Sweet Sixteen
Chapter 1

Copyright© 2017 by Bobspanks

Erotica Sex Story: Chapter 1 - A sixteen year old sissy and total slut gets a birthday wish to die for. After a small gang bang; a few years previous and, overcoming his boyfriends aversion to multiple partners, this becomes a great birthday wish come true!

Caution: This Erotica Sex Story contains strong sexual content, including Teenagers   Consensual   Romantic   Gay   BiSexual   TransGender   Fiction   Gang Bang   Interracial   Black Male   White Male   Anal Sex   Exhibitionism   Oral Sex  

This is a chapter from my novel [something like ‘Call Me Madam’] but from the perspective of a male slut and part time whore. I will post more as time goes on and ... let the reader separate fact from fiction.

It begins in the 1950’s when being gay was tantamount to being a leper in our society. The primary character is not only young – in the beginning – but develops into a full-blown sissy over time. By the time of this chapter he’s had a boyfriend for almost five years, multiple partners and is really enjoying sex. Bobbie has become a full blown male slut...

By the time I was approaching my sixteenth birthday, I’d suffered through the last hard paddling by my father, to break me of being a boislut. He’d just about given up when that didn’t change anything. I’d been punished quite a bit; all it did was turn my backside black and blue (sometimes) and make walking and sitting very uncomfortable for a day or two. I guess I figured that anything that bad, (getting my ass beat regularly for) had to be good. It was; I completely enjoyed sex with guys.

My boyfriend had his driver’s license and a rebuilt Jeep to go along with it. The Jeep made dating better than ever for us. There were a lot of vacant fields, wooded areas and a wealth of places to go parking and have sex. The back seat had been broken in on the first day the Jeep was running. After that, we added some blankets and a few old towels to a box under the back seat.

As summer approached and, my sixteenth birthday, Ron started to ask about what I wanted to do ‘after’ the family birthday party. By then he was okay with me slutting around a little, I’d been having some sex outside of our relationship and loving it. Ron didn’t mind an extra person or two on a camping trip; he was beginning to enjoy watching me getting well fucked by someone else. He was also good about our black friend seeding me whenever he had a chance ... that, he did like to watch. Ron was my lover; everyone else was just someone to fuck me. Bill was a close second. I’d learned to love that black cock and enjoyed being with him; Bill had come a long way – in the love/sex department – since my first time with him. At the age of sixteen I also had the beginnings of my first dirty little secret desire. I had begun to feel that I would love to get pregnant. And, if it had been possible, have Bill be the one to knock me up. I wasn’t much different than all other white bitches. This was one thing that I never talked to Ron about ... ever. Having his baby, yes, having one with Bill, no.

One nice warm night, after at least an hour of very good foreplay and sex, while lying on the blankets in his arms, I told him, “If it can be done ... if you don’t mind ... I’d love to ‘dress’ and have a birthday gang bang.” We talked about it for a while. I could come up with the clothes (with just a little shopping), he thought he could cum up with at least five or six guys that would want to take turns on me. We made a little list; he thought of a few more, in the end it was up to eight, maybe ten. I was going to be one sore little cunt if it worked out.

Since my first little one, at the age of thirteen, there had been some casual ones that revolved around camping. Usually one to three friends, that went with us and, liked fucking me very much. Ron would usually start things off and do me first. The others would watch and take turns as they could. In the end I’d go to sleep loaded with cum, in both ends. The mornings were nice; I’d get to handle everyone’s morning wood – which was always a great way to start the day off.

Once I bought the dress, a nice one that was well above my knees, I ‘borrowed’ one of my sister’s bras and two pair of her panties. She had graduated to some nice briefs which fit me pretty well and, with her smaller breasts, I only needed a little padding to fill out the cups a little. I looked like a plain girl of about fourteen or fifteen when I tried everything on. My hair was shorter but, if I brushed it the right way, I looked like a little butch bitch. No one would be interested in that end of me – after the first few minutes – other than my mouth to stuff with cock.

I took everything along one night, to get Ron’s approval. He loved the outfit.

And, now that he was driving, we had the perfect place. His uncle (who he lived with) had a hunting camp, in the woods, about forty or fifty miles north. It was a comfortable place but very remote; we’d have total privacy.

As the date of my birthday approached, our list had grown to twelve. It was possible that everyone wouldn’t show up but, enough to make me a little nervous. That nervous anticipation of really getting my brains fucked out. It was summer, my birthday party was set-up for a Saturday. We were going to have a bonfire after the party then, Ron and I were going to leave for the camp. Everyone else had maps and could follow as they wished. We had a request to join us, from another friend and, he asked if he could bring someone along. That made it fourteen; if everyone showed up I was going to be one sore little cunt!

I did take some other clothes along; an older flannel nightgown of my sisters, some short shorts and a few shirts and t-shirts for lounging. I didn’t think I’d spend much time with my clothes on and, wanted to make it as easy as possible.

On the trip up I gave Ron a nice sloppy blow job. We hadn’t had sex in about a week and, I wanted him to give me a good long fucking when we arrived. Taking his first big delicious load was a pleasure and assured that. I then took some time to get dressed – I wanted to arrive ready and with just a little makeup. I was nervous, I was horny and damn, was I ready. We arrived at the camp to find three guys already there and waiting. Bobbie was given a nice warm welcome, some nice appraising looks and major attention. Ron started a fire in the fireplace; we all got acquainted and relaxed a little. I gave almost all of my attention to Ron; the others were there to fuck me but, I was his. When we became a little loving with each other, everyone started to get interested. As he kissed and groped me, they all got the idea and things started to happen. He made it known that he would be first in line; I was to be treated with some respect but ... to be used by everyone, as much as they wanted. Ron and I would be sleeping together.

We had brought some food and, there was a little store a few miles away. We didn’t know about the others but, Ron and I had planned on being there a few days. I would do most of the cooking and cleaning-up; just like a girl. As we settled in, once things started to get warm and comfortable, from the fire, Ron led me to an armchair.

Once I was in his lap, when the kissing and petting started, a few more guys arrived and everyone was interested in watching. I went into ‘girl’ mode with him, we became very passionate and, my panties came off easily. Once I fished his hard cock out, there was a lot of interest as I straddled him then, eased down on his rock hard cock. I spent about half an hour riding him while in the perfect position to suck any cock that was shoved in my face. Most of the guys were good and horny, I was more than willing. By the time Ron pumped a nice load into me, I’d swallowed at least three more.

Most of the guys took the hint and, at least got naked from the waist down – I was looking at some nice hard cocks. One of them belonged to Bill, our black friend. He’d been growing over the past few years and, was now, almost nine inches of thick black cock with a beautiful fat head! He was, without a doubt, the biggest cock in the room. As I was riding Ron, he’d come over and kissed me then remarked, “You look good tonight ... I’m gonna drill that hole of yours next.” He gently slapped my face with it, a few times then, stood stroking slowly as I finished riding Ron. By the time I got off of Ron’s lap I was relaxed, gaping just a little and ready for Bill. Everyone else watched as he walked me to the big kitchen table, gave me a wet passionate kiss then, turned me around and bent me over the table. He lifted the dress, I spread my legs for him and clung to the table waiting. Since I was now leaking, it was simple for him to find my cunt and ease right in ... god did he ease in, hit bottom and started a nice easy fucking. I moaned, gasped and squealed while he went at me with a purpose. The others stood stroking and watching as I was given a wonderfully slow and deep reaming.

That first night was a blur of cocks, mouthfuls of cum and an endless stream of cocks being shoved into my waiting cunt. A few hours later I had cum in my hair, on my face and some splattered on the front of the dress. My little cunt was gaping and I was leaking like hell. I don’t remember exactly (who would) but, I think that there were seven or eight that first night. Some of them did me twice. I’d been face-fucked a few times and, although sore, was glowing all over. I did know that Bill had done me twice. The second time I was on my back, on a rug on the floor, with my legs over his shoulders while he fucked me harder than ever! By then he just felt good ... I know I screamed my head off during that one and ... was close to an orgasm a few times!

When it was over, it wasn’t over ... yet. I changed into the nightgown while relaxing and talking; sitting in Ron’s lap. He got another erection and, said it was our bedtime, I agreed with him. He took me by the hand, we said good night and headed for the one private bedroom. After some cuddling and some foreplay, I found myself on my back again. Nightgown up around my hips, legs wrapped around him, as he rode me once again. That time, there was way to contain my pleasure as I had a very nice orgasm. No one missed the screaming and moaning as I blew a little load all over my tummy; that was a great one!

The next two days were nothing but sex. I spent a lot of time on my knees, on my back (or on all fours) or bent over something to get fucked. In the end, ten guys showed up; that was more than enough. I spent most of my time in panties and a t-shirt (wet panties). I’d go to sleep, gaping after a final good screwing from Ron; wake up (sort of tight again) then, take his morning wood, handle a few of the others and, right back to leaking and gaping as I made breakfast. I had goose bumps most of the time and, just glowed from all of the sex. That was one hell of a birthday gift ... ten was more than enough.

I didn’t eat much and spent only a little time on the toilet. Most of the ‘urges’ were just cramps, I’d cleaned myself out very well (beforehand). By Monday morning I’d had at least four massive orgasms, the inside of my clit burned when I peed. That was normal and would go away in a few days. By then we were down to six guys and Bill was one of them; I was getting that nice black cock three or four times a day! I don’t know which of us was enjoying it more. I was so lubed and relaxed that it was like fucking a nice wet cunt by then. He had also started to kiss me more and more ... that was very nice, I loved it!

By Tuesday morning it was down to just Bill and us. When the last guys left (just after breakfast) I was led back to the bedroom by Ron. Bill joined us for over an hour of pure lust as I was soundly fucked into oblivion once again. I was loving every second of it ... sore all over but, happy as hell.

Sweet sixteen, kissed, slobbered over and, very well fucked!

It took about a week for my body to return to normal. Hell, I needed a week just to recover! It would have been sooner but; Ron took me parking a few days later. What he’d watched, still had him pretty horny just thinking about it! We went to a nice secluded field, on the other side of our farm, spread out the blankets and made love for a few hours.

That was a very nice birthday!

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