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Member Since: 17-Dec-12
Location: US
Posts: 78
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A true story from my past that is driving a new fantasy...
Recently I began having what most people would consider a rather bizarre fantasy.

Many years ago, as a horny adolescent, I began a homosexual affair with a cousin. Just a bit younger than me, he nonetheless initiated the “experimentation” as we called it. We repeatedly assured ourselves we weren’t homosexuals, just young teens with raging hormones and no female outlets. I began to wonder, however, whether he’s done some previous experimenting of his own, because he kept coming up with ideas I’d never thought of. All of his ideas were good, it turned out, and it became harder and harder to convince myself we weren’t really simply queer.

We quickly passed though the requisite stages of boy-boy sex play: mutual masturbation, tentative cock-sucking, and then actual (the horror) penetration. He was the first to receive ropey spurts of my young semen, followed a few days later by reciprocity. Due to size differences, we eventually settled in a routine where I was “the girl” as we put it, and over a few years I received over a hundred of his deposits. I have fond memories of the couplings I recall, and wish I remembered them all.

One session in particular relates to the fantasy I mentioned at the start of this story, as it involves his sister. She was older than me, and while another female cousin was the usually imaginary partner in my heterosexual daydreams, his sister did make occasional appearances. One winter afternoon, near the end of my affair with her brother, I decided to spice up our coupling by dressing in some of her lingerie. He wasn’t particularly interested in this, but I certainly was. Laying on his mom’s bed, dressed in his sister’s hose and nightie and sock-stuffed bra, with his skinny Vasaline-coated cock slowly making it’s wan in and out of my butt remains my favorite memory.

To be continued…


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cissybiboi
Wish there was more to this hot post.

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Member Since: 17-Dec-12
Location: US
Posts: 78
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There is more.

Wanting to experience as much as possible what a woman would feel, i tried to make every detail right. And that meant I needed some type of birth control. In our prior ramblings around his house we'd found only one old condom, and I broke it in his tight butt a couple of summers ago. Searching his mom's medicine cabinet, however, I found a can of Ortho contraceptive foam, and a plastic applicator that screwed onto the top of the can. I figured out that the applicator was a sort of syringe, and I withdrew the plunger and squirted the foam to fill the applicator.

I showed by cousin how the applicator worked, then pulled down the dark green panties I'd taken from his sister's room and lay face down on the bed. I still remember how cool the bed felt against the nylon teddy and the hose I wore.

Following my instructions yet probably still wondering why this was necessary, he smeared a dollop of Vaseline onto my rosebud, and put more on the applicator. I felt a momentary chill as the cold tip of the applicator touched me, and without the least finesse he pushed it all the way in and pressed the plunger. I think he was uncomfortable with this, or maybe just in a hurry to get his stiff penis in my butt, but i would have preferred to draw out this process as it made me feel so feminine. As he withdraw the applicator and placed it in the sink basin I couldn't help but wonder how many times it had been in him mom's pussy, and if his sister had ever tried it. I hoped she had, and decided to believe she had.

Further turned on by the coolness of the foam in my rectum, and the realism it added to my fantasy of actually being his sister, I rolled onto my back, and pulled my hose and panties further down. I wriggled down the bed until my bare butt was right at the foot of the bed and my hose-clad toes touched the floor. Without delay, my cousin approached and stood between my legs. As usual, to my dismay, he wasn't undressed only enough to do the deed. This jeans were down around his thighs, and his skinny but deliciously hard cock was protruding through the opening in his boxers.

i lifted my legs and hooked them around his hips. I would have preferred him to be shirtless, and I bet he would have enjoyed feeling my nylon hose against his back, but it was not to be. he was too self-conscious, and I was thankful we went as far as we did. I didn't have to wait long to feel the warmth of the tip of his cock pushing against my opening. Unlike several years before, he was now a young but experienced top. No longer did we stumble with "too high" and "too low" before making enetrations. With nearly a hundred penetrations of my butt under his belt, my cousin now knew the spot, the angles, and how quickly he could enter me without causing pain. In just a moment, I felt his smallish balls brush against me, and the lovely warmth of his cock displacing the cold foam. We were coupled again, and I locked my lover in place with my legs.

(Comments? I'm in the chat room now...)

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Member Since: 17-Dec-12
Location: US
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Now fully coupled, we fell into our regular routine - almost. My cousin was unromantic and methodical, pushing slowing into my butt and immediately withdrawing, almost like a robot. There was never passion or any break in his pace until he neared orgasm, and then only a pause. But, I'd had no other lover and never would have another male lover, so I didn't miss what I'd never known. I just new I enjoyed feeling his lubricated and extremely stiff cock push into me again and again. This time, however, things were different for me.

I'd been nude while he fucked me a few times before, but never had I cross-dressed in front of him. i could not tell whether he liked it or was, perhaps, bothered by it, but I was completely turned on. All my senses were heightened, and the green nylon teddy felt wickedly sensuous on my bare back as I wriggled further down against him, now that he was supporting my legs. And those legs felt oh so girlish wrapped in his sister's hose. I looked down across my chest and instead of seeing the my boring teen body, I saw 2 mounds in pushing up the nylon teddy, where his sister's silky padded bra (with some help from a few socks) simulated pokie teed breasts. I saw my hips accentuated by the sheen of the dark teddy, and I saw my cousin standing between my panty-hosed legs, rocking steadily into and out of me. I felt feminine at last.

As he fucked me (I'd like to say as he made love to me but he didn't) I became aware that even if he did not appreciate my clumsy cross-dressing his body was on autopilot, and it certainly did. There was a slight quickness in his thrusts, and his cock seemed to linger just a bit at full length before retreating, and the return stroke happened a little sooner. And my own cock was pulsing at full tumescence as i realized that my body had convinced his body that he was inside a real teen girl. No matter what he was thinking, his hormones were convinced, and they were working hard to deposit his sperm deep in this pseudo girl's boy-pussy.


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Member Since: 17-Dec-12
Location: US
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i could not resist touching my own cock, which was begging for attention. It tented the satiny teddy, producing a tent that betrayed my illusion. I pulled back the teddy, and lightly grasped my cock, and began stroking in pace with his thrusts. My boi pussy has grown accustomed to his cock now, and despite the unnaturalness it now felt perfectly natural to me. I felt made to have him inside me. In fact I longed for more of him, and pulled him as tightly into me as he would go.

Per our normal custom, he indicated to me that he was nearing orgasm. Apparently my re-positioning to take him deeper had put him over the edge, so i quickly increased my own stroking to catch up with him. We'd mastered the simultaneous orgasm, and though I could never feel his cum shoot inside me I could always feel his cock pulsing, and as his cock pulsed the 2nd time my began. Almost perfect harmony, and I wanted it to last an hour.

It lasted, however, only the normal 8-9 pulses, and as I pulsed my own last stroke my cousin was already pinching his cock and withdrawing. The pinching was likely unnecessary, as I'm pretty sure his strong contractions has squeezed every available drop of semen deep into my boi-pussy. I sqeezed my own cock - which was very necessary to avoid messing his mom's bed - and lay there in repose. Post orgasmic, I felt a bit silly in the lingerie, but I also still felt feminine. Unlike my lover, who hurried off to the bathroom embarrassed and self-concious, I relished the act I'd just completed, and new I'd do it again.

Just then i felt the first dribble of his ropey cum from my pussy, and I too began my own rush to the bathroom.

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Member Since: 20-Mar-12
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Rick434 said: i could not resist touching my own cock, which was begging for attention. It tented the satiny teddy, producing a tent that betrayed my illusion. I pulled back the teddy, and lightly grasped my cock, and began stroking in pace with his thrusts. My boi pussy has grown accustomed to his cock now, and despite the unnaturalness it now felt perfectly natural to me. I felt made to have him inside me. In fact I longed for more of him, and pulled him as tightly into me as he would go.

Per our normal custom, he indicated to me that he was nearing orgasm. Apparently my re-positioning to take him deeper had put him over the edge, so i quickly increased my own stroking to catch up with him. We'd mastered the simultaneous orgasm, and though I could never feel his cum shoot inside me I could always feel his cock pulsing, and as his cock pulsed the 2nd time my began. Almost perfect harmony, and I wanted it to last an hour.

It lasted, however, only the normal 8-9 pulses, and as I pulsed my own last stroke my cousin was already pinching his cock and withdrawing. The pinching was likely unnecessary, as I'm pretty sure his strong contractions has squeezed every available drop of semen deep into my boi-pussy. I sqeezed my own cock - which was very necessary to avoid messing his mom's bed - and lay there in repose. Post orgasmic, I felt a bit silly in the lingerie, but I also still felt feminine. Unlike my lover, who hurried off to the bathroom embarrassed and self-concious, I relished the act I'd just completed, and new I'd do it again.

Just then i felt the first dribble of his ropey cum from my pussy, and I too began my own rush to the bathroom

What a hot story Rick, thanks for sharing buddy... grin

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Member Since: 17-Dec-12
Location: US
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Thanks. I have such fond memories of that day. We never discuss those activities anymore, and I have always wondered how he took me being dressed in his sister's lingerie. He tried to act nonchalant when I came out of her bedroom dressed, and said it was "ok" but there seemed to be a little extra in his thrusting later.

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cissybiboi
So glad i found this thread again and saw that you had finished it xx

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Member Since: 13-May-08
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What a beautiful story! I bet having all that contraceptive foam and his cum in you must have made you feel extra girly! (Cleaning up all that "mess" on the toilet later! Sigh... What we gurls do, hey? wink)

Did his sister or mom ever discover the messed up teddy or bed? What happened to your cousin? Did you ever "hook up" again or ever speak of it? (I wonder if he would be open to "relive" the experience?)

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cissybiboi
TVPanties said: What a beautiful story! I bet having all that contraceptive foam and his cum in you must have made you feel extra girly! (Cleaning up all that "mess" on the toilet later! Sigh... What we gurls do, hey? wink)

Did his sister or mom ever discover the messed up teddy or bed? What happened to your cousin? Did you ever "hook up" again or ever speak of it? (I wonder if he would be open to "relive" the experience?)


I'd love to find out to. Hope @Rick434 replies xx

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