-
Dating Disasters
-
Transsexual Female / 22
My Worst Date
I was 19, proud of my hormone induced growing buds on my chest. They were almost an A cup, puffy nipples, 1 inch wide areolae. They were very sensitive, my nipples would get hard at anything almost. The hormones made my already thin clit shorten up. It was about the size of my little finger and very easy to hide. I was at a resort known for being a sex retreat and also being LGBTQ and straight friendly. I wasn't prepared to go totally nude, though a transgirl did on most days. I went topless when I'd get to the beach. Todd was sitting next to me, and there were plenty of empty loungers. He was cute, and he seemed interested, when we started talking I told him about me right away that I was a transgirl and hadn't had bottom surgery.
He talked to me like he would any girl he wanted to bed, i liked it, he was perfect. Six feet plus tall, 175 lbs, cut body, and wore tight swimwear showing a rather large and thick tube in his shorts and what looked like rather large balls. After a while he asked if he should go somewhere else and I told him I didn't mind talking with him at all. He said he was wanting to get some total sun and didn't want to take off his shorts if it wasn't OK with me. I was matter of fact, with my inner self drooling to see this adonis nude. He was indeed big, about 6 inches soft and while soft almost 2 inches thick. I immediately pushed it out of my mind as I was not experience in my backside, but had sucked before. I knew I couldn't take that large a cock for sex. I mentioned after about 15 minutes that he'd better put some lotion on or he'd burn in a place where no man wants to be sunburned. He said he didn't have any lotion so I gave him mine. He couldn't get it opened so I opened it for him, he asked me if I wanted to do it. I don't know why but I did rub on his butt, then rolled him over for his front. I jacked his cock till he came. I was embarrassed and wanted to leave but not before he asked me to dinner that night.
We met at night, he was again the perfect gentlemen, we slow danced, talked, ate and at the end he suggested we take a walk on the beach in the moonlight. I was swooning, his arm around my waist on the beach, and he slipped it down to my butt, squeezing, and I told him I couldn't do that. After a while he asked why and I told him I was totally inexperienced back there. He asked about my mouth, and I admitted I'd done that with 2 boys, one for over a year, that and my hand. We ventured into the palm trees and we got quite far away from everyone else, he was very matter of fact, he said "Pull your panties down and bend over that fallen tree". I was in shock to say the least, I just looked at him and he repeated himself and said not to make him say it again or he'd hurt me. Hesitating, he slapped me twice really hard in the face and pulled down my dress to see my boobies, pushed me over the tree and yanked down my panties, ripping them in the process. I was just thinking that they were $40 panties and he ripped them when I felt the lubed head of his cock at my hole. "You're going to be my little slut you cocktease" he said and he pushed it in all the way and grabbed me over my mouth to muffle my screams. He held it in me firmly and told me not to say anything, I couldnt' anyway I was crying too much. He held it I kept contracting my muscles to ease the pain. Eventually he started his fucking me. He reached around with both hands and played with my little puffies and fucked for at least 15 minutes before he shot it all inside me.
He immediately pulled out and I turned around and saw his erect cock before it went down, it was so big, and my butt hurt so much, it was like everything was shoved deep back inside me I actually felt bloated. "Now baby, you can play as much of that hot little tease you want, but you've been had, you've been fucked and you're going to get more unless you want me to hurt you some more". He announced that I was his as much as he wanted and there was nothing a little bitch like me could do about it. He made me smile and hold his hand when we walked back up to the hotel and into the elevator. I stayed the next four days with him in his room, at the beach with him we were both nude. I was sucking at least once a day and got fucked a minimum of twice a day. At the end of his stay, he took me back to my room, fucked me and left.
I ended my trip a week early and went home. I had been forced to be his sex partner and there was nothing I could do about it, he never left me alone for a minute. I was hit a few times and he threatened to push his whole hand inside me if I gave anyone any indication I wasn't with him of my own accord.
It's been two and a half years, I am a natural hormone B cup now, I finally let another man into my life. I decided I never want bottom surgery, I guess it's bad enough having two places for a man to insert, I don't want three. My boyfriend is fine with it. I might tell him about my experience one day.
He talked to me like he would any girl he wanted to bed, i liked it, he was perfect. Six feet plus tall, 175 lbs, cut body, and wore tight swimwear showing a rather large and thick tube in his shorts and what looked like rather large balls. After a while he asked if he should go somewhere else and I told him I didn't mind talking with him at all. He said he was wanting to get some total sun and didn't want to take off his shorts if it wasn't OK with me. I was matter of fact, with my inner self drooling to see this adonis nude. He was indeed big, about 6 inches soft and while soft almost 2 inches thick. I immediately pushed it out of my mind as I was not experience in my backside, but had sucked before. I knew I couldn't take that large a cock for sex. I mentioned after about 15 minutes that he'd better put some lotion on or he'd burn in a place where no man wants to be sunburned. He said he didn't have any lotion so I gave him mine. He couldn't get it opened so I opened it for him, he asked me if I wanted to do it. I don't know why but I did rub on his butt, then rolled him over for his front. I jacked his cock till he came. I was embarrassed and wanted to leave but not before he asked me to dinner that night.
We met at night, he was again the perfect gentlemen, we slow danced, talked, ate and at the end he suggested we take a walk on the beach in the moonlight. I was swooning, his arm around my waist on the beach, and he slipped it down to my butt, squeezing, and I told him I couldn't do that. After a while he asked why and I told him I was totally inexperienced back there. He asked about my mouth, and I admitted I'd done that with 2 boys, one for over a year, that and my hand. We ventured into the palm trees and we got quite far away from everyone else, he was very matter of fact, he said "Pull your panties down and bend over that fallen tree". I was in shock to say the least, I just looked at him and he repeated himself and said not to make him say it again or he'd hurt me. Hesitating, he slapped me twice really hard in the face and pulled down my dress to see my boobies, pushed me over the tree and yanked down my panties, ripping them in the process. I was just thinking that they were $40 panties and he ripped them when I felt the lubed head of his cock at my hole. "You're going to be my little slut you cocktease" he said and he pushed it in all the way and grabbed me over my mouth to muffle my screams. He held it in me firmly and told me not to say anything, I couldnt' anyway I was crying too much. He held it I kept contracting my muscles to ease the pain. Eventually he started his fucking me. He reached around with both hands and played with my little puffies and fucked for at least 15 minutes before he shot it all inside me.
He immediately pulled out and I turned around and saw his erect cock before it went down, it was so big, and my butt hurt so much, it was like everything was shoved deep back inside me I actually felt bloated. "Now baby, you can play as much of that hot little tease you want, but you've been had, you've been fucked and you're going to get more unless you want me to hurt you some more". He announced that I was his as much as he wanted and there was nothing a little bitch like me could do about it. He made me smile and hold his hand when we walked back up to the hotel and into the elevator. I stayed the next four days with him in his room, at the beach with him we were both nude. I was sucking at least once a day and got fucked a minimum of twice a day. At the end of his stay, he took me back to my room, fucked me and left.
I ended my trip a week early and went home. I had been forced to be his sex partner and there was nothing I could do about it, he never left me alone for a minute. I was hit a few times and he threatened to push his whole hand inside me if I gave anyone any indication I wasn't with him of my own accord.
It's been two and a half years, I am a natural hormone B cup now, I finally let another man into my life. I decided I never want bottom surgery, I guess it's bad enough having two places for a man to insert, I don't want three. My boyfriend is fine with it. I might tell him about my experience one day.
