Days gone bi
Siting in front of my pc reading these sexy, hot stories I figured I should at least share a few of mine.
I live in the same small town I grew up in. ( pop.under100,000) I moved away for some time back in the 90's, doing pretty much what ever I wanted to do. I started wearing girls cloths at a very young age, my step sister used to dress me up and parade me around as her little sister (I passed) and I enjoyed the attention both from her and from the guys she would introduce me to. I'm not a very tall guy only 5' 6" not a very big guy at all. curly brown hair green eyes.
Over the years time takes it toll, on the body, so I don't dress and just go out with girl/boy friends any more. I still go to parties with that kind of thing going on and around people that I know. It's just become to much work trying to keep a girlish figure. Sadly.
It was the late 1990's after a really bad break up, I had to put my life back together, in a one bed room apartment, used furniture and almost 5 months later, I really started to want some action. I had been working in a ware house for the last coupe years, made some friends along the way one was a guy named Bret. He was an all around good guy, not the sharpest tack, but a really cool guy. He was my work buddy , go out after work and have a few beers type buddy. Bret was a tall guy kind of a big dude, 6'3' or so not bad looking with wide shoulders. But a total dork.
We went to get a few drinks after work one friday and started talking about our ex's. I knew he had, had a bad break up a couple months before I did. I also knew he hadn't had any action in awhile cause he was such a dork. I told him I needed some help with getting some pictures for something. He asked what they were for and that's when I told him I was going to open an account on a gay dating website. He was shocked, "why the fuck would you want to do that?" he asked. I told him, "I'm going to have sex with a man. And why not? Look what my ex did to me, after being screwed over by enough of them, why not? I need you to help me get the pics I need for the account, to help me find the first guy to fuck me." "why me?" he wanted to know. I trust you to be able to keep it a secrete. You don't ask just ayone to do something like this." "We can grab some brews head over to my place take some pics, I'll open the account and no one needs to know anything about it. I trust you is why I'm asking." Let me think about he answered. A few beers later, he agreed, yeah I'll do it, why not.
I knew Bret was a bit of a prev already by all the girly mags in his apartment, not just the off the stand stuff, mags you had to go to a porn shop, or order off the net.(I Left this part out. This is one of the reasons I was going to try this with him.)
The plan was to go by his place grab some cloths and some beers and go to my place get showers, take some pics and hit the clubs.
After Bret had his shower and put on some sweat pants and T-shirt it was my turn, Before I got in the shower I told Bret, "please don't freak out when I come out of the bathroom". I took my things down from the top of the bathroom closet and started working on myself, I had already used the trimmers to trim up my body, (i've never had much body hair) I was almost hairless when I stepped out. I was wearing a pink and black plaid school girl skirt that left just the bottom of my ass cheeks showing. Open Toe Gladiator Chunky High Heels and the white school girl blouse to match. My black wig was a short cut with pig tails, dark makeup, black nail polish.
When Bret saw me his mouth dropped and he whispered "oh my gawd!'
"Whatcha think?" I asked in my softest girly voice.
I could see by the shock on his face I had completely caught him off guard.
whispering, stammering, he said "you look pretty fucking hot. Your freeking me out. but you look great."
After the wows and the OMG"s I handed him the trimmers and told him, this is were I need part of that help. (still using my soft girly voice) I explained that I can't see the back off my ass under my butt cheeks or the small of my back and I needed him to trim me there. He wasn't sure he wanted to, I bent over a living room chair and pulled him down to the floor and reminded him he said he would help. he poked my ass with the trimmers, I just laughed and said don't be affraid of it, it's not going to bite you, I took his hand and placed it on my ass cheek, he relaxed some and started trimming as best he could, I dropped the skirt and asked to get my lower back as well. I could feel his hands trembling.
I was loving his hands on me. After his trimming my lower back I got up and told him he could come sit in the bathroom with me while I shaved my leggs. I could see a bit of a hard on through the sweat pants, I sat on the edge of the tub as he started with the questions. All I said was I'd show im when I'm done.
He wanted to know how I learned to do this and how much I looked like a girl except not having tits. I teased about how he must be excited cause of the semi erection I could see under the weat pants. Well yeah, I've never seen anything like this, he said.
After trying on some of my outfits we decided on the black fishnet stocking and garters with the black and silver school girl skirt, which was just as short as the others along with the dark pixie cut wig.
We took some test pics with legs crossed, and a couple up skirts just to see how they looked on my new account, sitting in front of the pc Bret started shaking his leg next to me. I put my hand on it to stop it and brushed his semi hard cock. I showed him some of the other pages and accounts with pictures and ones that I liked. I stopped on one pic with a cock in a cross-dressers mouth. and I said, omg we could do that, as I laid my hand on his cock causing him to jump. I acted shocked omg Bret your hard, he stammered "yeah I can't help it, I've never seen anything like this.
I pressed my hand on his cock and squeezed just a little, OMG Bret I want to see it, let me see it, I was saying in my soft girly voice. Let me do that pointing to the cock in mouth picture.
I lead him back into the main room and sat him on the floor, back against the wall I got on all fours so he could get pictures of my ass and my legs. By this time I could plainly see he was excited, I crawled between his legs and said to him, "lets get that picture" I pulled down his sweats and took that beautiful cock in my mouth. it was at least 8 inches and just not as thick as a silver dollar. I bobbed my head on it a couple times taking it deep moaning at how good it felt to have that cock in my mouth. I could feel him trembling from this and he breathed deeply sucking in his air suddenly. He then asked "what are you doing"? I told him, making sure it's good and hard for the picture which he had forgotten to take. I could hear him taking pics as I sucked his cock, taking it deep and holding it in place stroking it with my tongue, a trick I had learned from a girl I knew, using a lollipop as a cock.
A few minutes of this we got back in front of the PC and loaded up the pictures, my account page was coming together. I showed Bret some more pic on other pages saying it was to get some ideas for mine. I stopped on a page that had a cock part way in the page owners boi pussy. I had to keep playing the part, I was so close to getting what I wanted. I pointed to it and said how hot that was and how good it would look on my page. Bret said something about he didn't know if he could do that. "I'm not gay" I explained to him that no one is saying your gay, your just helping out a friend like you said, and how no one could see or would know what we were doing cause I was never going to say anything.
He reluctantly. agreed, he let me lead him back into the main room on the floor back against the wall, I took him deep back into my mouth again to get his beautiful cock wet, adding some lube to my boi pussy and his cock, I got on my knees in reverse cowboi, I lowered my self down onto his cock, I had worked up my pussy with a didlo and added some lube when I had my shower, it slipped right in, the Sensation of being so stretched so suddenly after so long took my breath, I let out an almost whispered "awwwwwwwww....... " that lasted the length of his shaft entering my boi pussy.
I raised and lowered myself, taking the entire length each time, moaning softly with each stroke. I heard the camera a couple time, and whispered in my girly voice "omg Bret don't make me atop" I felt his hands on my hips, He said I wasn't sure he could fuck another guy. I asked him, "do I look like a guy to you?" "OMG, no you don't, turn around and let me see you" I raised up and turned around getting back on his cock in cowboi, he grabbed me around the waist and pulled me into him kissing me, sticking his tongue down my throat, he was working his hips along with mine, we were making good work of fucking my ass pussy together, I whispered in his ear ,Be the one to fuck me Bret. Fuck me. He was in total lust, he picked me up, cock still in me, and laid me on the couch on my back, legs up, he held my legs back with his hands just under my knees, I could feel his balls hitting my ass as he fucked me long and deep almost to the point of coming out with each stroke, going back in balls deep each time, I was moaning out of control trying to keep the girly sounding voice going.
Bret fucked me like this for some time, I had my head laid back, moaning, I could feel my eyes trying to roll back in my head. Pure lust had taken us both over, I felt the pace pick up, his strokes became shorter, and harder, he was now pounding my man pussy, my breath was coming in deep pants, he was breathing , panting almost in a growl when he said he was going to cum. my boi pussy tightened and I felt and assgasam deep from with in me, all I could do was moan the words cum in me baby , don't stop baby FUCK ME. With a final thrust I felt him go balls deep and held it there, I could feel his cock pulsing deep in my ass, pumping his juice deep inside me, I could feel each spasm, it was warming my manhole, omg there was alot, I could feel it running out before he was even done cumming. with the last spasm Bret sat back on the floor, I jumped down to his cock taking it in my mouth sucking it deep and hard to finish up his orgasm, getting it all out of him. I could feel Bret shudder with each stroke of my mouth going down on his cock, cleaning him and getting every drop.
After a twitch of his head he asked me to stop, he said he couldn't take any more. I handed him a beer, and sat next to him. He said he couldn't believe he just did that. I told him , I think you needed it. He agreed. and also said he didn't believe that was the first time I had ever done that.
The truth was out so I told him some about my past. About the girls I dress with and go out with to the gay bars all dressed up as a total slut, and that I was supposed to go with them tonight. I asked if he wanted to go as my date, and his chances of getting lucky was pretty high. His reply, only if your dressed like that and no one ever finds out.
I live in the same small town I grew up in. ( pop.under100,000) I moved away for some time back in the 90's, doing pretty much what ever I wanted to do. I started wearing girls cloths at a very young age, my step sister used to dress me up and parade me around as her little sister (I passed) and I enjoyed the attention both from her and from the guys she would introduce me to. I'm not a very tall guy only 5' 6" not a very big guy at all. curly brown hair green eyes.
Over the years time takes it toll, on the body, so I don't dress and just go out with girl/boy friends any more. I still go to parties with that kind of thing going on and around people that I know. It's just become to much work trying to keep a girlish figure. Sadly.
It was the late 1990's after a really bad break up, I had to put my life back together, in a one bed room apartment, used furniture and almost 5 months later, I really started to want some action. I had been working in a ware house for the last coupe years, made some friends along the way one was a guy named Bret. He was an all around good guy, not the sharpest tack, but a really cool guy. He was my work buddy , go out after work and have a few beers type buddy. Bret was a tall guy kind of a big dude, 6'3' or so not bad looking with wide shoulders. But a total dork.
We went to get a few drinks after work one friday and started talking about our ex's. I knew he had, had a bad break up a couple months before I did. I also knew he hadn't had any action in awhile cause he was such a dork. I told him I needed some help with getting some pictures for something. He asked what they were for and that's when I told him I was going to open an account on a gay dating website. He was shocked, "why the fuck would you want to do that?" he asked. I told him, "I'm going to have sex with a man. And why not? Look what my ex did to me, after being screwed over by enough of them, why not? I need you to help me get the pics I need for the account, to help me find the first guy to fuck me." "why me?" he wanted to know. I trust you to be able to keep it a secrete. You don't ask just ayone to do something like this." "We can grab some brews head over to my place take some pics, I'll open the account and no one needs to know anything about it. I trust you is why I'm asking." Let me think about he answered. A few beers later, he agreed, yeah I'll do it, why not.
I knew Bret was a bit of a prev already by all the girly mags in his apartment, not just the off the stand stuff, mags you had to go to a porn shop, or order off the net.(I Left this part out. This is one of the reasons I was going to try this with him.)
The plan was to go by his place grab some cloths and some beers and go to my place get showers, take some pics and hit the clubs.
After Bret had his shower and put on some sweat pants and T-shirt it was my turn, Before I got in the shower I told Bret, "please don't freak out when I come out of the bathroom". I took my things down from the top of the bathroom closet and started working on myself, I had already used the trimmers to trim up my body, (i've never had much body hair) I was almost hairless when I stepped out. I was wearing a pink and black plaid school girl skirt that left just the bottom of my ass cheeks showing. Open Toe Gladiator Chunky High Heels and the white school girl blouse to match. My black wig was a short cut with pig tails, dark makeup, black nail polish.
When Bret saw me his mouth dropped and he whispered "oh my gawd!'
"Whatcha think?" I asked in my softest girly voice.
I could see by the shock on his face I had completely caught him off guard.
whispering, stammering, he said "you look pretty fucking hot. Your freeking me out. but you look great."
After the wows and the OMG"s I handed him the trimmers and told him, this is were I need part of that help. (still using my soft girly voice) I explained that I can't see the back off my ass under my butt cheeks or the small of my back and I needed him to trim me there. He wasn't sure he wanted to, I bent over a living room chair and pulled him down to the floor and reminded him he said he would help. he poked my ass with the trimmers, I just laughed and said don't be affraid of it, it's not going to bite you, I took his hand and placed it on my ass cheek, he relaxed some and started trimming as best he could, I dropped the skirt and asked to get my lower back as well. I could feel his hands trembling.
I was loving his hands on me. After his trimming my lower back I got up and told him he could come sit in the bathroom with me while I shaved my leggs. I could see a bit of a hard on through the sweat pants, I sat on the edge of the tub as he started with the questions. All I said was I'd show im when I'm done.
He wanted to know how I learned to do this and how much I looked like a girl except not having tits. I teased about how he must be excited cause of the semi erection I could see under the weat pants. Well yeah, I've never seen anything like this, he said.
After trying on some of my outfits we decided on the black fishnet stocking and garters with the black and silver school girl skirt, which was just as short as the others along with the dark pixie cut wig.
We took some test pics with legs crossed, and a couple up skirts just to see how they looked on my new account, sitting in front of the pc Bret started shaking his leg next to me. I put my hand on it to stop it and brushed his semi hard cock. I showed him some of the other pages and accounts with pictures and ones that I liked. I stopped on one pic with a cock in a cross-dressers mouth. and I said, omg we could do that, as I laid my hand on his cock causing him to jump. I acted shocked omg Bret your hard, he stammered "yeah I can't help it, I've never seen anything like this.
I pressed my hand on his cock and squeezed just a little, OMG Bret I want to see it, let me see it, I was saying in my soft girly voice. Let me do that pointing to the cock in mouth picture.
I lead him back into the main room and sat him on the floor, back against the wall I got on all fours so he could get pictures of my ass and my legs. By this time I could plainly see he was excited, I crawled between his legs and said to him, "lets get that picture" I pulled down his sweats and took that beautiful cock in my mouth. it was at least 8 inches and just not as thick as a silver dollar. I bobbed my head on it a couple times taking it deep moaning at how good it felt to have that cock in my mouth. I could feel him trembling from this and he breathed deeply sucking in his air suddenly. He then asked "what are you doing"? I told him, making sure it's good and hard for the picture which he had forgotten to take. I could hear him taking pics as I sucked his cock, taking it deep and holding it in place stroking it with my tongue, a trick I had learned from a girl I knew, using a lollipop as a cock.
A few minutes of this we got back in front of the PC and loaded up the pictures, my account page was coming together. I showed Bret some more pic on other pages saying it was to get some ideas for mine. I stopped on a page that had a cock part way in the page owners boi pussy. I had to keep playing the part, I was so close to getting what I wanted. I pointed to it and said how hot that was and how good it would look on my page. Bret said something about he didn't know if he could do that. "I'm not gay" I explained to him that no one is saying your gay, your just helping out a friend like you said, and how no one could see or would know what we were doing cause I was never going to say anything.
He reluctantly. agreed, he let me lead him back into the main room on the floor back against the wall, I took him deep back into my mouth again to get his beautiful cock wet, adding some lube to my boi pussy and his cock, I got on my knees in reverse cowboi, I lowered my self down onto his cock, I had worked up my pussy with a didlo and added some lube when I had my shower, it slipped right in, the Sensation of being so stretched so suddenly after so long took my breath, I let out an almost whispered "awwwwwwwww....... " that lasted the length of his shaft entering my boi pussy.
I raised and lowered myself, taking the entire length each time, moaning softly with each stroke. I heard the camera a couple time, and whispered in my girly voice "omg Bret don't make me atop" I felt his hands on my hips, He said I wasn't sure he could fuck another guy. I asked him, "do I look like a guy to you?" "OMG, no you don't, turn around and let me see you" I raised up and turned around getting back on his cock in cowboi, he grabbed me around the waist and pulled me into him kissing me, sticking his tongue down my throat, he was working his hips along with mine, we were making good work of fucking my ass pussy together, I whispered in his ear ,Be the one to fuck me Bret. Fuck me. He was in total lust, he picked me up, cock still in me, and laid me on the couch on my back, legs up, he held my legs back with his hands just under my knees, I could feel his balls hitting my ass as he fucked me long and deep almost to the point of coming out with each stroke, going back in balls deep each time, I was moaning out of control trying to keep the girly sounding voice going.
Bret fucked me like this for some time, I had my head laid back, moaning, I could feel my eyes trying to roll back in my head. Pure lust had taken us both over, I felt the pace pick up, his strokes became shorter, and harder, he was now pounding my man pussy, my breath was coming in deep pants, he was breathing , panting almost in a growl when he said he was going to cum. my boi pussy tightened and I felt and assgasam deep from with in me, all I could do was moan the words cum in me baby , don't stop baby FUCK ME. With a final thrust I felt him go balls deep and held it there, I could feel his cock pulsing deep in my ass, pumping his juice deep inside me, I could feel each spasm, it was warming my manhole, omg there was alot, I could feel it running out before he was even done cumming. with the last spasm Bret sat back on the floor, I jumped down to his cock taking it in my mouth sucking it deep and hard to finish up his orgasm, getting it all out of him. I could feel Bret shudder with each stroke of my mouth going down on his cock, cleaning him and getting every drop.
After a twitch of his head he asked me to stop, he said he couldn't take any more. I handed him a beer, and sat next to him. He said he couldn't believe he just did that. I told him , I think you needed it. He agreed. and also said he didn't believe that was the first time I had ever done that.
The truth was out so I told him some about my past. About the girls I dress with and go out with to the gay bars all dressed up as a total slut, and that I was supposed to go with them tonight. I asked if he wanted to go as my date, and his chances of getting lucky was pretty high. His reply, only if your dressed like that and no one ever finds out.
3 years ago
