by Leslie
"You're kidding" I gasped, surprise written over my face. "Aren't you?" I persisted as he gripped the heel with both hands, starring straight ahead as he drove. "Tell me you're kidding, Kenneth" I demanded, the sinking feeling now growing.
Kenneth was 17, a year older than me, and we had been friends for the past two years. We were both in the high school band and met at camp the beginning of my freshman year. We had the same interests in music, girls, etc., and had a pretty normal teenage male relationship. It began that way at least. Somewhere around my 15th birthday things started changing. While Kenneth had always been a bit more outgoing than me he seemed now to grow more dominant in our relationship. When he turned 16 and began driving, he held even more sway over me, he was my means of transportation, and if I wanted to do anything other than go to school, I needed him. He picked me up each morning and brought me home in the afternoons. When I wasn't with Kenneth, I was walking. To a 16 year old, that defines a lot.
So, it shouldn't have been a great surprise that I should find him talking me in to doing whatever it was that he wanted. As it turned out, he figured out long before I did, what he wanted was what I wanted as well.
We had spent the night at each other's house since the beginning of the friendship. Again, natural teenage relationship, guys do that. After the first year, though, things started to change. Oh, it's natural for guys to talk about sex and girls (especially if they've not had either), and I guess a certain amount of good natured horseplay with sexual content is par for the course. And I guess you could say our first encounter was just taking things to a logical conclusion, after months of politely brushing aside his advances, as we were spending the night at my house, I let him go down on me. I could hardly believe that a feeling could be so good, and hoped it would never end. When he begged me to reciprocate, I pretended it was a one time thing, never to be repeated. I made him wear a condom so I wouldn't have to touch or taste his dick. We laughed and joked about it the next day, but the die was cast, and I knew it. Secretly I had enjoyed it too much to think of not doing it again, and my thoughts kept drifting back to it over the next day. He must have too, and within two days we found ourselves spending the night at his house discovering the joys of 69. Within a month we crossed the final imaginary line in the relationship as we both lost our virginity in the only place left. We were lovers now, not just friends, and with hot teenage passion guiding us, we attempted to consummate the relationship in every conceivable spot in the county. His car became our bedroom as well as transportation. We found new and increasingly exciting places for our assignations including the woods, the park, and even the deserted high school gym one weekend night.
Ours was a small town, just three stoplights, but one blessed with location. At the intersection of an east- west and north-south highway we were only an hour to the west of the worlds largest Naval base, and no more than two hours north of a large Army base and an Air Force installation. We were also blessed with a very busy Greyhound bus terminal which stayed open 24 hours each day. It stayed packed with sailors, soldiers, and other travelers through out the day and night. The men's room had four urinals along one wall with seven stalls with doors along the opposite wall. Each stall was wooden and some thoughtful soul had cut glory holes between each. Kenneth had discovered the place, late one night, and suggested I try it sometime. Before I had a chance to, he ran into big trouble there, the result of which led to the conversation we were now having as we drove to school. "Explain it to me again" I demanded "I'm not sure I really understand" "Well" he hesitated "I decided to go to the bus station and see if the rumors about the men's room were true, you know that it was a good place to get a blow job. There were three guys at the urinals, so I went in one of the stalls and sat on the commode. There was a hole cut in the partition between the two stalls. The hole was big enough to put your fist through, and I could see through to the next stall. I had been sitting there about a minute when someone came into the next stall and shut the door. He stood there in front of the commode and pulled out his dick. It was limp, but as he stroked it became hard, probably six or seven inches, I don't know. I couldn't take my eyes off it and as continued to stare, he turned and pointed it right at the hole I was starring through. Hoping he would take the hint, I pressed my opened mouth against the wall at the hole. Sure enough, he pushed the head of his dick through the hole and into my mouth. Just as I was beginning to suck on him the door burst open and two guys grabbed me by the arm and leg and pulled me out of my stall and in to where the guy who's cock I was sucking was standing. I thought they were going to make me suck them all, but instead they grabbed me by the throat and told me they were going to beat the shit out of me, beat me til I couldn't even open my mouth to take another dick in it. I pleaded with them, told them if they let me alone I would do anything they wanted. Well they told me there was nothing I could do that they wanted because they had sex the normal way, with girls. So I blurted out that I could get them a girl for sex. They quieted down and started asking me questions. Well, the only girl I could think of was Cheryl"
"Your sister" I gasped "you told them they could have sex with Cheryl? She's going to kick your ever loving ass"
"I told them Cheryl was a virgin" he went on "and she was going to stay that way until she married. But I told them she took care of her boyfriends in other ways, jerked and sucked them off. Well, that peaked their interest and they told me if I could get Cheryl to take them on that they wouldn't beat me up. So, I said yes, only thing I could think of. I've put them off for two weeks now, they came to town last weekend looking for me, and they've said they're coming back this weekend and if Cheryl's not around they are going to really hurt me."
"So how do I fit into all of this?" I asked, feeling that I already knew the answer.
"You could pass for a girl" Kenneth began.
"Wait" I interrupted "if that's what this is all about, forget it"
"No wait" he pleaded "you could. You're Cheryl's size, your body is as smooth as hers and you 're not hairy like me, yet. Your face would pass, your body would pass, it would work"
"Kenneth, what happens when these guys want to screw?" I asked "when they find the little surprise I have down there, they'll kill us both" Uh-oh, the tone of that sounded like I had agreed to do what he wanted. Sure enough, Kenneth sensed a weakening on my part and pressed on.
"Like I said, I told them Cheryl won't screw. So all you have to do is suck a few dicks"
"How may is a few" I asked, already regretting the question, because again it showed that I was weakening.
"Well, there were three in the men's room, and a fourth came with them last weekend, so I'd say four, yeah, no more than four. Four wouldn't be bad, would it. Hell, I'd like to suck four dicks".
"Under other circumstances, maybe, but I'm not so sure how enjoyable it would be like this"
"Then you'll do it?" It was less of a question than a comment. Kenneth knew he could talk me into most anything, I just had to protest a bit, and he had to convince a bit.
"Only if we can practice this dressing thing first and I'm convinced I can convince someone else" I answered.
"Great" he said "Cheryl is at cheerleading camp til Sunday so we can use her stuff. Why don't we skip school this afternoon, my parents are working, and we can dress you up in her bedroom"
"OK" I replied, as we walked toward the school building "see you here before lunch"
To tell you the truth, I thought about it all morning. Classes passed in a blur as I tried to imagine myself as a girl. True, sex with Kenneth had to it certain feminine elements, but that was both for him and me. And true, at times when I saw other boys in a sexual fantasy with me, I was always the submissive one, the feminine role. So what was different here? The fact that I was going to be trying to fool these boys, that's what. And, the fact that they would kill me if they knew it.
Before I knew it the morning was past us, and we were in Cheryl's very girlie bedroom, surrounded by all her very trendy clothes, her closet full of shoes, and what looked like a department store collection of wigs, all on individual stands. The choice was mine. I stripped and stood naked in the plush carpet, examining my body in the full length mirror. I must admit, except for some fuzz on my legs and arms and budding pubic hair, my body could pass for a girl. Pushing my limp dick between my legs and squeezing them together did give the impression of a young, flat chested girl.
I found a pair of white bikini style panties and a matching low cut snap in front bra in Cheryl's clothes hamper. Apparently she had worn them before leaving for cheerleading camp and the thought of having her scent next to my skin made me feel even more feminine. I pulled the panties up tight around my hips and again tucked my now hardening dick between my legs. I slipped into the bra, snapping it in front, and tightened the straps until my chest was squeezed into an illusion of cleavage passable as a young girls budding breasts. Satisfied with the look so far, I found a pair of taupe nude panty hose in her drawer. Sitting on the edge of the bed, I rolled each onto my feet, first my right then left, and slowly pulled them up my legs. Standing, I hiked them the rest of the way up to my waist. Turning in the mirror, I admired the results of my transformation so far. So did Kenneth, and he let out an appreciative whistle.
Rummaging through the closet, I chose a black mid thigh length skirt and a pink long sleeve sweeter that buttoned in the back. Slipping them on, I chose a pair of black low heels to finish the outfit. Again viewing the results in the mirror pleased me.
"Wow" Kenneth exclaimed "you look great. How about the wig?" I chose a brunette (my hair is brown) shoulder length which fit my head like a glove. Lipstick would complete the look, but I didn't want to bother with that now. Kenneth's parents would be home shortly and I didn't want to take the chance of being caught with red lips.
"Suck me?" Kenneth asked, again not so much a question as a command. As he stood in front of the mirror, I knelt in front of him, unbuckled his pants and unzipped his fly. Pulling his pants and shorts down to his knees, I gazed at his cock head, now directly in front of me. He was gazing down at me as I wrapped my right hand around his meat and pulled the swollen head past my lips and into my waiting mouth. I stopped with the head in my mouth and began to lick the underside of his shaft with my tongue, letting it slip past my lower lip. Playing catch up with my mouth, my lips slowly moved down the length of his dick until the head was against the back of my mouth. Holding back the tendency to gag, I slowly pulled my head back letting his dick emerge from my wet mouth. When just the head was left in, I opened wide and slid forward again, this time letting the head slide past the back of my mouth and into my throat. I held it there for as long as I could hold my breath, then slowly pulled back again this time letting the head come completely out of my mouth, resting on my outstretched tongue. With my mouth still gaped open, I began slowly jacking his cock with my right hand, increasing the tempo as his breathing became more and more labored. I knew he would not last long at this pace. As I continued to jack him he began a slow rocking forward and back, letting his dick slide in and out of my open mouth, my upper teeth scraping over the head. When he could stand it no longer, he shot into my mouth, onto my tongue. I clamped my lips tight around his cock head and began to pull it, spurting warm, delicious cum into my mouth. I sucked hard until my mouth was full to the brim, then pulled back, tilted my head back farther, and swallowed the entire load. It felt wonderful as it slowly slid down my hot throat on it's way to my stomach.
I'm not sure who was more shocked, Kenneth or me. Neither of us had ever had cum in our mouths before, let alone swallowed it. It was a new milestone, I had now jumped ahead of him in experience, but knowing him, he would catch up before long.
I quickly undressed and replaced Cheryl's clothes where I had found them. I was dressed in my clothes and out of the house before Kenneth's parents returned. I was flushed with the excitement of what I had done, and I was paranoid about it as well. On returning to my house I went straight to the bathroom, cleaning up, avoiding contact with anyone as I was sure they would be able to detect the smell of cum on my breath.
I couldn't sleep. My mind was drawn back to the experience in Cheryl's clothes and how natural it all had come to me, sort of like I was destined to do that, like I should grow into that instead of the path to masculinity laid out for me. I wasn't confused about gender, I realized that years later, it was as if I was genderless and could be in whatever mode of dress I wanted anytime I wanted. It was a powerful feeling that kept me awake, I must have my own clothes to wear. But where would I get them? I couldn't take Cheryl's or mom's, they would miss them. And I certainly couldn't buy them.
Finally, it must have been after midnight, it dawned on me that I had seen plenty of clothes, all kinds of them, hanging on clothes lines in the neighborhoods. I thought for sure that some must be left out all night. So, I slipped quietly out of the house and began prowling the backyards. The first night I found a bra, a nice black low cut one that fit me perfectly. I wore that to school the next day, underneath my sweatshirt. Surprisingly, no one detected it and I passed the day in a heavenly daze of arousal and daydreaming. That night, I slipped out earlier so I could cover more territory and was rewarded with a pair of black bikini panties and two pair of panty hose one black one taupe. I passed Wednesday in a state of perpetual bliss and arousal in my panties, bra, and black hose. Still no one detected or suspected that the quite boy sitting in class or walking in the halls was secretly wearing sexy underwear and loving every minute of it.
On the ride home from school I confided in Kenneth. He surprised me with his lack of enthusiasm for my new feelings, given the scene in Cheryl's bedroom on Monday and the fact that I had started this whole thing to help him. "What gives?" I asked after several minutes of silence "I thought you wanted me to get into this". "Yeah, but I didn't expect you to get so into it. I mean wearing girls underwear to school?" he sighed. "Look" I replied "I didn't know I would enjoy it, I just do. And I don't see anything wrong with it. Tell me, what's more feminine that sucking another boy's dick? I just see the two as part of one same thing Kenneth, it's what I want to do, so what's wrong with it?" He didn't answer, I suppose he couldn't answer because he didn't have a rebuttal. After all, what we had been doing was as far from "normal" in our town as anything was. I just wanted to do it as a girl.
By Thursday night, I had collected a red satin long sleeved blouse and a black mini. I actually went out both nights dressed under my clothes and undressed and tried on the blouse and skirt before taking them. It was quite a turn on to be dressed outside, and knowing that I could be caught at any time only added to the excitement. I wore the blouse as a shirt to school Friday. I caught a few inquisitive looks, but no one actually said anything about it.
I began experimenting with Nair Wednesday. I applied it to my legs first, with great results. The light fuzz was completely gone by Friday and my legs, ass, stomach, chest and arms were waxy smooth. I painted my toenails a bright red on Thursday (my fingernails would have to wait until I made the final move in college a few years later) and began plucking and shaping my eyebrows. Since I didn't yet have a beard (or even the hint of one) I didn't really have a lot of work to do.
I had gone through a mental as well as physical transformation that week, and by Friday I found myself in a completely different frame of mind. I couldn't wait for the days to be over so I could venture out a night and dress as my feminine self. I found that I enjoyed that time much more than the time during the day when I existed in male garb, and I knew then that someday I would be free to indulge in either at my discretion. I didn't then realize how true that would become (that's another story).
While I continued to ride to school and back with Kenneth, and we did talk on the phone most nights, we didn't have sex since Monday, a record for us. I don't know if he was frequenting the bus station and he didn't say but four days was an eternity to our teenage passion. During my nocturnal ramblings in panties, I had been masturbating at least twice a night. The tension was building in me, I needed to suck something to relieve it.
On Friday night Kenneth called to say that the sailors had sent word that they would be here on Saturday. I didn't ask how they sent word, but I suspected he had been in the bus station at the glory holes again. My parents were to be at a party Saturday night so we agreed that Kenneth would collect the shoes and wig I had selected from Cheryl's wardrobe and bring them to my house at seven. I had already decided to wear my own panties, bra, hose, skirt and blouse instead of Cheryl's . I could dress and we were to meet the sailors at the bus station. We decided to take them out to the lake, about 5 miles out of town and very secluded at night.
I also told Kenneth that I had decided not to be his sister Cheryl, but to be his sister Leslie.
"Whatever" he sighed "you are really into this girl thing aren't you?". I just smiled. I couldn't sleep til very late Friday night, thoughts of Saturday kept me awake. What would they be like, how many, would they really fall for this, what would they do to me? The line Kenneth was going to feed them was that I was going to stay a virgin til I married, and besides I was having my period now anyway so screwing was out of the question, but I was willing to give them head. Thinking about it brought back memories of the delicious cum I had eaten Monday and I had to masturbate to get to sleep.
The hours passed so slowly Saturday that I thought seven would never come. At six my parents left. I had told them that I was going to spend the night at Kenneth's like I often did on weekend nights. As soon as their car was out of the driveway I flew upstairs and stripped. In minutes I had the panties and bra on and was admiring myself in the mirror. As I became aroused at the sight, my dick became hard and strained against the panties. Panic hit! What if these guys tried to make me strip? Sure, no fucking, but they just might want to take my clothes off . Shit, my dick would give the whole thing away. As convincing as I looked, there was no hiding my hard on, and if I enjoyed the evenings activities like I thought I would, it would stay hard. Searching in mom's bathroom I saw the answer, a box of kotex hidden under the sink. Back in her room I found the belt used to hold them on. With my dick folded back between my legs a kotex pad with the belt pulled up tight kept it all in. Putting the panties back on all I could detect in the mirror was the bulge of the pad between my legs, no sign of my hard on now! Pulling on the black panty hose made things even more believable. The skirt and blouse completed the transformation as far as I could do it without Kenneth. Luckily he was early, and by six forty five I had the wig firmly in place and the 3 inch heels on. I used some of mom's pink lipstick to finish things off. As I stood before the mirror in her room the excitement was unbearable. I was nervous, sure, but as I looked into the mirror what stood there was a girl, a gorgeous girl, a girl any young (or old for that matter) man would love to have sex with.
Being dressed as Leslie gave me renewed confidence in myself and the excitement of the moment completely outweighed any fear I had. It was if I was destined to be her and this moment, no this evening, was destined to be Leslie's birth into the world. I could hardly wait.
Kenneth wasn't sharing my elation, he was scared shitless as he parked the car across the street from the bus station in a church parking lot. "Stay here" he said "I'll go meet them and bring them here" and with that he was out of the car and across the street. Before he could enter the station, three young men in civilian dress with short haircuts came out. One grabbed him by the arm and started to talk to him. I could tell by his gestures and Kenneth's cowering that he was being threatened. Kenneth gestured toward the car and me, and I could see the sailor smile as they all three gazed in my direction. As they crossed the street toward the car some (most) of my self confidence left me and I was again gripped with fear. But something about the adrenaline flow carried me through without fainting right then and there.
"Uh.....guys.....this is my sister.........uh......Leslie" Kenneth stammered as two of the sailors got into the back seat and the third, the one who had grabbed Kenneth in front of the station, opened my door and squeezed in, as I slid across the seat toward Kenneth. "Hi Leslie" the one sitting beside me said as he slid his arm behind me on the seat back. "Hi" I said in the softest voice I could find. Surprisingly it sounded very feminine to my ear, and maybe to theirs as well since no one seemed to catch on to anything strange. Oh well, so far so good, I thought to myself as Kenneth guided the car out of the parking lot. They were all quite on the ride to the lake, I don't know if they were as nervous as Kenneth and I were or if they were just shy. Kenneth guided the car around the edge of the lake and into the woods on the far side. There was a small opening in the trees and brush he drove through and before we had gone another twenty feet we were completely out of sight of the lake or anyone who happened to drive by. He cut the lights and engine. It was completely quiet now, a nervous kind of still.
"Well, I guess you know what we're here for" the guy sitting beside me said, the first words he had spoken since he said hi. "Uh" Kenneth started "Leslie will do you but........."
"Shut up faggot" the guy beside me said "or I'll beat your little cocksucking ass"
"Look" I said "Let's get on with it, you guys are making me nervous with that kind of talk".
"OK, everybody but Leslie and me, out of the car" he said, taking charge "I'm first, you two can fight over seconds". Kenneth and the other two sailors got out of the car and walked back toward the lake. As soon as they were gone, my new friend pulled me close and covered my mouth with his, parting my teeth and forcing his tongue in my mouth. I had never been kissed by a boy before, and I found the experience a turn on. I relaxed my jaw muscles and began sucking on his tongue. I had wrapped my arms around his neck and he ran his hands down my back to my ass, straightening out and pulling my full up against him. We slowly sank back on the front seat, and he came up on top of me. I spread my legs just enough for him to fit down between them, his cock pushing hard against the kotex between my legs, which inturn pressed down on my hardening dick. I kicked my high heels off and brought my knees up on either side of him, pressing what would have been my pussy into him even harder. He began a slow steady thrust into my groin like we were fucking and I rose to meet each stroke. Forgetting myself completely, I began to moan as my hands moved down his back to his buttocks pressing him harder and harder into my dick. I was beside myself, and if I thought he wouldn't kill me for the deception, I would have dropped my panty hose and panties and taken him into my waiting love hole. It was itching for action, deep penetrating action.
But he knew the score, I guess the tale about being a virgin (underage at that) and being on the rag must have popped back into his mind, because he sat up, and after giving my kotex a feel, began fumbling with his fly. I sat up, straightening my hair, and gazed down at his open pants. Instinctively I reached in while he was still unbuckling his belt, and groped for his penis. "Hungry?" he asked once again looking into my flushed face. "Oh yes" I sighed in my best little girl voice, and tightened by grip on his love muscle "very hungry". "Well dive right in Leslie" he invited as his pants finally came undone. I pulled down the front of his briefs and pulled out a very nice, semi hard, cock. I couldn't tell the length, but from the size of the head, I knew it had to be large, larger than Kenneth's and much larger than mine. I slowly, gently jacked it with my right hand as my left slid down to his ball sack and squeezed them. The combination had him hard in no time, and I was delighted to see what had to be at least eight inches of lovely cock. I could wait no longer, and I dropped my face into his lap, my open mouth engulfing the head of his tool, while my fingers worked up and down the shaft like I was jacking him off in my mouth. Meanwhile, the fingers of my left hand continued to work on his large nuts. My tongue slipped between my lower lip and his shaft and I began licking the underside. Then I slipped half of it into my open mouth, clamping tight with my lips and slowly pulling my head up and his dick out of my mouth. When it was nearly all out, I began to slowly re insert it, now taking up to three quarters of it's length in with the head nearly against the back of my throat. Again pulling it nearly all the way out, I dropped on it this time forcing the head past the entrance of my throat. As I held back a gag, my eyes filled with tears. I've since learned that this is a natural reaction, but this was my first experience with true deep throat, and it scared, excited, and enthralled me all at the same time. Now I forced it farther in, until I could feel his pubic hair press against my nose. I hadn't any practice at this, that would come over time, and didn't breathe well through my nose with a dick so far down my throat, so I quickly pulled back until half of it was out of my mouth. I began jacking that half while sucking furiously on the rest. That had the desired results, and soon I felt him stiffen just before the first warm blast of cum shot into my eager mouth. I swallowed fast, but he came faster, and I soon found myself with a mouth about to explode with cum. It was a miracle that I managed to swallow it all without losing any, but I did. I continued to suck and stroke and deep throat as he continued to ooze the delicious, warm, salty load. I had to have it all, I couldn't get enough. He, however had enough, and soon pulled his limp cock from my still sucking mouth. "Wow, you are hungry" he said, stuffing his dick back in his underwear "just hold tight, we've got plenty of this between the three of us" and with that he opened the car door and called for his buddies.
It dawned on me that I had just sucked the second dick of my career. I vowed then to never stop.
There was no kissing or caressing with number two. I guess that's what they mean about sloppy seconds. He opened the car door and had me sit facing him as he stood outside. I spread my legs so he could stand against me and put his half hard dick in my waiting mouth. As I reached around him and grasped his buttocks, he began fucking my mouth furiously. He had about five or six inches, so I had no trouble deep throating him. In no time at all he had shot into my throat and I had no problem swallowing his load without really working at it.
Number three was another story all together. First, he didn't want it in the car he wanted to go into the woods. Kenneth tried to protest, but I was afraid they were going to beat him up, so I agreed to go. We took the blanket from the trunk and went deeper into the woods, away from the lake. He spread the blanket on the ground and laid down on it, pulling his shoes, pants, and underwear off. I knelt between his legs and took his cock into my mouth rather quickly and began to jack and suck him off. "Not so fast" he said, pushing my head up and my lips off his meat "I want to fuck you first". Panic struck me like a ton of bricks falling on me. "Uh, no, that's not the deal" I tried to sound confident, but the fear in my voice let me down. "I'm a virgin, I'm having my period..........." it sounded like a plea. "No problem" he laughed "I don't want to fuck you there, I want to fuck you in the ass" and with that, he grabbed me by the shoulders and pulled me down beside him. I didn't know what to do, I thought about running but figured I couldn't outrun them, and besides, they had Kenneth. I thought that maybe with the combination of kotex and a well placed hand maybe I could keep my balls and dick hidden. No, that wouldn't work, my dick was to hard to hide if he took my panty hose off. I had no idea what to do. If I let him have his way he would surely discover the deception and they might kill both Kenneth and me. If I fought, he just might rape me, finding out anyway. No I was just going to have to let him to it, that was for sure, and I was going to have to keep his attention diverted some way. I had no idea.
When my thoughts snapped back into focus, he was unbuttoning my blouse and pulling it out of my skirt. I moved up to his face and began kissing him, trying to keep his eyes closed. With my other hand I began unbuttoned the side buttons of my skirt and pushed it down and kicked it off with my legs. I lifted my arms as he pulled the blouse off. He began massaging my breasts through the fabric of my bra. I hoped he would think they were too small to bother with. Soon his left hand found my crotch and he massaged the kotex as if he was rubbing my pussy through it. It was so thick that he couldn't feel my dick on the other side, and his constant pressure was forcing it, literally, up in me. I found out later that this was the infamous "tuck" but for now it was just a painful experience and I grimaced with each thrust of his rough hand. He must have thought it was because of the period. By now my dick was softening f rom the intense pressure. As soon as my left hand touched his rigid cock, my pain disappeared and my mind focused on the wonderful thing in my hand as I began to jack him, his tongue probing for the back of my throat. I wondered how excited he would have been if he knew just how much cum had been in it tonight. I know I was terribly turned on.
After what seemed like an eternity, he turned me over on my stomach and pulled my panty hose down to my knees. Reaching under my waist, he helped me to my hands and knees and started to pull my panties down from the back. I moved my hand to the front and slipped it over the elastic and until it was covering the kotex. From the impromptu "tuck" he had given me everything seemed to be in place and it didn't take much of my hand to cover it all. Thankfully he didn't pull my panties any lower than necessary to get at my ass crack, and apparently he wasn't anxious to get blood on himself so he didn't full around in the area that would have been my pussy. He moved around in front of me and put his dick in my mouth. "Wet it" he commanded and I hungrily sucked and slurped and slobbered til it was coated in a thick film of my saliva. "Take it easy" he warned "I'll save some for you" and he pulled out and came round behind me again.
I could feel him spreading my ass cheeks with both hands and then before I knew it, his thick cock head was pressed up against the pucker of my hairless hole. I groaned as the pressure increased, and gasped as I felt the entrance to my feminine being slowly yield and open to the tip of his member. Slowly, but with constant pressure behind it, his cock head struggled to overcome the resistance, and with on final jab that made me cry out, it was inside. He stopped, waiting for me to adjust the intrusion, and after a few seconds of pain, I felt the muscles relaxing. He sensed this too, and I could feel his cock slipping further in. He stopped again to let me get used to it and after I relaxed again, he pulled out slightly, then pushed even further in. By now the pain had dulled and was replaced with sensitivity as I could feel every movement of him inside me. It was heavenly and I knew then and there what I was made for. I was made to give pleasure to men and get an immense amount of it in return. I was turned that night, completely turned and I've never gone back, I've never abandoned my role. I don't know his name, I never saw him after that night, but where ever he is (and if by some improbable chance he's reading this) he turned a shy, confused, 16 year old boy into a woman. And I, as well as the hundreds of men I've been with, thank you sailor.
He continued to thrust in until his balls were resting against my panties. The feeling was pure rapture and I could feel my dick gone completely limp under the kotex pad. He began a steady fuck, and I pressed my ass back to meet each thrust. "I'm going to cum" he announced in a raspy voice "do you want it in your ass or your mouth?" As much as I wanted to taste his cum in my mouth and feel it slide down my throat, I was so on fire inside that I knew I had no choice. "In my ass" I moaned. While Kenneth and I had fucked each other, neither had cum inside.
With increasing tempo he slammed into my now undulating ass cheeks. He tightened his grip on my hips, thrust in all the way, and I could feel the first spurts of hot creamy cum empty in my stretched love channel. Spurt followed spurt and soon I could feel my insides filling with the delicious fluid. "And your mouth" he said as he pulled out of my love hole and repositioned himself in front of me, his dick covered with cum and my sex. I eagerly took it in my mouth, my tongue lapping and licking and my mouth sucking for every drop of cum left in it. He squeezed his ballsack and jacked his shaft to help me in my task. The mixture of my ass and his cum had an overwhelming influence on me, and in later life I would come to realize that there was no better taste. When he pulled his now clean, dry dick from my lips, I lay down on the blanket, exhausted. We dressed hurriedly, collected the blanket and began to walk back toward the car. "You were great, Leslie" he said. "Thank you" I replied, the taste of cum still on my tongue.
As we approached the car I saw Kenneth standing on one side and the two sailors on the other. They made no move toward getting in the car, which lead me to believe that the night's activities weren't yet over. That was fine with me, I was still on fire with desire, I wanted it to last longer.
"Say Leslie" one of them said to me "you're really good. Have you ever got it on with your faggot brother here?"
"Uh, no......he won't let me" I stammered, not really knowing what to say to a question like that. I figured if I told them that Kenneth wouldn't let me maybe they would leave him alone.
"Well, well, Kenneth my boy, you don't know what you're missing. Surely you would let your sister suck your dick, I mean after all she is good" he said as he looked menacingly at Kenneth.
"Uh, well........I guess" Kenneth said, not entirely convincing in my mind, as he came around to where we were standing.
"Get him Leslie" the sailor said as spread the blanket at my feet "we'll watch". With that, I sank to my knees on the blanket and unzipped Kenneth's fly as he unbuckled his belt and unbuttoned his pants. I pulled both his pants and his underwear down to his ankles. His dick was soft, I guess he was scared, and I started by holding it to the side as I licked and then took his balls in my mouth and sucked on them. I slowly jacked his dick as it began to harden. Switching my attention, I began to slowly lick his hardening shaft from the underneath all the while keeping my eyes gazing up at his face. He was looking down at me and his eyes were glazed over with desire. I licked up the shaft to the head and flicked my tongue all around it before finally taking it into my open mouth. I softly curled my lips around it and began slowly pulling it into my sucking mouth. I had it all the way in before it was completely hard, and as I held it there, I could feel the head forcing itself past the entrance to my throat. My face was buried in Kenneth's pubic hair, and his balls were against my chin. I continued to suck without moving and Kenneth's cum exploded in my throat, gagging me. I couldn't breathe, and I quickly pulled his dick, still spewing hot cum back until the head was in my mouth. I tried to swallow, but there was too much cum lodged in my throat and I had to open my lips and let it escape around his shaft and onto my chin. It drooled out, a mixture of cum and saliva, and strung down my chin til it became too much and dropped to the blanket. As I moved my knees, I could feel the sticky wetness through my hose. Kenneth slowly pulled his dick from my cream filled mouth, cum stringing from the cockhead to my teeth, tongue and lips.
"Goddamn" said one of the sailors as he guided my right hand to his rigid cock "that's one hell of a blow job" and he moved closer so his dick was near my mouth. Another dick appeared in my left hand, and the third pressed into my still foaming mouth. He would only let me suck the head in while he jacked the length with his hand. With his cockhead on my outstretched tongue, he jacked off into my open mouth, depositing a huge load of delicious, creamy cum. After I had swallowed, I pulled the cocks in my hands to my lips and began to jack them furiously. First one, then the other shot gobs of hot cum in my mouth. It ran out my lips, down my chin and all over my blouse as I worked to swallow all I could. I then finished by licking and sucking each of the three cocks until they were completely cum free.
The ride back to the bus station was another blur for me. I was so moved by the experience that I couldn't focus on anything else. The sailors kept praising my performance and vowed to return again soon. They also invited me to come down to the Naval base for more action. As they left, they kissed me on the cheek.
Kenneth and I were so hot from the experience that we drove back to the lake and made love again. Finally I achieved my first orgasm of the night in Kenneth's mouth, and we lay in each others arms for what seemed like an eternity.
Leslie was born that night. There would be many others, but that's another story!