This is my second story here. Hope you all enjoy!
Note: the names have been changed to protect the gleefully guilty!
It was very early in the afternoon of the day after that most momentous day, the one and only day that Sara and I ever 'fooled around,' that I came to the conclusion that the little seventeen-year-old hussy had seduced me. I remember it quite well, even though it was almost ten years ago. I was lying in my narrow bed in my rat-hole apartment, naked, and contemplating my disaster of a summer, when the realization hit me.
The summer truly was, by all accounts, a disaster. Midway through spring semester, a representative from some student outreach office came to speak to our accounting class about internships for the coming summer. I was interested, signed up, and let, as the representative promised, 'the office do the rest of the work.' What a mistake that was. I foolishly accepted the first offer that came my way, a position at a resort nearly five hours from the University. I was told I would lean the 'ins and outs' of managing a high-class restaurant in a high-class resort, the kind of stuff future employers would drool over when listed on one's resume.
The reality was depressing. Sure, the resort was pretty posh, and the eating establishment it boasted certainly had aspirations to be first-class. It was run by a pompous, Paris-trained chef named Marc. The problem was my job. It was in no manner the career-building experience as advertised. I never really had a chance to learn much of the restaurant trade, save for a few one-on-one talks with Marc about little more than his great accomplishments in the culinary world. Occasionally the general manager of the place, Jim, would 'let' me help him with inventory and ordering. Instead, I was first shoved into the role of a busser of tables, with every now and then running drink orders back to thirsty diners when it got busy. Eventually, two weeks in, Jim realized I was 'one of those smart kids, who could remember stuff' and moved up to a full time server in the bar, rotating a shift in the main dining room, every other weekend It was hard work, we were continually understaffed, the customers were very demanding.
To further my misery, the resort was situated smack-dab in the center of nowhere, Indiana. Sure, it had a fancy view, perched on a bluff overlooking a river. But it was entirely surrounded by hick farms. The only town, if you can call it even that much, was two miles away. The internship office arranged for an apartment for me, really only a half of a lower level of a small country farmhouse, with crazy, drugged out hippie-types for neighbors, and a bewitched, crabby old woman for a landlady, who lived upstairs and called me at least twice a week to tell me my 'freaking teevee' was too loud. I should have been glad that the house was in the town, except that it really wasn't much of a town at all, one stop sign, one gas station, two bars, a grocery store, and about six hundred residents. The next nearest town was a good forty-five minute drive, and it wasn't much of a locale either, its singular highlight being a superstore.
Suffice to say, I was lonely.
That spring semester, I had broken up with my girlfriend, Alice, and we had a rocky four months until we went our separate ways in June, she to her parents in Chicago, me to this crappy internship. Post-breakup had been traumatic for both of us, as we sort of did, what I called, 'a lot of quasi-dating.' It was a rough time for both of us, and often it still felt like we were still dating. But through it all, and into the summer, Alice insisted we were 'only friends.'
The being friends part I could handle. As there really was no internet available (remember, this is quite a while ago), the only communication we had was via phone, and we talked on the phone once or twice a week. She told me about all the guys she was seeing, the adventures she had with them, her exploits in the nightclubs, and how she was more and more interested in trying something with another woman. Despite our vows of non-involvement with each other, we would still have phone sex. I would jack off while she told me of her outings, cumming all over my chest as she described giving a blowjob to a guy in the back seat of a cab, or some such tale. She would masturbate too, hearing my quickened breathing and final moans as I reached orgasm. She often expressed her desire that I find someone, if only to get her off the hook for all the hot encounters she was having.
The only people my own age, or at least close to my own age, worked with me at the resort. And that was where I ran into trouble. In truth, the only guy near my own age of 19 was Jim, and he was 32, and he had no interests save, as best I can describe it, a bizarre obsession with the entire state of Kentucky. There were four women, however.
Carrie and Candice were twin sisters, nearly impossible to tell apart except that Carrie had gotten knocked up four months before I started and I simply remembered her as the one with 'the belly.' She lived with her boyfriend in town and spent most of her spare time with him, or her sister. I didn't care for Candice that much anyway, she had the worst mood swings, resentful of nearly everyone for half a day, and then trying to be sweetly romantic for the rest, scheming of ways to set up co-workers with other co-workers. Her typical mode seemed to be, at least to me, set on 'bitchy,' so I avoided her as much as I could.
Then there was Coles, another busser. Her real name was Nichole, but everyone just shortened it and called her Coles. She was a year younger than me, but still in High School. Or at least, going back to high school for her senior year when that summer was over. Coles was a dancer, and looked it. As tall as me, she had a very slim, lithe body, thin muscular arms, no breasts, no ass, and when she was wearing tight jeans instead of her usual standard work pants, very long muscular legs. She had long, straight, silky red hair, always wrapped in a tight bun while she worked, but she let it hang down past her shoulders when she was off work. She was also contemplating going to the same University as me the next year, and that opened the door for many more conversations we had. Candice noticed this, and, through clumsy manipulations, tried to set us up. We both resisted her attempts, but at last gave in and I asked her out for a dinner. We went out the next weekend, and while eating she told me she really didn't want to date me. She wasn't looking for a long-term relationship and she knew I'd be gone by September. I told her I understood, and that it was fine with me. Eventually I broke down and told her a little about Alice and I, and she was very sympathetic as I told her many of the details.
That left Sara. Sara was a certainly a looker. She was in truth quite short, maybe 5' 2', but she had wonderful eyes, and large mouth with very cute dimples as she gave a gorgeous smile, and long, light-brown hair that was in tiny, tight curls. She was a hostess, and that position did not require her to wear the regulation uniform, and as such, she dressed formal, but often at times very risqué. I didn't mind, but on more than one occasion Marc sent her home to change. But her outfits often included low-cut blouses that advertised her large and fabulous breasts. Now, I'm not much of a breast man myself, I rather prefer them on the smaller side, but hers, in proportion to her smaller frame, quite a handful, proudly perched high on her teenage chest. More than once I caught myself staring down her shirt, as she would reach over sometimes to help set a table, marvelling at the long expanse of those boobs, postulating where the nipples might be, trying to ascertain the exact outline of those perfect mounds. On top of that, often, or at least when she got away with it, she would wear very short skirts, and I can't say her legs were anywhere as thin and long as Coles', but they were shapely and very womanly, and I also like to follow the line of her legs from behind, going from her high-heels clad feet, above her ankle, over her smooth calves, behind her knee, up the back of the leg, almost to that magical crease where her ass cheek met her thigh, but tragically covered by that abominable skirt. Did I sprout a hard-on from this gazing? Oh yes, but I certainly couldn't be the only one, and I always justified it as necessary to my survival that summer in that hell-hole, else I be tempted to hang myself.
There was one problem. This sexy woman was seventeen. Granted, I was nineteen, and would turn twenty soon, and she was a senior, just like Coles, but somehow, to me, that seemed a gulf just too far to even attempt.
She was often object of my furtive nightly stroking. I can't count how many times I stroked my dick to the image of her in whatever she wore that night. I would imagine her in it, slowly stripping for me. By the middle of the summer these imaginings neatly supplanted my frequent phone calls with Alice. She still called, and related her hot adventures to me, so I wound up getting off almost twice a day by then.
Oh, and there was one other problem.
She had a boyfriend! Candice's handiwork had resulted in Sara hooking up with Jim's younger brother (who was 25, and therefore shot my whole I'm-too-old-for-her excuse out the window) the previous February. I was told they were a very happy and committed couple, much to my devastation.
Two weeks before my time sentenced to this awful resort was up, a miracle happened. Sara came to work in tears, and it soon got out among all the staff that her boyfriend had dumped her. I found out early in my shift but we quickly became so swamped that I didn't get a chance to speak to her until later that night.
It was a strange night for the restaurant though, and as fast as the rush came, we had no more new customers after about six. By seven in the evening, there remained only two tables with customers, and Jim had cut most of the servers, save Carrie and myself. Then he left, taking off early for the night. I had no more customers in the bar by eight, so I strolled over to the hostess' station to have a chat with Sara.
She was dressed impeccably again tonight, in a bright pin halter top, a black sweater coat, strategically buttoned only as high enough to leave the immense valley between her breasts visible, and a knee-length black skirt, overall a quite modest get-up for her.
'Hey, Sara, I'm really sorry to hear about you and your boyfriend.' I told her.
'Oh, thanks...I'm okay, really...' she looked in fact like she was going to cry.
I quickly changed the topic and made small talk with her, talking about mundane everyday things, and we chatted on this for a good ten minutes.
'Look, again...It really sucks with your boyfriend and all....that's really too bad.'
To comfort her, I told her a little about Alice and I, and our crazy up and down relationship. Sara seemed lifted by this, and looked a little happier. She asked me some questions about us, laughed at some funny stories. Marc came out of the kitchen after we had talked for half an hour, with a new task for me. I went at it for the next hour, and then found myself stuck with a fair amount of side work, which I worked at, trying to complete as quickly as I could. By ten, there were only three patrons seated at the bar. Normally I would have checked with either Jim or Marc if I could go, but I went into the dining room to talk to Sara again. The lights had been dimmed significantly, and she and another busser were busy vacuuming. I grabbed another vacuum from the supply closet and helped them out. Marc came out, and we all shut off our vacuums to talk to him. He asked Sara what side work was left to do, and told the busser to clock out and go home. He said I could stay and help her finish, but then I better get my ass out of there. We nodded, and went back to work.
Our work was done less than twenty minutes later. I clocked out, and was about to head to the break room to get my things, when she stopped to ask me a favor. She wanted me to wait for her while she changed and collected her things, and walk with her to her car. A few weeks back, the resort manager had decided that all of Marc's staff was parking too close to the resort, and there weren't enough spaces near the main entrance for the customers to park. We had been ordered to park further down by the Cliff Houses, a series of large condos people could rent, about a half mile walk from the restaurant. We all complained and grumbled about it, but we all parked there eventually. Sara felt unsafe walking by herself in the dark to her car, so I agreed.
Ten minutes later, we met back by the hostess' station. But instead of leaving right way, we started talking again, leaning against the counter. I can't quite explain what transpired next. Maybe it was the near-darkness of the dining room. Or the naughtiness, that ensued, occasionally stealing chocolates for each other from under the counter, first me one for her after she dared me to, then she scooped up a whole handful and passed them to me, and we ate them one-by-one. Maybe it was just the relief of being done with work for the evening, freed from a stressful job and respite until five the next afternoon. Whatever it was, it was magic. As we got to talking, our inhibitions were lowered, and the talk became explicit.
It started not too long after we talked about Alice and I again. I hadn't quite reached the stage of total disclosure, and I later realized that she was trying to determine if we had phone sex. I was a little hesitant to admit, even at that point, that I, in fact, masturbated.
'Well, do you ever get off, you know, when she talks to you?' she insisted.
'From just her talking...or do ya touch yerself?'
'Sometimes...I kinda do touch...myself. Yeah.'
'Wow. Oh, that's so hot.'
And then she went on to explain to me how her recent ex had been the 'first guy I had phone sex with!' I was floored.
'Really?' I asked.
'Did you guys have regular sex?' I asked.
'Well, yeah, silly, of course we did!'
'Oh.' I truth, I was really surprised she was sexually active at all. I guess thinking that she was seventeen; perhaps she was still virginal and all. That she was not was really a revelation to me. Then she uttered the words that opened the floodgates for me:
'I bet you I've had sex with more people than you have!'
'No way,' I responded.
'C'mon, how many?'
That was easy. I had only lost my virginity a year and a half prior. 'Four.' I told her.
She smiled. 'Fifteen.'
Fifteen?! Holy Crap! I started questioning her about it, and we then launched into what was essentially a cataloguing of every sexual partner we've had and the various sexual acts committed with them. She had me way beat.
'Once, with Alice.' I responded. 'You?'
'Yeah, just once, with Erik.'
'Ever had sex under a ceiling mirror?'
'Um...no.' I never thought of that. The possibilities tumbled through my head. Then I pictured Sara in the act, on her back, looking up and seeing the reflection of her partners backside thrusting into her. 'Have you?' I asked.
'Yeah, twice, once with Greg and once with Brad.'
And so we went on, and she was topping me in everything. I was getting discouraged. And hugely turned on. My dick was hard in my pants, and I was thankful for the dim lighting or she would have noticed the bulge, I thought. She asked me about threesomes. I hadn't done that. She had, with a boyfriend and a best friend. Outside? Ha, do you think just horses and cows get it on in the farmer's fields-hell no!
Finally, I had to ask. I was planning on doing it that night anyway, so-
'Sara, do you masturbate?'
Even saying those words got me going. My mouth felt dry, my heart was going a thousand beats a minute.
She actually looked a little sheepish, 'Well sure, I mean, I do need a release from time to time, and a boyfriend isn't always around.'
'Or a best friend,' I joked. She laughed.
'You do, don't you-and not just when you're having phone sex.'
'Nope. I mean...yeah, I masturbate. All the time, in fact.'
'How often do you do it,' I shot back.
'Oh no, I asked you first, you have to tell me!'
Giving in, 'probably every day.'
'Wow. I probably do it once or twice a week.'
'You have no idea how hot that is.' I told her.
'I've always wanted to see a woman masturbate, but never got the chance 'till I went to College.'
Then she asked me a series of questions regarding sex in college. By now it was nearly midnight. At long last, she hinted that the bar was closing soon, and we should get going. We started walking to our cars. We kept up our talk, and then she asked me:
'So, are you going to masturbate when you get home tonight?'
'Oh yeah, big time. I've got a hard on in my pants right now that's so big-!' I shut up. I couldn't believe I just told her that.
Her reaction was a little-girl giggle, and a, 'That's so cute!'
'And you, are you going to get yourself off when you get home?
'Of course. My panties are so wet right now!'
Holy crap! As she said the words 'panties,' I pictured her panties. They were probably thongs, red, nearly hidden, nestled between her ass cheeks, the portion of them over her hairy pussy soaked through and pinkly transparent with her juices. I nearly ejaculated right there in my pants. I told her so. I was really getting bold. We were nearing our cars now.
'Wow,' she said to me, 'someone really needs a release.' She smiled at me.
'I really do!'
'Well, here's my car. Have fun tonight, Darren.'
'Wait-wait...do you wanna do something, maybe, like...'
She shook her head. 'No, it's late.'
'Yeah, but it doesn't have to be for that long-'
'No. no. I can't...it wouldn't be right...it's only been a couple days since the breakup...'
'Please?' I pleaded.
'No, I'm sorry...you're a really sweet guy, you really are, but no.' She unlocked her car and started to get in.
'Okay...bye. Good night, Sara!'
'Good night, Darren.' A wave, another little giggle, and she drove away.
When I couldn't see her headlights anymore, I looked around. It was pitch black, the only illumination from a floodlight in front of a Cliff House at least five hundred feet away. Leaning against my car, I took one more glance around, then unzipped my jeans and pulled my dick out.
The cool air and my engorged tool set tingles coursing through me.
With my left hand, I lightly tickled the underside of my dick, feeling that throbbing vein that courses its whole length. Not able to wait any longer, I fully gripped my dick at the head, and slid it down slowly to the base.
Wow! I was already there!
My hand slid the length back up to the tip of my dick, and twisted my palm over the most-sensitive inflated head, made a full grip again, and ran my hand all the way back down and then-
'AAAAaaahhhhhh!' I moaned out into the night. Wow, had I really been that loud?
'Uhhhh.' Again, another convulsion of orgasm. My eyes were closed, it was so strong, but had they been open I'm sure I would have seen my cum squirting out five feet in front of me on the gravel parking lot.
'Uhhhh.' A glorious third eruption. My hand was still at the base of my dick, in its firm grip. Slowly the pulses of orgasm subsided.
'Uhh. Uhh. Uhh. Uhh.' Usually I was not so vocal. I looked down. My dick was still hard, and the semen was still coming out, drip-drip-dripping over my hand, under my finger, and then finally to the ground. Against the dark gravel surface, with the floodlight the only illumination, my cum virtually glowed in a line. from directly under me, traveling at least seven feet out, it looked like an ill-painted dashed road-line, delineating the course of my pleasure. I shook my enlarged member, stuffed it back in my pants and drove home.
I was hard all the way back.
I got home, ran into my apartment, stripped, and laid on the bed. I jacked off once more, with the image in my mind of Sara doing the exact same to her luscious body, and again a furious amount of semen was emitted from me. I fell asleep right away, but woke several times in the night, and jacked off again each time.
I woke up late the following morning. Unshaved, my sheets askew, dried semen all over my chest and stomach and legs and bedding, I replayed the entire previous evening in my head, felt my dick get hard one last time. Another masturbation session, and I cried out, 'Sara...uhhh, Sara....uhhh. Ohhh!' As I achieved yet another orgasm, my sixth or seventh in the past twenty-four hours. That had to be a personal record!
The next day, Sara did not work, and the day after that, I had off.
I called Alice that night, and related the entire conversation to her, word for word. I also told her about my actions afterwards, and the massive amounts of cum I'd been milking out of me the past few days.
'Wow, that's really great, Darren.' She said, much to my surprise. 'I'm really happy for you. That's so sexy, too! This is great!'
'So...you're okay with this?'
'Yes, of course!'
'And if she and I decide to do something-'
'Go for it, dear! I want you to have fun with her! Lord knows I've been sexin' it up all over Chicago these past few months. No, have at her!'
'Okay then.' I said, much relieved.
'Yeah...hey, hold on a sec...let me find my vibrator, and then I want you to tell me the whole story again...'
Could anyone ask for a better ex?
Sara and I finally had a shift together the next day, but it was extremely busy. The resort was full, and it seemed as if every guest wanted to eat at our restaurant. It wasn't before 11:30 that Jim began to cut staff. I asked to stay on to close.
'Well, it's Candice's night, but see if she'll trade with ya, and if she says yes, then it's fine with me.'
I saw Sara, but we never really got a chance to talk. We exchanged smiles, and winks, but nothing more. We both knew all our co-workers were renowned gossips, and certainly didn't want to give them any more fodder.
Thus, at two in the morning, finally done, by quick agreement, I promised to walk with Sara to her car again. A very long night for both of us, we trudged out there, and I finally spoke:
'Look, about the other night, I'm sorry for being so insistent...it's just, since...Alice and I broke up, and...welll-'
'It's okay, silly. I understand.' We got to our cars. I started to unlock mine, and turned to say goodnight, but she started first.
'Why don't you come in my car for a sec...let's just talk some more.'
I obliged and sat in the passenger seat.
She got in the drivers seat, started her car, and shut the door. I then pulled mine shut. She turned on the radio, found some alt-country station, turned it down a little, and then looked up at me.
'You know what?' She asked, 'It's my fault....I'm the one that got you all riled up. Don't worry about it anymore, ok?'
'Actually, I thought about it last night,' She stopped to giggle. 'As I was playing with myself.' More laughing on her part, and mine. 'And I realized-I kinda let you down hard...so I want to make it up to you. So guess what!'
'What?' I asked.
She had a huge grin now. 'I'm not wearing any underwear!'
'Nope, none! Really! And I'm going to show you!'
'What??!!!' I exclaimed.
She manoeuvred her body sideways, so she was facing me, and swung her right leg up over the center, her foot passing over my head, and rested her leg behind my seat. She then pulled her left knee up, and rested it on the steering wheel. She was wearing a frilly white skirt, with lots of lace and girly fabric accents. She quickly lifted it up, pulling the hem to her chest, and then, just as fast, moved it back down, pressing it in around her crotch.
'Did'ja see my cootie?' she asked. I shook my head. She had gone too fast. She repeated the motion, only slightly slower, and now that I knew to watch carefully, I got a glimpse of pure exposed flesh, but not enough to make out the parts. When asked if I saw it this time, I responded with, 'barely.'
'Ohhh.' She made a mock saddening face. And then repeated it a third time. This time I could clearly make out her pussy, and that she had shaved any hint of hair completely off.
To her inquiry this time: 'A little bit more, I guess.'
She laughed, and flashed me again, once more just a bit slower than before.
'Yup, you're female.' I joked. As we played this game, I began to rise in my pants.
Finally, she pulled it all the way up, and held it in place.
Her pussy was wonderful. It had that soft, inviting look, with her inner vaginal lips protruding out beyond her outer lips. She was clearly as turned on as I was, there was the glistening look of her wetness, and I could smell the distinct aroma of an aroused pussy. She held onto her skirt with one hand, and dropped the other one down, prying her lips apart to show me the treasures beneath.
'God, I'm moist.' She observed.
'Yeah, I'm pretty hard myself.'
'Take it out. I wanna see it!'
'Okay.' My dick was so hard and so rigid, I had trouble getting it out between the fly of my underwear. Finally, I unbuckled my belt and slid my pants down to my knees. My hard-on spring up, touching the bottom five inches of my tee-shirt.
'Wow, you are hard!' she exclaimed.
'Yeah,' I said, returning my gaze to her crotch.
We must have sat there for nearly two minutes looking at each other's parts. Commenting and gasping and, in my case, drooling over.
'I would love to stick it in that hot pussy!' I told her. Lame, but we couldn't exactly be poets in picking out our words, we were so heady with lust.
'Ohhhh, that would be nice!' she said.
'Ok, I'm sorry, I can't take it anymore, I've got to stroke it!' I broke down.
'Really...oh, let me watch!'
'Huh, that's okay with you?'
'Yeah, yeah, that's so hot, do it!'
'Okay, here I go,' I told her, as if she needed narration.
It was wonderful. Slowly going up and down, I could again feel myself so close to that exquisite moment, and the action of my hands was merely to revel in it and show off. My audience was captivated, her mouth agape, her eyes wide. I looked back down at that beautiful pussy. Her hand had returned, and one finger was absently poking around. The sight of her touching herself only heightened me in my aroused state, and I struggled to keep my stroking slow and steady. I could hear myself breathing louder.
'Oh, god, Darren, cum for me!'
I wanted to respond, but couldn't. I kept going back and forth from looking at her face, twisted in pleasure, to her pussy. Her eyes became small slits, focused on my dick. Her finger was now making small circles around the top of her lips, what I assume was her clit.
Neither of us lasted long. 'Okay okay okay okay, I'm gonna, I'm gonna, I'm so close-' I told her.
She had been making little grunts of, 'Yesss...yes...yes...yes...' and her finger was moving so fast it was a blur. I found myself at that familiar point, the moment of inevitability, when I know I'm gonna come, I'm just waiting for that final tingling contraction. I slowed my stroking, and then stopped, holding my hand at the base, right where I like it.
I ejaculated, a nice big glob floating its way up, spreading itself across the underside of the roof of her car. A second load, rising a foot above my dick, and falling back to hearth on my leg. A third. A forth. The fifth merely seeped out.
Sara heard me moan as I orgasm. I watched her eyes, they shot open, just in time to see the second spurt, and the subsequent. When I was done, she looked up.
She then threw her head back. He grunts became the cute, sexy little whimpers. Her hand still strummed across her pussy in blurry motion, and then-
She froze. A second. Another second. And then she emitted huge breaths, with gasps on the inhales.
We both sat and recovered for several minutes.
'Wow, that was...amazing.' I said.
Endnote: That was as far as it ever went between the two of us. Once we settled down, and fixed our clothes proper again, we had a very serious conversation. A real relationship was out of the question, as we really had nothing else in common save our appetites for sex. She was concerned that it went too far, but said in the end she had 'no regrets, though.' And I believe her. We did talk explicitly a few more times at work, leading me to jack off right after work, but we never did it in front of each other again. I left two weeks later, back to school and my ever-complicated relationship with Alice.