana… they were girls.
I couldn't possibly call Diana a girl. It would've been a slight that, had I done so, I might never have recovered from making.
Luckily, there was something else on my mind.
"Is there anything…" I swallowed hard, willing myself not to blush. "Anything I should… um… know?"
The ultimate question in the age of casual sex: do you have any sexually-transmitted diseases? Only this was my first time having casual sex. I had no idea how to ask the question. When I met my wife, she told me flat out that she was a virgin and had had very little sexual contact, but I had a level of comfort with her that I didn't have with Diana. I was intimidated by her, and more than a little; she would be my first casual sex experience, my first real one-night stand -- the girl when I was sixteen didn't count; we got naked, and then I made up an excuse to end the encounter -- and I didn't want to fuck it up.
Diana knew what I was asking. She gave me an answer that unquestionably equated to "no" without making me feel bad for asking.
That was when I took off her panties and began to touch her.
Ann, my first serious girlfriend, had been quite prudish, only allowing me to suck her breasts with my eyes closed, and I had obeyed her wishes. Our courtship had been rather sweet -- four mis-timed kisses at a youth center in Miami, more kisses the next day, sleeping in the poolhouse while she stayed in her bedroom, and on several occasions, my hands finding their way into her shirt.
And below.
I don't think I took advantage of Ann -- she was a few months older than me, though I definitely had more experience -- but I know for a fact she didn't know how to react when she permitted me to put my hand down the front of her clothes and touch her. She enjoyed it, but she never came. And I never saw what I was touching. No, Ann was too much of a prude to actually take off her shorts -- or, on one amazing weekend, to let me lift her nightgown enough to see her sex.
The overweight girl was shortly after Ann and I broke up -- it had been her idea, citing the hour-long drive between her house and mine and the fact that neither of us had a car or a license -- and my hands never went below her waist before I lost my nerve.
Mary had taken charge that first night, and as we sat in my backseat and kissed, as I fondled her breasts -- so much bigger than Ann's, so much softer -- and played with her neck and let my hand creep up her thigh to push her panties out of the way and find her clit… I'm sure that sentence was going somewhere, but the memory is too intense. Mary may have come; I didn't know her well enough to know if she did or didn't. I do remember, though, that she had quite a bit more hair down there than Ann had -- at least, according to what my hand was telling me -- but then Mary was more developed than Ann and for all I knew at the time, hair in that area was directly related to breast size.
Having never been both naked and intimate with a woman whose breasts were smaller than a C-cup, I still don't actually know the answer.
I had plenty of opportunity to get to know Mary's breasts, sex, ass, legs, stomach, shoulders, and all more mundane parts as well. And while I did love her, I didn't really love that she had apparently never gone farther than soap and water when grooming between her legs. Giving her head meant getting hair caught in my teeth. I did the best I could, but while I think completely shaving is a little disturbing, that much hair comes with its own problems.
Even though it hadn't happened when I knew Diana, I have to mention Tara, who I slept with several times toward the end of 1996 and in the summer of 1997. To this day, Tara is the only partner I've ever had who's completely shaved, and while it was an odd experience, what I disliked about wasn't the way it looked.
It was the way she smelled. Or, more precisely, the way her lotion smelled. To cover what she must have thought was an unpleasant scent, Tara used a strawberry-melon-scented lotion, and that was all I tasted as I knelt at the foot of her bed and brought my mouth to her clit. Had Tara not been so very responsive and so very into getting eaten, I might have given up.
Even giving up after a few minutes would've been more than I did for Diana. No, I was still so blown away by the very idea of seeing Diana naked, of sleeping with her, that I only used my hands on her until, by some unknown signal, she indicated that I should be on top of her, be inside her.
Condom? Check. And I even got it on in the right direction, which is a real pain when doing it by touch.
Our bodies joined easily. She arched to take my cock inside her, her sex warm and wet, so wet that I felt the slickness through the condom. Or so it seemed.
I can't complain about the sex, not really. It was good. Not as good as my first time -- Mary took my virginity, and I was so overwhelmed that I held back my orgasm for a good ten minutes, enjoying every second and every sound and every sensation -- but still good.
Too good.
Diana was a woman. I'd only been with girls before.
Diana was responsive. My cock had never elicited this kind of response from Mary.
Diana was going to come, and soon. But not as soon as I was.
I'd found a rhythm she enjoyed, one that made her moan and clutch at my shoulders. Unfortunately, it was also a rhythm that brought me so close to coming that I couldn't hold on, and though I didn't do anything stupid like hold up her legs and hammer into her, I know that toward the end I was moving quite fast in and out of the hot, clinging flesh of her sex.
It took everything I had to keep going afterward, even as my greatest fear leached away my erection -- that I had failed to satisfy this beautiful woman who seemed to want nothing more than to watch Star Trek and fuck me.
Diana had been close enough when I came that, only a couple of seconds after my last feeble twitch, she flew over the edge and joined me.
As I reflected on that moment in later years, I became more and more convinced that, while she'd most definitely enjoyed the sex, that hadn't been a real orgasm.
I have two reasons to say that.
First, we had sex twice more after that. She wouldn't have wanted me to be with her again if I'd been a complete fuck-up.
Second… well… that takes a little more explanation.
I had made Mary come on several occasions. Most of the time, in fact. I made it a point of pride, especially after reading so many online accounts -- most of them fiction, I'm sure -- of how women had been left unsatisfied by their men. I didn't want Mary to leave me for that reason.
I was dorky, I was fat, and I didn't have a lot of friends. Didn't do much for my self-esteem. College helped -- Diana helped -- but my senior year in high school was fraught with insecurity and the last thing I needed was to be dumped because I was no good in bed.
So I learned what Mary liked. I learned how she liked to be touched, how she liked to be kissed, how I should use my hands and how that differed from the way I used my mouth or my cock. Mary came. A lot. Not the copious-orgasm type of a lot; I mean in terms of frequency.
Mary was one of those girls who has one big orgasm and then is done for the night -- or at least for an hour or two -- and is fully able to concentrate on pleasing her partner. My wife is like that too, except she tends to be so languorous after coming that -- and I would say this is the case about seventy percent of the time -- by the time she gets her strength back we've been fucking long enough that I'm out of stamina.
Diana may have been one of those women. It may just have been the fact that she would be leaving in a few hours that changed the way we had sex the second time. I can't answer the question -- and I don't remember her last name, unfortunately, so I can't even look her up on the 'net.
But I'm glad to say that the second verse was nowhere near the same as the first.
I'd been woefully unprepared to spend the night in Diana's hotel room. I had my condoms, but no change of clothes, no toothbrush, no deodorant, no comb.
Diana didn't seem to care. I think it was me who woke her up as I came back from the bathroom. We kissed and snuggled together, naked under the covers, sharing warmth and the closeness that comes with waking up next to someone and realizing you're not regretful at all about the previous night.
For a moment, I actually entertained the thought of being in a relationship with Diana, of having her next to me every night. It was a pleasant thought -- her body was soft and smooth, her breasts were nothing short of spectacular, she felt good in my arms and fit well against me, and she'd seen me naked and wasn't completely repulsed.
The fact that we started to touch a little more insistently was proof of that. I found the second condom -- again with very little foreplay, either me to her or her to me -- and got it in place on my cock.
I was on my back.
And in a few seconds, she was straddling me, riding me, hot and tight, head thrown back, breasts so firm they seemed to barely move. I was mesmerized by them. I touched them, caressed them, pinched her nipples gently -- knowing somehow that treating them like radio knobs would be a bad thing -- but she didn't lean down far enough for me to kiss them. Or her.
But here was a beautiful woman riding my cock, bouncing up and down, making noises that said she was beyond happy.
It was heaven.
There was no way I would let myself come before Diana, not this time. I would not let her go back to Illinois thinking I was a selfish lover.
As she slid up and down on my cock, I worked my hand between our bodies and found her clit.
If I'd had any doubt before that I was pleasing her, this removed it completely. I felt the first stirrings of orgasm, that little tightening deep in my lower stomach, but when she came, I completely forgot about it.
Because when Diana came, she came.
My hands on her hips.
My cock gripped tight inside her body.
Her nipples small and hard on those glorious breasts.
Her head thrown back, then thrown forward.
Her thighs going stiff.
Her mouth opening.
And a noise that, to this day, I can't begin to describe, mostly because I don't remember it.
I was too lost in the feeling of her orgasm cascading down around the base of my cock, around my balls, a puddle spreading under my ass.
And too lost in the wonder of it to realize that she was riding me again, harder, faster, our bodies slapping together, my hips rocking up to meet her and falling back to squelch in the wetness soaking the sheets until I dug my fingers into the bedding and groaned her name and came and came and came…
Diana took a shower while I recovered, and by the time she got out, I was already dressed. That gave me the luxury to watch her put her clothes on, and it also let me observe her perfect breasts in their natural habitat, so to speak; that is, as she walked around, doing all the small things people do to get dressed after a really good fuck.
They really were absolutely flawless. I have never seen more perfect breasts before or since, except maybe after the application of Photoshop.
Once dressed, she drove me back to the dorm -- only a five-minute trip, as the hotel was right across the street from the college -- and after taking a few pictures, we said our goodbyes. Hugs, chaste kisses, and promises to e-mail and call, and then she was in her car and out of my life.
Back in my room, I changed my clothes, washed up, brushed my teeth, had a little something to eat, and tried very, very hard not to think about whether or not Diana had done this before, and whether or not she would do it again. She did say she was going up and down the eastern seaboard, from Virginia to Florida and back again. For all I know, she had fucked all her friends in all those other states, and was even now on her way to fuck someone in Miami or Tampa or Key West.
That afternoon and evening, we helped my roommate's friend Alfred move to a new apartment. It took my mind off things. The next day I sent Diana an e-mail -- though it was over AOL, so maybe it didn't really count -- and about a week later, I got a response: she was back home, everything was fine, it was great to see me, hoped to see me again, that sort of thing.
It made me feel good.
But not as good as what happened next.
This story would not be complete if I didn't mention what happened over winter break. In short, I arranged a meeting with Tara -- she of the shaved pussy, though it wasn't shaved when I met her -- after we chatted on AOL. She got my attention by sending me an IM and asking if I was into anal sex.
Even if I hadn't been, what eighteen-year-old in his right mind would say no, especially to a twenty-three-year-old woman asking him that question out of the blue? Again, this was before the days of internet dating horror stories, so when she told me what she looked like, I believed her.
I went into the meeting with no expectations -- we were to meet at a bookstore, a safe place, at the self-help section. She told me she was five-eight and about 180 pounds, and that she had blond hair and blue eyes. I sound shallow when I admit this, but I was a little disappointed when I met Tara -- she was at least forty pounds north of her stated weight. I wasn't disappointed at her appearance, though; I was disappointed that she lied.
Tara has appeared in various forms in various stories I've written, so I won't go into a lot of detail, except to say this: on New Year's Eve, my parents were out partying (probably at a friend's house, getting high or drunk, but they said they were staying out so they wouldn't have to drive home), and my sister was at a sleepover.
Naturally, I invited Tara over.
I don't want to detract from the focus of this story any more than I already have, but what happened with Tara reminded me quite a bit of the girl from when I was sixteen. Not the sex on my bed part, or the shower together where we played with each other quite a bit, or the fucking her ass as she bent over my parents' bed and spread herself open for me, or the spanking her with a metal spatula -- she took two whacks and made me stop, but then, I'd already used my hand over the seat of her shorts and her panties, and a belt on her bare ass. No, it was after I'd filled her ass with my come and we were sprawled out on my bed.
I started to feel a little worried. Bad, even. That I had done something wrong by having casual sex with this woman -- but then, I'd done the same thing with Diana and hadn't felt bad at all, especially after Saturday morning's orgasm.
I couldn't shake the feeling. I found a way to politely ask Tara to leave -- in other words, called the house phone from my sister's phone and said I had to go pick my sister up from her friend's house, because she wasn't feeling well. Tara and I kissed and hugged -- rather less chastely than Diana and I had only six weeks or so prior -- and she left. We talked a few more times, and then I went back to college.
It bears mentioning that during the next summer, Tara and I had two more liaisons -- one at my house, where we fucked in the pool, in the shower, and in bed, and then I took her out to lunch; the other at her house, which was spent completely naked and involved, among other things, being introduced to her shaved pussy, spanking her with my hand and a belt and a paddle, offering to let her spank me (she refused), fucking her pussy, fucking her ass, coming on her face (her idea), and relaxing on her couch. She actually met me at the door naked, as I'd instructed, telling her that if she did so, I would immediately spank her, hard and fast. She preferred the anal sex to the spanking, but given how much she loved getting spanked, it's easy to imagine how much more she loved taking it in the ass.
And Tara, if you're reading this -- I'm sorry about that New Year's Eve thing. I feel even worse about it, if you can believe that.
Now that I've covered the Tara angle, I don't wonder if I shouldn't delete it all and just continue with Diana. But Tara was an important part of my sex life, and I look back with great fondness on every single intimate thing we did -- though if I could do it again, I'd have fucked her ass in the shower that night, instead of on the bed. Without having had those two nights with Tara -- New Year's Eve, and about a week before, the night we met, during which I got her off with my hand and she sucked me off with a fervor that I can only call religious in its intensity -- this story might have ended after Diana said goodbye on that Saturday.
But it didn't.
I got an e-mail about a week after I got back to school. It was from Diana. I can't remember exactly what it said, but it invited me to spend a long weekend -- Friday to Monday -- in Illinois with her. She had some free flight vouchers from TWA, and wanted me to come visit.
Needless to say, I said yes. Immediately. I had just gotten a job -- made up a good excuse to get out of it -- and had just had some intimate moments the week before, but that didn't stop me from asking my roommate to drive me (in my car, since he didn't have one) to the airport and pick me up again when I got back.
The intimate moments? Not necessarily sexual. Not all of them. Two weeks before I was to leave, I invited a very nice girl named Maria out to see The Crucible -- the Daniel Day-Lewis version. We both enjoyed the movie greatly, and thankfully, when I blew my nose and the tissue redirected a little something flying out and onto the dashboard, she didn't notice. We sat in her room for hours after we got back, but I left without a kiss, just a hug and the vague assertion that we should do it again.
The next weekend was the Superbowl. The Packers won it, I remember that, but the weekend was more special because it was the weekend during which I met the woman who is now my wife. We kissed within three hours of meeting, and stayed up almost all night talking. She isn't prudish now, but she had very little experience back then and it was nothing short of amazing that she took off her top and her bra and let me touch her breasts. I was spoiled at that point by Diana's -- my not-yet-wife's are large, but they don't have that perfect shape, and Maria's were probably very nice, though they were quite small. Not that I minded.
Digressing again.
On Friday morning, I packed my things and my roommate drove me to the airport. Quite a long way to go to get to that point, but what could I do? This isn't a fearless and searching moral inventory, but it's creative nonfiction, and that means it's hard to tell where to stop and where to go off on tangents.
The flight to St. Louis was about two hours plus a time change. I spent most of it reading. Diana had set up a voicemail drop with an 800 number, so before I took off, I called it to let her know when the plane was leaving. She lived in Springfield, and would be driving to St. Louis to meet me.
This was before 9/11. Diana was able to meet me at the gate. She was as pretty as I remembered, and we hugged and she kissed my cheek before we went down to the baggage claim.
But something was different. I couldn't put my finger on it. Maybe it was that she was letting me into her life in a way none of the other men she knew had been let in. Maybe she was feeling ill. I didn't know then, and I don't know now. But I didn't pay much attention to it; I simply collected my bag -- brought five condoms this time -- and we got in the car and took the long, boring two-hour drive to Springfield. I suppose we talked on the trip, but I can't remember what we discussed.
I met Diana's roommate -- whose name I can't remember, so let's call her Kate -- and got myself set up in Diana's bedroom. I met her dog, a nice little Dachshund.
Then we had to figure out what to do with ourselves.
We ended up taking her dog to PetSmart -- he had little boots; it was just above freezing all weekend -- and then going out to Friday's for dinner. She paid; I made no bones about the fact that I had no spending money to spare.
I think things got a little chillier then.
In 1997, I was still wearing pajamas, so to speak; I had a roommate who slept in the same room, so I was all about modesty. I was a little more confident after my adventures with Tara and Diana, my few dates, and my burgeoning relationship, but I had no desire for my roommate to see me naked, nor vice versa. I pulled on a t-shirt and a pair of shorts and climbed into bed beside Diana. We didn't cuddle, we didn't touch, we just kissed goodnight and went to bed.
Not an auspicious start.
Saturday lasted almost twenty-four hours -- 8 a.m. to 4 a.m. (Sunday morning) -- and it was some of the most unpleasant time I can remember having.
The day started well enough; we had breakfast with Kate and Kate's cat. We took the dog to the park. We had lunch. We went to Jewel/Osco and picked up some snacks and mudslide mix. And kahlua. I remember kahlua.
We got home around two and decided to watch First Knight, which Diana had rented. She made the mudslides, we evicted the dog from the room, and we cuddled up to watch the movie, me behind her.
I didn't much care for the mudslide, and it put me to sleep for the second half of the movie. I woke up shortly after it ended; perhaps Diana was touching me to wake me up, I don't know. But we began to kiss and, at some point, our clothes ended up on the floor.
Again I failed to distinguish myself as a lover. I paid more attention to her breasts, but to the exclusion of other body parts, and I didn't even think to go down on her. I tried to get her off using my fingers, but I couldn't seem to find the right spot.
Both Diana and I were getting frustrated, and somehow I ended up on top of her, inside her, unprotected.
I had had unprotected sex before -- with Mary; as stupid as it was, we mostly depended upon pulling out, and when I think back on it, I cringe to think how lucky I was to not get her pregnant.
Without the condom, though, Diana -- one of the most responsive lovers I have ever had, before or since -- was way, way too good for me to hold on.
No chance in hell I was going to come inside her, though.
But I was close. Too close.
I grunted and pulled back, just in time, but I lost my balance and my right hand came down hard on the bed, brushing stiffly against a bad bruise on Diana's side -- I don't remember what happened, but she'd told me she had it and that I should be careful of it.
While she hissed and rolled, I slid down off the bed, hoping I could put on a condom and get Diana back in the mood, but the moment I touched my cock, I lost control and came against my palm, barely able to catch it all.
Thank goodness for the shirt I'd slept in the previous night. I told Diana I twisted my ankle and, having used that lie quite a lot in high school to get out of… well, lots of things… I was good at faking it.
The sex, though, had been a miserable failure, and it was mostly, if not completely, my fault.
Diana and I dressed in silence and I walked the dog. When I came back, she said she'd gotten a call from work.
"I have to go in Monday," she said. "Do you mind if we change your flight to tomorrow night?"
I had no idea that was even possible, but I said that was fine and she called and took care of it. I called my roommate and told him I was coming back Sunday night, and he said he'd pick me up as we arranged.
I think that helped matters. We were talking again, and we went out to a light dinner and then to see the remastered Episode IV. We were geeks.
After the movie, we talked for a while before going to bed. The conversation, I seem to recall, was mostly facile -- comparisons between the new and the old versions, what might change in the next two films, that sort of thing. We changed into our pajamas with no modesty at all -- I very much appreciated her body even during the mundane actions of dressing and undressing -- and went to bed. There was a chaste kiss, I believe on the lips, but that was it.
I thought the night was over, but I was wrong.
I woke at about two with severe stomach cramps, and climbed carefully over Diana to go to the bathroom -- the only bathroom in the little house she and Kate shared.
Yes. It went exactly as bad as that.
"Hey."
"Huh?" Diana was completely out of it.
"Your bathroom's broke. I need to get something to fix it. Can I have your keys?"
"Dr… esser…"
She was asleep before I had even gotten halfway dressed, and I got the hell out of the house, hoping to pick up what I needed and get back before either Diana or Kate woke up and needed to use the bathroom.
I have always had a good head for directions, and though I accidentally ran several red lights -- in that part of Springfield, the lights were on poles on the corners, instead of hanging over the intersections -- I made it to Jewel/Osco without incident.
It was freezing -- no warmer than twenty degrees -- and I was so concerned with getting into the store that I didn't look where I was going.
Foot on ice.
Me on ass.
Knee on fire.
Oh.
Shit.
It was an extremely mild twist -- I wasn't even limping by the time I paid for the plunger and got back to the car -- but it had scared the hell out of me. My parents didn't know I was in Illinois, and if I'd been taken to the hospital, not only would they have found out I was halfway across the country without their knowledge, but Diana and Kate would know what I had done to their toilet.
Go ahead and laugh. I'll wait.
Done? Good.
It took about an hour to fix the toilet -- the water pressure was extremely low in that house -- and throughout the entire ordeal, Kate's cat watched me from up on the counter as I sat on the floor, waiting for the water to go down or the tank to fill. I climbed into bed about four and passed out.
The ride back to St. Louis was quiet. I stared out the window for most of it. Diana dropped me off at the departure doors for TWA, gave me a hug, and was gone before I was inside the terminal building. I read some books for English Comp II on the flight back, and my roommate and his girlfriend were waiting at the airport, holding up a little handwritten sign with my name on it.
I e-mailed Diana when I got back to the dorm, but I never got a response.
I never saw Diana on AOL again, not under either of her screen names.
I sent her several e-mails, none of which were returned.
I even sent her a Christmas card.
But that hug was the last touch I ever got from Diana, and watching her get into her car… that was the last time I saw her.
That's the whole sordid story. One good evening, one amazing morning, one dismal failure of an afternoon, and one vastly unpleasant overnight. But if I omitted certain details in the telling, I discovered that my fraternity brothers were completely blown away by the story. Until I showed them the flight vouchers and some photos I had taken, not a one of them believed the story.
Now it's a legend. The new brothers, the ones who've been initiated after I left the college, are often told a version of this story, and they're all amazed.
It's nice to have a legacy. Maybe when I set out the official story to the next crop of brothers -- which I'll probably do during Alumni Weekend later this year or early next year -- it might lose some of its luster, but really, how many eighteen-year-olds can say a woman flew them more than one thousand miles just to have sex?
Or, as the brothers call it, "The Legend of Listener's 1,000-mile Booty Call".
Diana, if you're reading this, I'm sorry for what happened that Saturday in 1997, and I'd really like to talk to you, to apologize directly. If I could do it again, you can imagine what I'd change, and I'm sure you can imagine what would stay the same. You were a part of my life that I don't regret for a second -- except for that moment when I hurt you, and what happened early Sunday morning, but I think you can understand that.
And even if you don't reach out to me, know that I think fondly of our time together, and if my choice was losing it all or keeping it exactly as it is, I would choose the latter without hesitation.
*****
7760 words.
Feel free to review. I'll be posting more "Shell Game" in a few days, if I have time, but this story just started pouring out and I had to finish it, to the exclusion of posting more "Shell Game". Like I said, it's a true story, as unflinchingly-accurate as I could make it. I'm sure similar things have happened to at least some of you.
Think of it as a confession. I have confessed. Now back to our usual BDSM-flavored smut.
The True Story That Made Me A Legend
(at least, among my fraternity brothers)
*****
Warning: this is creative nonfiction. That means I'm looking back on it while being older and wiser, and I can't remember every detail exactly. To the best of my knowledge, this is as close to the truth as I can remember, except for changing 90% of the names.
This story contains sexual practices that may be considered unsafe. Always use protection.
*****
At 18, I wasn't what you'd call outgoing. I was in a new place, just starting college, and all my attempts to be the cool guy failed. Miserably. I was still just another geek -- a geek with other geeky friends, and some not-so-geeky friends who, like me, were in the Honors program -- but I wasn't the cool guy I wanted to be.
I think, in retrospect, that hanging upside-down over the back of a couch while at a mixer for my dorm might not have been the best option.
I actually have some pretty good memories of my freshman year at college. Aside from my ex, Crazy Mary, breaking up with me over the phone and eventually writing a chapbook about the guy she left me for, it wasn't bad at all. I met a lot of great people who are even now sitting on my Facebook and MySpace pages, waiting for me to go send them messages. And in my second semester, I met my wife -- of course, at the time, she wasn't my wife, but that's neither here nor there.
I also met Diana.
When I was in high school, I spent a lot of time online, mostly on ChatLink-affiliated BBSes or the BBSes I cosysop'd. Even when I was dating Crazy Mary -- she who took my virginity in the backseat of my car as it sat in my driveway, hidden by a car cover -- I still spent hours talking to all sorts of people, most of whose real names I never knew. In college, though, I didn't know about any BBSes.
My mom had AOL. I had her password.
You can guess what happened next.
Hey, I was eighteen. Not my fault I downloaded lots of porn.
Even at eighteen, I was already a kinky person -- or, at least, I thought I was. Mary and I had had anal sex a few times, and though she didn't care for it and I never actually came in her ass, I had enjoyed the few moments of exceptional tightness that act provided. I've since done it with two other women, and neither held me as strongly as Mary did.
As for BDSM? Mary allowed me forays into that as well. I spanked her on several occasions, a couple of times to the point where her ass actually was almost red. She never really complained, I think because she was afraid I'd leave her if she said no.
I wouldn't have.
I also put a collar and leash on her once or twice, for shock value, leading her around by it (she was walking, not crawling) while we hung out with our friends. I verbally dominated her from time to time, ordering her to remove various items of clothing, walk to my house without underwear, wear certain outfits I thought looked good on her, and once or twice having her show her breasts while we drove. Always at night, but there was still the thrill of danger, of someone seeing.
I was drawn to kink even then. When my friend Amy said her boyfriend spanked her -- it came up in conversation legitimately, don't ask me how -- I asked her, "in what way?" She stuck out her hip and slapped it.
That night, I wrote a fairly-crappy short-story about how I really wanted to handle that moment -- to invite Amy back to my house and give her a real spanking. I never did, and now Amy and I are very good friends who never discussed that moment again. She's on my MySpace page too.
So with all this kink floating around, it's no surprise that I spent a lot of time on AOL's newsgroup reader, chatting on the A.S.S. board (before it became S.S.S.), and also in AOL's D/s chatrooms. I tried not to be That Guy, the one who instantly IM'd anyone with "female" in their profile. Instead, I talked to people. Guys and girls.
Which is how I met Diana.
I don't know what Diana was expecting when she talked to me those first few weeks. All I know is that she was twenty-nine -- eleven years older -- and that we had some common interests. She liked sci-fi, BDSM, and good books, just like me. I suppose our ages came up at some point -- I didn't have mine in my profile because I wanted to be judged on who I was, not how old I was -- but once Diana learned I was a legal adult, I guess nothing else mattered.
Or maybe she knew I would just end up being a one-night stand.
In October, Diana mentioned that she'd be making a trip along the eastern seaboard to visit friends, and wanted to know if I wanted her to stop in Orlando. At that point, I had no idea of what might happen, but I had hopes. I hadn't had sex since Rosh Hashanah, my whirlwind 36-hour trip back home -- Mary, only five days before breaking up with me, had let me fuck her in my backseat as the car nestled hidden in a loading dock behind what is now a Home Depot. It had been good sex, though somewhat unfulfilling; we both came, but I'd had to pull out before I did and when she jacked me off, I spurted so hard that it hit the side of my mouth.
Like I said, it had been a while, especially since, before I moved away, Mary and I had been having sex at least twice a week.
But Mary broke up with me and I didn't have any prospects on the horizon. No real ones, anyway. Marianne was on the crew team and didn't have time; Gina was way out of my league and had a long-distance boyfriend in any case; Hope was hopelessly devoted to my roommate in the hopes that he would ask her out; and Bella was the object of my suitemate's affections, thereby putting her in "don't ask her out if you don't want to piss off your friend" territory. There were other girls in my network, so to speak, but none I really thought I had a chance with.
The idea of possibly sleeping with Diana had its perks. Sleeping with… and more… especially since she was twenty-nine and would be getting a hotel room.
I have since had sex in a dorm room. It was very difficult to keep quiet, but it helped that my roommate slept like the dead.
But I digress.
In 1996, there was no cheap and easy digital photography. Photos had to be scanned, a time-consuming process made more so by the lack of good plug-and-play. Neither Diana nor I had seen photos of each other; I would know who she was by the color of her car, by her license plate numbers, by the fact that she was five-foot-six and blond, by her glasses in conjunction with all of that.
In return, I told her my height, that I was kind of a big guy, that I would be wearing a certain pair of jeans and a certain shirt.
We had plans to go see Star Trek: First Contact; it wasn't like I needed to dress up. As much as I wanted Diana to take me to bed, I had no expectations.
I gave Diana directions to the parking lot outside my dorm -- now itself another dorm building; parking at my college was always bad, but when I finally left after getting my Master's in 2002, it was nigh-impossible -- and waited for her call. She was coming down I-95, and when she got to a certain exit, she would call me -- this was before cell-phones too, technically, and neither of us owned one -- so I would know where she was.
She called at 4:00.
I was showered, shaved -- obsessively trimming my goatee until it got so messed up that I finally just sheared the damn thing off -- and dressed at least forty-five minutes before she was to show up.
And I couldn't do anything else. I tried to read, tried to study, tried to work on a paper, but nothing worked. I ended up relaxing on my bed, watching a show I'd taped, only half paying attention.
It did help. The clock moved, and 5:15 eventually came.
I went downstairs, heart hammering, not even entertaining the thought that Diana might be an AOL-meeting-from-hell-in-the-making. Such things hadn't even hit the news yet. There was no way Diana wouldn't at least be passably pretty -- at that age, that was still more important to me than who she was, and I'm really quite embarrassed to admit it.
Fortunately, her appearance was not a problem. Not at first, and certainly not later.
"Hi."
I held out my hand. "Hello." My voice didn't crack, thankfully. "It's nice to meet you."
"Nice to meet you too." She pointed at the car. "Should we go? The movie's in twenty minutes."
I nodded and got in; she went around to the driver's side and, after buckling up, I started giving her directions to the theater.
I did manage to avoid staring, but then, Diana was… well, there's no nice way to say it. She was plain. Not unattractive by any means -- to this day I still have a few photos of her laying around -- but nothing terribly special. The eighteen-year-old me took note of the fact that she had fairly-large breasts, try as she might to hide them under a t-shirt and a flannel. She wasn't fat, but wasn't thin; her face was a rounded oval -- the tall kind, not the wide kind -- and her hair, while blond, could have probably used a little work. Her hair fell halfway between her chin and her shoulders -- shorter than long, but longer than short. If I'd met her today, I'd have said her jeans were flattering, but that's with the benefit of having since seen her naked. They made her ass and her legs look good.
But one thing about Diana made her, for the moment, the most attractive woman in the state of Florida:
She was interested in hanging out with me.
We both enjoyed the film -- First Contact is arguably one of the top three Star Trek movies, possibly even one of the top two, although I prefer II and VI to VII any day. Afterward, though, Diana said she wasn't feeling so well and wanted to lie down. We went back to the hotel and I told her I would walk over to the plaza and pick up dinner.
It was McDonald's, but then, I had asked her what she wanted, and I was too naïve to know that when a woman says that, it's not really what she wants to eat. The food helped her feel a little better, though, and by 9:00 we were staring awkwardly at each other, her on her stomach on the bed, feet by the pillows, and me on my knees, face close to hers.
I don't remember who kissed whom. It was a nice kiss, not terribly memorable as kisses go but not bad at the time. It made me acutely aware of the fact that I had two condoms tucked in the back of my wallet, two of a supply that hadn't been replenished since before I came to college. Had they reached their best-by date, I don't know what I would've done -- probably not even brought them, and missed out on this -- but they still had eight months left, so I felt safe enough.
We kissed for a while, moving up onto the bed, hands wandering across each other's bodies. I discovered that it was indeed possible to have breasts that large that were also firm -- though I didn't see them at the right angle until later, I could tell they had that perfect shape that breast connoisseurs and horny teenage boys covet. She was -- still is, I'm sure -- at least a D-cup, possibly a DD, but there was barely any sag.
I didn't pay enough attention to them. Or to her neck, or her arms, or any other part I would normally lavish attention upon. I was too busy working my way down, working her out of her jeans and me out of mine. I must recall with some dismay that, at the time, I had not yet discovered the joys of boxer shorts, so you can imagine what the state of my underwear was.
Could've been worse; I don't even remember hers. I just remember kneeling at the foot of the bed, hiding my body, hiding the fact that I was overweight and that, without my shirt on, I was incapable of feeling attractive to anyone. Her sex was right in front of me, covered by her panties -- I think they were pink -- and I knew with every part of me that I was going to get to fuck this girl.
No. That wasn't right.
I was going to have sex with, possibly even make love to, a woman.
To this point, all of my sexual experience had been concentrated within the eleven months I dated Mary, and one fumbling evening with a nice but as-overweight-as-me girl I met when I was sixteen. Everyone before Diana… they were girls.
I couldn't possibly call Diana a girl. It would've been a slight that, had I done so, I might never have recovered from making.
Luckily, there was something else on my mind.
"Is there anything…" I swallowed hard, willing myself not to blush. "Anything I should… um… know?"
The ultimate question in the age of casual sex: do you have any sexually-transmitted diseases? Only this was my first time having casual sex. I had no idea how to ask the question. When I met my wife, she told me flat out that she was a virgin and had had very little sexual contact, but I had a level of comfort with her that I didn't have with Diana. I was intimidated by her, and more than a little; she would be my first casual sex experience, my first real one-night stand -- the girl when I was sixteen didn't count; we got naked, and then I made up an excuse to end the encounter -- and I didn't want to fuck it up.
Diana knew what I was asking. She gave me an answer that unquestionably equated to "no" without making me feel bad for asking.
That was when I took off her panties and began to touch her.
Ann, my first serious girlfriend, had been quite prudish, only allowing me to suck her breasts with my eyes closed, and I had obeyed her wishes. Our courtship had been rather sweet -- four mis-timed kisses at a youth center in Miami, more kisses the next day, sleeping in the poolhouse while she stayed in her bedroom, and on several occasions, my hands finding their way into her shirt.
And below.
I don't think I took advantage of Ann -- she was a few months older than me, though I definitely had more experience -- but I know for a fact she didn't know how to react when she permitted me to put my hand down the front of her clothes and touch her. She enjoyed it, but she never came. And I never saw what I was touching. No, Ann was too much of a prude to actually take off her shorts -- or, on one amazing weekend, to let me lift her nightgown enough to see her sex.
The overweight girl was shortly after Ann and I broke up -- it had been her idea, citing the hour-long drive between her house and mine and the fact that neither of us had a car or a license -- and my hands never went below her waist before I lost my nerve.
Mary had taken charge that first night, and as we sat in my backseat and kissed, as I fondled her breasts -- so much bigger than Ann's, so much softer -- and played with her neck and let my hand creep up her thigh to push her panties out of the way and find her clit… I'm sure that sentence was going somewhere, but the memory is too intense. Mary may have come; I didn't know her well enough to know if she did or didn't. I do remember, though, that she had quite a bit more hair down there than Ann had -- at least, according to what my hand was telling me -- but then Mary was more developed than Ann and for all I knew at the time, hair in that area was directly related to breast size.
Having never been both naked and intimate with a woman whose breasts were smaller than a C-cup, I still don't actually know the answer.
I had plenty of opportunity to get to know Mary's breasts, sex, ass, legs, stomach, shoulders, and all more mundane parts as well. And while I did love her, I didn't really love that she had apparently never gone farther than soap and water when grooming between her legs. Giving her head meant getting hair caught in my teeth. I did the best I could, but while I think completely shaving is a little disturbing, that much hair comes with its own problems.
Even though it hadn't happened when I knew Diana, I have to mention Tara, who I slept with several times toward the end of 1996 and in the summer of 1997. To this day, Tara is the only partner I've ever had who's completely shaved, and while it was an odd experience, what I disliked about wasn't the way it looked.
It was the way she smelled. Or, more precisely, the way her lotion smelled. To cover what she must have thought was an unpleasant scent, Tara used a strawberry-melon-scented lotion, and that was all I tasted as I knelt at the foot of her bed and brought my mouth to her clit. Had Tara not been so very responsive and so very into getting eaten, I might have given up.
Even giving up after a few minutes would've been more than I did for Diana. No, I was still so blown away by the very idea of seeing Diana naked, of sleeping with her, that I only used my hands on her until, by some unknown signal, she indicated that I should be on top of her, be inside her.
Condom? Check. And I even got it on in the right direction, which is a real pain when doing it by touch.
Our bodies joined easily. She arched to take my cock inside her, her sex warm and wet, so wet that I felt the slickness through the condom. Or so it seemed.
I can't complain about the sex, not really. It was good. Not as good as my first time -- Mary took my virginity, and I was so overwhelmed that I held back my orgasm for a good ten minutes, enjoying every second and every sound and every sensation -- but still good.
Too good.
Diana was a woman. I'd only been with girls before.
Diana was responsive. My cock had never elicited this kind of response from Mary.
Diana was going to come, and soon. But not as soon as I was.
I'd found a rhythm she enjoyed, one that made her moan and clutch at my shoulders. Unfortunately, it was also a rhythm that brought me so close to coming that I couldn't hold on, and though I didn't do anything stupid like hold up her legs and hammer into her, I know that toward the end I was moving quite fast in and out of the hot, clinging flesh of her sex.
It took everything I had to keep going afterward, even as my greatest fear leached away my erection -- that I had failed to satisfy this beautiful woman who seemed to want nothing more than to watch Star Trek and fuck me.
Diana had been close enough when I came that, only a couple of seconds after my last feeble twitch, she flew over the edge and joined me.
As I reflected on that moment in later years, I became more and more convinced that, while she'd most definitely enjoyed the sex, that hadn't been a real orgasm.
I have two reasons to say that.
First, we had sex twice more after that. She wouldn't have wanted me to be with her again if I'd been a complete fuck-up.
Second… well… that takes a little more explanation.
I had made Mary come on several occasions. Most of the time, in fact. I made it a point of pride, especially after reading so many online accounts -- most of them fiction, I'm sure -- of how women had been left unsatisfied by their men. I didn't want Mary to leave me for that reason.
I was dorky, I was fat, and I didn't have a lot of friends. Didn't do much for my self-esteem. College helped -- Diana helped -- but my senior year in high school was fraught with insecurity and the last thing I needed was to be dumped because I was no good in bed.
So I learned what Mary liked. I learned how she liked to be touched, how she liked to be kissed, how I should use my hands and how that differed from the way I used my mouth or my cock. Mary came. A lot. Not the copious-orgasm type of a lot; I mean in terms of frequency.
Mary was one of those girls who has one big orgasm and then is done for the night -- or at least for an hour or two -- and is fully able to concentrate on pleasing her partner. My wife is like that too, except she tends to be so languorous after coming that -- and I would say this is the case about seventy percent of the time -- by the time she gets her strength back we've been fucking long enough that I'm out of stamina.
Diana may have been one of those women. It may just have been the fact that she would be leaving in a few hours that changed the way we had sex the second time. I can't answer the question -- and I don't remember her last name, unfortunately, so I can't even look her up on the 'net.
But I'm glad to say that the second verse was nowhere near the same as the first.
I'd been woefully unprepared to spend the night in Diana's hotel room. I had my condoms, but no change of clothes, no toothbrush, no deodorant, no comb.
Diana didn't seem to care. I think it was me who woke her up as I came back from the bathroom. We kissed and snuggled together, naked under the covers, sharing warmth and the closeness that comes with waking up next to someone and realizing you're not regretful at all about the previous night.
For a moment, I actually entertained the thought of being in a relationship with Diana, of having her next to me every night. It was a pleasant thought -- her body was soft and smooth, her breasts were nothing short of spectacular, she felt good in my arms and fit well against me, and she'd seen me naked and wasn't completely repulsed.
The fact that we started to touch a little more insistently was proof of that. I found the second condom -- again with very little foreplay, either me to her or her to me -- and got it in place on my cock.
I was on my back.
And in a few seconds, she was straddling me, riding me, hot and tight, head thrown back, breasts so firm they seemed to barely move. I was mesmerized by them. I touched them, caressed them, pinched her nipples gently -- knowing somehow that treating them like radio knobs would be a bad thing -- but she didn't lean down far enough for me to kiss them. Or her.
But here was a beautiful woman riding my cock, bouncing up and down, making noises that said she was beyond happy.
It was heaven.
There was no way I would let myself come before Diana, not this time. I would not let her go back to Illinois thinking I was a selfish lover.
As she slid up and down on my cock, I worked my hand between our bodies and found her clit.
If I'd had any doubt before that I was pleasing her, this removed it completely. I felt the first stirrings of orgasm, that little tightening deep in my lower stomach, but when she came, I completely forgot about it.
Because when Diana came, she came.
My hands on her hips.
My cock gripped tight inside her body.
Her nipples small and hard on those glorious breasts.
Her head thrown back, then thrown forward.
Her thighs going stiff.
Her mouth opening.
And a noise that, to this day, I can't begin to describe, mostly because I don't remember it.
I was too lost in the feeling of her orgasm cascading down around the base of my cock, around my balls, a puddle spreading under my ass.
And too lost in the wonder of it to realize that she was riding me again, harder, faster, our bodies slapping together, my hips rocking up to meet her and falling back to squelch in the wetness soaking the sheets until I dug my fingers into the bedding and groaned her name and came and came and came…
Diana took a shower while I recovered, and by the time she got out, I was already dressed. That gave me the luxury to watch her put her clothes on, and it also let me observe her perfect breasts in their natural habitat, so to speak; that is, as she walked around, doing all the small things people do to get dressed after a really good fuck.
They really were absolutely flawless. I have never seen more perfect breasts before or since, except maybe after the application of Photoshop.
Once dressed, she drove me back to the dorm -- only a five-minute trip, as the hotel was right across the street from the college -- and after taking a few pictures, we said our goodbyes. Hugs, chaste kisses, and promises to e-mail and call, and then she was in her car and out of my life.
Back in my room, I changed my clothes, washed up, brushed my teeth, had a little something to eat, and tried very, very hard not to think about whether or not Diana had done this before, and whether or not she would do it again. She did say she was going up and down the eastern seaboard, from Virginia to Florida and back again. For all I know, she had fucked all her friends in all those other states, and was even now on her way to fuck someone in Miami or Tampa or Key West.
That afternoon and evening, we helped my roommate's friend Alfred move to a new apartment. It took my mind off things. The next day I sent Diana an e-mail -- though it was over AOL, so maybe it didn't really count -- and about a week later, I got a response: she was back home, everything was fine, it was great to see me, hoped to see me again, that sort of thing.
It made me feel good.
But not as good as what happened next.
This story would not be complete if I didn't mention what happened over winter break. In short, I arranged a meeting with Tara -- she of the shaved pussy, though it wasn't shaved when I met her -- after we chatted on AOL. She got my attention by sending me an IM and asking if I was into anal sex.
Even if I hadn't been, what eighteen-year-old in his right mind would say no, especially to a twenty-three-year-old woman asking him that question out of the blue? Again, this was before the days of internet dating horror stories, so when she told me what she looked like, I believed her.
I went into the meeting with no expectations -- we were to meet at a bookstore, a safe place, at the self-help section. She told me she was five-eight and about 180 pounds, and that she had blond hair and blue eyes. I sound shallow when I admit this, but I was a little disappointed when I met Tara -- she was at least forty pounds north of her stated weight. I wasn't disappointed at her appearance, though; I was disappointed that she lied.
Tara has appeared in various forms in various stories I've written, so I won't go into a lot of detail, except to say this: on New Year's Eve, my parents were out partying (probably at a friend's house, getting high or drunk, but they said they were staying out so they wouldn't have to drive home), and my sister was at a sleepover.
Naturally, I invited Tara over.
I don't want to detract from the focus of this story any more than I already have, but what happened with Tara reminded me quite a bit of the girl from when I was sixteen. Not the sex on my bed part, or the shower together where we played with each other quite a bit, or the fucking her ass as she bent over my parents' bed and spread herself open for me, or the spanking her with a metal spatula -- she took two whacks and made me stop, but then, I'd already used my hand over the seat of her shorts and her panties, and a belt on her bare ass. No, it was after I'd filled her ass with my come and we were sprawled out on my bed.
I started to feel a little worried. Bad, even. That I had done something wrong by having casual sex with this woman -- but then, I'd done the same thing with Diana and hadn't felt bad at all, especially after Saturday morning's orgasm.
I couldn't shake the feeling. I found a way to politely ask Tara to leave -- in other words, called the house phone from my sister's phone and said I had to go pick my sister up from her friend's house, because she wasn't feeling well. Tara and I kissed and hugged -- rather less chastely than Diana and I had only six weeks or so prior -- and she left. We talked a few more times, and then I went back to college.
It bears mentioning that during the next summer, Tara and I had two more liaisons -- one at my house, where we fucked in the pool, in the shower, and in bed, and then I took her out to lunch; the other at her house, which was spent completely naked and involved, among other things, being introduced to her shaved pussy, spanking her with my hand and a belt and a paddle, offering to let her spank me (she refused), fucking her pussy, fucking her ass, coming on her face (her idea), and relaxing on her couch. She actually met me at the door naked, as I'd instructed, telling her that if she did so, I would immediately spank her, hard and fast. She preferred the anal sex to the spanking, but given how much she loved getting spanked, it's easy to imagine how much more she loved taking it in the ass.
And Tara, if you're reading this -- I'm sorry about that New Year's Eve thing. I feel even worse about it, if you can believe that.
Now that I've covered the Tara angle, I don't wonder if I shouldn't delete it all and just continue with Diana. But Tara was an important part of my sex life, and I look back with great fondness on every single intimate thing we did -- though if I could do it again, I'd have fucked her ass in the shower that night, instead of on the bed. Without having had those two nights with Tara -- New Year's Eve, and about a week before, the night we met, during which I got her off with my hand and she sucked me off with a fervor that I can only call religious in its intensity -- this story might have ended after Diana said goodbye on that Saturday.
But it didn't.
I got an e-mail about a week after I got back to school. It was from Diana. I can't remember exactly what it said, but it invited me to spend a long weekend -- Friday to Monday -- in Illinois with her. She had some free flight vouchers from TWA, and wanted me to come visit.
Needless to say, I said yes. Immediately. I had just gotten a job -- made up a good excuse to get out of it -- and had just had some intimate moments the week before, but that didn't stop me from asking my roommate to drive me (in my car, since he didn't have one) to the airport and pick me up again when I got back.
The intimate moments? Not necessarily sexual. Not all of them. Two weeks before I was to leave, I invited a very nice girl named Maria out to see The Crucible -- the Daniel Day-Lewis version. We both enjoyed the movie greatly, and thankfully, when I blew my nose and the tissue redirected a little something flying out and onto the dashboard, she didn't notice. We sat in her room for hours after we got back, but I left without a kiss, just a hug and the vague assertion that we should do it again.
The next weekend was the Superbowl. The Packers won it, I remember that, but the weekend was more special because it was the weekend during which I met the woman who is now my wife. We kissed within three hours of meeting, and stayed up almost all night talking. She isn't prudish now, but she had very little experience back then and it was nothing short of amazing that she took off her top and her bra and let me touch her breasts. I was spoiled at that point by Diana's -- my not-yet-wife's are large, but they don't have that perfect shape, and Maria's were probably very nice, though they were quite small. Not that I minded.
Digressing again.
On Friday morning, I packed my things and my roommate drove me to the airport. Quite a long way to go to get to that point, but what could I do? This isn't a fearless and searching moral inventory, but it's creative nonfiction, and that means it's hard to tell where to stop and where to go off on tangents.
The flight to St. Louis was about two hours plus a time change. I spent most of it reading. Diana had set up a voicemail drop with an 800 number, so before I took off, I called it to let her know when the plane was leaving. She lived in Springfield, and would be driving to St. Louis to meet me.
This was before 9/11. Diana was able to meet me at the gate. She was as pretty as I remembered, and we hugged and she kissed my cheek before we went down to the baggage claim.
But something was different. I couldn't put my finger on it. Maybe it was that she was letting me into her life in a way none of the other men she knew had been let in. Maybe she was feeling ill. I didn't know then, and I don't know now. But I didn't pay much attention to it; I simply collected my bag -- brought five condoms this time -- and we got in the car and took the long, boring two-hour drive to Springfield. I suppose we talked on the trip, but I can't remember what we discussed.
I met Diana's roommate -- whose name I can't remember, so let's call her Kate -- and got myself set up in Diana's bedroom. I met her dog, a nice little Dachshund.
Then we had to figure out what to do with ourselves.
We ended up taking her dog to PetSmart -- he had little boots; it was just above freezing all weekend -- and then going out to Friday's for dinner. She paid; I made no bones about the fact that I had no spending money to spare.
I think things got a little chillier then.
In 1997, I was still wearing pajamas, so to speak; I had a roommate who slept in the same room, so I was all about modesty. I was a little more confident after my adventures with Tara and Diana, my few dates, and my burgeoning relationship, but I had no desire for my roommate to see me naked, nor vice versa. I pulled on a t-shirt and a pair of shorts and climbed into bed beside Diana. We didn't cuddle, we didn't touch, we just kissed goodnight and went to bed.
Not an auspicious start.
Saturday lasted almost twenty-four hours -- 8 a.m. to 4 a.m. (Sunday morning) -- and it was some of the most unpleasant time I can remember having.
The day started well enough; we had breakfast with Kate and Kate's cat. We took the dog to the park. We had lunch. We went to Jewel/Osco and picked up some snacks and mudslide mix. And kahlua. I remember kahlua.
We got home around two and decided to watch First Knight, which Diana had rented. She made the mudslides, we evicted the dog from the room, and we cuddled up to watch the movie, me behind her.
I didn't much care for the mudslide, and it put me to sleep for the second half of the movie. I woke up shortly after it ended; perhaps Diana was touching me to wake me up, I don't know. But we began to kiss and, at some point, our clothes ended up on the floor.
Again I failed to distinguish myself as a lover. I paid more attention to her breasts, but to the exclusion of other body parts, and I didn't even think to go down on her. I tried to get her off using my fingers, but I couldn't seem to find the right spot.
Both Diana and I were getting frustrated, and somehow I ended up on top of her, inside her, unprotected.
I had had unprotected sex before -- with Mary; as stupid as it was, we mostly depended upon pulling out, and when I think back on it, I cringe to think how lucky I was to not get her pregnant.
Without the condom, though, Diana -- one of the most responsive lovers I have ever had, before or since -- was way, way too good for me to hold on.
No chance in hell I was going to come inside her, though.
But I was close. Too close.
I grunted and pulled back, just in time, but I lost my balance and my right hand came down hard on the bed, brushing stiffly against a bad bruise on Diana's side -- I don't remember what happened, but she'd told me she had it and that I should be careful of it.
While she hissed and rolled, I slid down off the bed, hoping I could put on a condom and get Diana back in the mood, but the moment I touched my cock, I lost control and came against my palm, barely able to catch it all.
Thank goodness for the shirt I'd slept in the previous night. I told Diana I twisted my ankle and, having used that lie quite a lot in high school to get out of… well, lots of things… I was good at faking it.
The sex, though, had been a miserable failure, and it was mostly, if not completely, my fault.
Diana and I dressed in silence and I walked the dog. When I came back, she said she'd gotten a call from work.
"I have to go in Monday," she said. "Do you mind if we change your flight to tomorrow night?"
I had no idea that was even possible, but I said that was fine and she called and took care of it. I called my roommate and told him I was coming back Sunday night, and he said he'd pick me up as we arranged.
I think that helped matters. We were talking again, and we went out to a light dinner and then to see the remastered Episode IV. We were geeks.
After the movie, we talked for a while before going to bed. The conversation, I seem to recall, was mostly facile -- comparisons between the new and the old versions, what might change in the next two films, that sort of thing. We changed into our pajamas with no modesty at all -- I very much appreciated her body even during the mundane actions of dressing and undressing -- and went to bed. There was a chaste kiss, I believe on the lips, but that was it.
I thought the night was over, but I was wrong.
I woke at about two with severe stomach cramps, and climbed carefully over Diana to go to the bathroom -- the only bathroom in the little house she and Kate shared.
Yes. It went exactly as bad as that.
"Hey."
"Huh?" Diana was completely out of it.
"Your bathroom's broke. I need to get something to fix it. Can I have your keys?"
"Dr… esser…"
She was asleep before I had even gotten halfway dressed, and I got the hell out of the house, hoping to pick up what I needed and get back before either Diana or Kate woke up and needed to use the bathroom.
I have always had a good head for directions, and though I accidentally ran several red lights -- in that part of Springfield, the lights were on poles on the corners, instead of hanging over the intersections -- I made it to Jewel/Osco without incident.
It was freezing -- no warmer than twenty degrees -- and I was so concerned with getting into the store that I didn't look where I was going.
Foot on ice.
Me on ass.
Knee on fire.
Oh.
Shit.
It was an extremely mild twist -- I wasn't even limping by the time I paid for the plunger and got back to the car -- but it had scared the hell out of me. My parents didn't know I was in Illinois, and if I'd been taken to the hospital, not only would they have found out I was halfway across the country without their knowledge, but Diana and Kate would know what I had done to their toilet.
Go ahead and laugh. I'll wait.
Done? Good.
It took about an hour to fix the toilet -- the water pressure was extremely low in that house -- and throughout the entire ordeal, Kate's cat watched me from up on the counter as I sat on the floor, waiting for the water to go down or the tank to fill. I climbed into bed about four and passed out.
The ride back to St. Louis was quiet. I stared out the window for most of it. Diana dropped me off at the departure doors for TWA, gave me a hug, and was gone before I was inside the terminal building. I read some books for English Comp II on the flight back, and my roommate and his girlfriend were waiting at the airport, holding up a little handwritten sign with my name on it.
I e-mailed Diana when I got back to the dorm, but I never got a response.
I never saw Diana on AOL again, not under either of her screen names.
I sent her several e-mails, none of which were returned.
I even sent her a Christmas card.
But that hug was the last touch I ever got from Diana, and watching her get into her car… that was the last time I saw her.
That's the whole sordid story. One good evening, one amazing morning, one dismal failure of an afternoon, and one vastly unpleasant overnight. But if I omitted certain details in the telling, I discovered that my fraternity brothers were completely blown away by the story. Until I showed them the flight vouchers and some photos I had taken, not a one of them believed the story.
Now it's a legend. The new brothers, the ones who've been initiated after I left the college, are often told a version of this story, and they're all amazed.
It's nice to have a legacy. Maybe when I set out the official story to the next crop of brothers -- which I'll probably do during Alumni Weekend later this year or early next year -- it might lose some of its luster, but really, how many eighteen-year-olds can say a woman flew them more than one thousand miles just to have sex?
Or, as the brothers call it, "The Legend of Listener's 1,000-mile Booty Call".
Diana, if you're reading this, I'm sorry for what happened that Saturday in 1997, and I'd really like to talk to you, to apologize directly. If I could do it again, you can imagine what I'd change, and I'm sure you can imagine what would stay the same. You were a part of my life that I don't regret for a second -- except for that moment when I hurt you, and what happened early Sunday morning, but I think you can understand that.
And even if you don't reach out to me, know that I think fondly of our time together, and if my choice was losing it all or keeping it exactly as it is, I would choose the latter without hesitation.
*****
7760 words.
Feel free to review. I'll be posting more "Shell Game" in a few days, if I have time, but this story just started pouring out and I had to finish it, to the exclusion of posting more "Shell Game". Like I said, it's a true story, as unflinchingly-accurate as I could make it. I'm sure similar things have happened to at least some of you.
Think of it as a confession. I have confessed. Now back to our usual BDSM-flavored smut.