The Next Step
In my last semester of high school, I persuaded my mom to help me find a doctor to discuss a real transition to a more feminine form. I was tired of having no breasts and all that body hair was a pain to keep shaved. The first two doctors would not even discuss a partial transition and insisted on a very prolonged process including 3 months of therapy, 18 months of living as a woman, then hormones and surgery. I finally convinced the third doctor that I didn't need therapy because I had essentially lived as a woman, albeit a bisexual one, for a very long time. He agreed to begin hormone treatments and I got electrolysis for a quick solution to the hair problem. The breasts would have to wait a while. My mother refused to pay for that - she couldn't bring herself to take that step while I was still a student. My father had left me an education trust that would pay for an expensive private university, but if I got scholarships, I could keep the money. I had already cinched over $30,000 in scholarships with my 3.9 GPA and my 1455 SAT score, so I knew I could eventually afford the breast implants. What I didn't tell the doctor was that I did not intend to ever finish the job. My goal was to become a woman in every way except for removing the penis. I had to maintain a fully functional cock.
Judy and Heather noticed the changes in me before anyone else. They loved the softening effect, the lack of body hair, and the change in my voice. They started dressing me and taking me to places normally reserved for women. I was excited to see that no one paid any attention except the men who hit on me. Heather was pissed when a gentlemen she had her eye on asked me out. I told him I was in a relationship so Heather finally got her man. Based on her accounts, she got her man three times, then shared him with Judy..
My last semester, I couldn't wear dresses, but they didn't complain about the undergarments anymore. I still got some harassment, but that slowly subsided. Jaden stopped getting grief for hanging around me and he and I continued to have the occasional roll in the hay. Carson had not had sex with me for months since I spent so much time with Howard and the girls. One day I went to see Jaden, actually hoping to see my favorite lady, Jane. Neither Jane or Jaden was home, but Carson was there, cleaning out the pool house which had gotten some water damage in a storm. When he saw me, he gasped. He couldn't believe how feminine I looked, especially with my short skirt and a man's shirt unbuttoned and tied, exposing my sexy tummy.
He kissed me deeply and squeezed my ass, causing us both to harden down below. He told me that Jane and Jaden had gone to Boca Raton to help Jane's mother move some things into a storage unit. Carson had stayed behind to work on the damaged pool house. I was surprised when he told me that he had company coming by. He was hesitant to tell me that it was a new male lover he had found. I assured him that I was not jealous and was happy that he was able to find a way to meet his needs for male sexual contact. He told me that he had gone to a club in South Beach, while Jane was out of town, and had met Greg in the restroom. They danced for a while and things got hotter. Greg kissed him and stroked his cock while they danced and then went to a hotel with him for a few hours of hot sex. I told him I was very happy for him and assured him I would vacate before his lover arrived. Suddenly, he had a brainstorm. He wanted me to watch them while they had sex, like I had done with him and Jane. I told him that I didn't feel comfortable with it anymore. Then he came up with another idea that I did like.
When Greg arrived, I was watching from inside the main house. He was tall, with dark hair and a fairly muscular build. Carson had told me that he was 28. His ass looked great in his tight pants. Carson hugged him and led him inside the pool house. I went to the pool house window and peeked inside. They talked briefly, then Greg undressed revealing a thick, circumcised, six-inch cock. Carson went down on him and adjusted their position so I could watch him suck and he could see me watching. He was really working on Greg's cock, deep throating him over and over again.
Suddenly Carson, jumped up and pointed at the window, yelling something that I couldn't hear. He ran out and grabbed me dragging me forcefully inside. Greg was freaking out and Carson screamed "You little peeping tom bitch, what do you think you're doing watching other people's private affairs?" Greg was scared of what Carson might do and said "Maybe we should let the cops deal with her, Carson."
"Exactly what would I tell them Greg? She was spying on me and my male lover? Are you crazy?"
"Ok, calm down Carson"
"No Greg, I think I'm going to teach this little cunt a lesson that she won't forget."
"Carson, I won't be involved in beating up a teenage girl."
"Shut up, Greg. I'll handle her."
Turning to me he yelled "Get on your knees, cunt." He was very convincing and I followed his lead. "Unzip me and take out my cock you little whore." He said forcefully. I was getting hot and had to work hard to appear scared. "Ok" I said and pulled out his cock. "Call me master, you little cunt." he barked. "Yes master" I responded, "What are you going to do to me master?" "I'm going to do what I please, slut, now suck my cock." "Yes master" I said and began to blow him tentatively. "Take it all, cunt" he said and grabbed my head shoving his cock down my throat. I pretended to gag and I could see Greg's cock beginning to harden. Carson got on his knees and continued to feed me his cock very forcefully. He turned to Greg and said "Get behind her and fuck her pussy."
He looked scared and said he couldn't do it. Carson yelled "You do it you cocksucker or I'll never see you again." "Good bluff" I thought to myself as Greg moved behind me, stroking himself. "Lift her skirt so I can see it go in." Carson ordered. "Tell him you want that cock, cunt." he barked. "Please don't look under my skirt master" I begged, trying not to laugh. "Why not?" Greg said curiously. "Please don't fuck me, master." I moaned pitifully. By now Greg was very curious and raised my skirt for a peek. "Oh my God, Carson. This she is a he." "Really?" Carson asked and looked for himself, feigning surprise at my large package. "That's even better. Fuck the bitch's ass" Carson said to Greg forcefully. Greg was now hard as a rock and slipped on a condom. When he started fingering and lubing my ass, I pretended that I couldn't take it. "Please stop, master. Don't shove that thick cock up my tight little asshole. I can't take it." I begged. By that time, he was too far gone to care and he placed the head at my entrance and pushed. I squeezed my muscles making it very difficult for him to penetrate me. It finally slipped in and he started working it up my steamy tunnel. I slowly stopped squeezing and he kept pushing. Before long, I was fully mounted and he started a steady rhythmic fucking motion sliding almost out then smoothly back in, slapping me with his balls.
About that time, Carson yelled "Take my cockjuice you cum-swallowing whore." and shoved his cock in to the limit spewing semen in my mouth and throat. I was really getting off on this scene and Greg was giving me a great assfucking. He held my hips firmly and "stirred" my ass with his sweet sausage. Then Carson surprised us by moving into a 69 position with me. "Clean up my cock, bitch while I taste your big clit." he ordered. I was happy to oblige and Greg started moaning as Carson licked my balls and his cock. Greg started panting and grunting as his orgasm approached. Just before Greg blasted my ass, Carson pulled his cock out, ripped off the condom, and took Greg's cock in his mouth. Greg humped his face and showered his mouth and face with thick, white semen.
Next, Carson laid me face up on a workbench he had set up and my legs and head hung over each end. Carson asked Greg to suck him hard again and Greg obliged. Then Carson rubbered up and slipped his cock in my ass to the hilt. Greg walked around and shoved his still-dripping cock in my mouth and said "Suck it, boy toy:". He was really getting into the spirit now. I let him use my mouth as a fuckhole, milking the shaft as he fucked my face. They got a good rhythm going and took turns calling me "cunt", "slut", and "whore". It was kinky, but fun for me.
Greg pulled out suddenly and climbed on top of me, slipping a rubber on my cock. Then he faced me and sat on my big dick, slowly sliding down my shaft and rocking to loosen his tight hole. Carson had a great rear view as he continued to pound my boycunt with his big prong. He fondled my balls as Greg rode my fuckstick. I can't imagine a more sexually-charged environment and we all were feeling it. Greg leaned forward and forcefully stuck his tongue in my mouth tasting the mix of his and Carson's cum that remained. The scene was so erotic that I started to cum. Greg jumped up and removed my condom and ate my cum as Carson pumped my load in his mouth with his right hand. Then Carson and Greg moved around and pumped their second loads into my open mouth.
They left me on the table and sat down to rest. Carson had another brainstorm and used a curtain pull to tie me up with my legs spread, feet on the floor, bent over with my stomach flat on the workbench. He said I would be their fuckhole for the evening and they began working on the pool house. They would work for a while then one or the other would see me, get horny, and come fuck my ass. They each fucked me twice more, then 69ed each other to orgasm right in front of me. I had cum twice while they fucked me and Carson gave me one final blowjob. It was getting late and Greg was starting to come back to his senses, worried about what I might say. When Carson broke down and told him the truth, he was angry and relieved at the same time. He started to apologize for the harsh treatment, but I told him it was sexy knowing that Carson would not let it go too far.
Greg invited us both to a party being held for Gianni Versace (such a tragic loss) the next night at someone's home in South Beach, but Carson could not go. I accepted eagerly and went with Greg as his date. Elton John was there and I got to meet him. It was exciting as hell and the large crowd was very eclectic. There was great food and wine and a lot of sexy men and women. I went dressed as a woman and was surprised to find a hot-looking woman goosing my ass on the terrace. I asked her how she knew I was a man and she said that she didn't, but that would eliminate the need for me to wear a strap-on. I told her that I was there with Greg and she told me to bring him along. I found him and told him what had happened. He had met another sexy guy and brought him too. The first two bedrooms we found were occupied with other people having fun, but the second group invited us to join them. It was a sexy couple and things got very wild. However the wildest part was when Julianna, the girl from the terrace, took off her thong and revealed a gorgeous seven-inch uncut cock. I almost came when I saw it. She had beautiful tits, a pretty feminine face, a hot ass, and a beautiful cock.
The sex that night was great. Rona, who turned out to be the only real girl in the bedroom, ended up getting fucked in every orifice repeatedly and she loved every minute of it. I got my share too with every cock finding its way into my mouth and ass. After Rona and her date Garrett left (both with a mouthful of cum and sore asses), the others started passing me around taking turns reaming my ass. I fucked Julianna once and I loved reaching around to rub and squeeze her tits or stroke her big dick. I came like a firehose in Greg's mouth. We didn't leave until 2 AM and when Greg dropped me off at home he sucked me off in the car before I got out. When I came, it was almost painful. He was almost as insatiable as me.
Graduation was almost a welcome relief. I was accepted at a medium-sized private school in Coral Gables that has a great football team (no more hints). That summer was a bit of a sexual blur. Between Howard, Jaden, Carson, Greg, and all of Greg's friends, I was very satisfied. I was also happy about staying close to home so I could continue to see my sexy companions. Since freshman were required to stay on campus, I was assigned to a dorm - a male dorm. Things got dicey immediately. My new roomie freaked out when he realized I was going to be living as a woman. He asked to have me removed and the university was at a loss as to how to handle it. The situation was resolved quickly when another student volunteered to room with me. I insisted on meeting him and was pleasantly surprised to find a very nice, attractive, seemingly intelligent senior business major (like myself). He was quite wealthy, coming from a well-to-do family and having inherited a great deal of money when he turned 21. Because he was a senior, and school contributor, he had a special room with two separate bedrooms, a private bath, and a small living room.
During the fraternity / sorority rush period, I was surprised to receive two rush party invitations. The first was from a sorority, when a member saw me on campus and thought I was a woman. This sorority was known for its attractive women, so I was very flattered. Of course I declined. An informal gay fraternity also approached me and I accepted their party invitation. I had visions of interesting fraternity parties. When I arrived at the party I was only mildly surprised to find that my new roomie, Gary, was a member. The party was a bit subdued, but everyone was nice. I realized that many of the members were either recently out of the closet or firmly entrenched in public. Most of them had had very little sexual experience. Also, they did not want to call attention to the small house for fear of harassment.
The hazing was somewhat predictable, childish stuff, until the final test. The last night, we were forced to kneel blindfolded and naked in the living room and perform oral sex on various vegetables and fruit, then identify it. When we got to the obligatory cucumber, it was about ten inches long. I heard gasps when I deep throated it and closed my mouth with it inside. Needless to say, I was quickly a popular member of the fraternity. That night, back at the room, Gary told me that the cucumber stunt had raised some eyebrows and hardened some cocks too. I reached over and rubbed his and asked him what he had thought of it. He said his reaction was pretty much like the one he was currently having, a very stiff cock. I asked him if he would like a private demonstration and he responded by dropping his pants and briefs, revealing a very thick, six-inch love log. I removed my skirt and top, leaving me in crotchless panties and a lacy padded bra. When I took his cock in my mouth I realized that he was not experienced. When I finally took it all the way down, he came in my mouth almost immediately.
"Can you teach me to do that?" he asked earnestly. "Certainly." I said and proceeded to give him a cocksucking lesson, with my cock being the final exam. He did well after a few gags and coughs and the occasional biting. When he got the hang of it, he really got into it. He sucked me to a roaring orgasm, then kept it in his mouth until it hardened again and sucked another load out of me. I was very pleased with my roomie. We slept in his bed that night and I let him fuck me (another first for him). I sucked all of his cum from the rubber, and he was riveted by that. The next morning we showered together and he fucked me again, then sucked me off.
After that night, things got more interesting at the frat house. Apparently, Gary became a convert and went forth to train others. By the next big party, the gang had gotten a bit more daring. Almost every senior and junior member invited me to a bedroom for some private time. I took one guy up on it and we had a grand time. My feminine undergarments got him so hot that he let me fuck him then cum in his mouth. We were gone for about an hour and a half. When we came back to the party, several guys were naked and in various sexual groupings. Some of the guys got scared and left. One guy was on his back, getting fucked, and asked me to suck his cock. I slid over him and got into a 69, taking his massive meat in my mouth. He was, by far the largest one there - over 9 inches and quite thick. He reminded me of Bobby and the night in the video booth.
He sucked me well and I deep throated him over and over until he shot the biggest load I'd ever taken. It poured into me and ran down my chin. This caused the guy fucking him to explode and I got some of his load too. I slipped around and took his place, fucking my new friend until his cock got hard again. Then I slipped a condom on him and sat on his giant schlong. It was painful, but so worth it. When I lifted up, his giant dick rubbed my thighs. Before long, I shot a load on his face and chest and he caught a few drops in his mouth. He continued stretching my anal cavity, sliding in and out, squeezed by my tight boycunt. I milked his stiff shaft and started talking dirty to him. When I begged him to "fuck me like a cheap whore" he suddenly exploded in ecstasy. I milked every drop into the condom, then slipped off and drank it. People all over the room were oohing and ahhing over that. His name was Gil and I decided he was going to be a close friend.
About once a month we had a party like that and word spread to other schools. We eventually had a challenge football game and party with a similar group from Florida State and a group from the University of Florida. The parties quickly degenerated into major sausagefests with lots of good fucking and sucking. I came up with a clever way to meet everyone. I laid on my back on a table with my head hanging off. Then the guys formed a line and I gave everyone a quick deep throating. There were over thirty guys there that night and I got a taste of them all. Three of them were so excited they shot a load in my mouth. After I gave Gil a few sucks, I told him to fuck me while I sucked the others. While I did the remaining cocks, Gil reamed out my ass good then fed me his cum.
When I was done sucking, the boys brought out a surprise for me - a real girl, totally nude. It was supposed to be a joke, but she was a real "fag hag". She was very attractive and had huge tits. She sat on my face and sucked my cock like a pro. Then she told me to fuck her ass like I would one of the guys. I gave her a very sensual fucking with lots of rubbing on her tits and ass. She moaned continuously. When I got close, she put my cock between those big jugs and titfucked me to an orgasm, most of which she got in her mouth. I found out later that she was a hired stripper. She gave me her card and said I could have a freebie anytime I wanted. I got together with her twice after that and buttfucked her both times.
If you or someone you know has been with Tess, please email me at twonight@excite.com and tell me about it. I am very interested to compare your account with her journal entries.
Check out my fiction stories too (The Awakening, Black Dorm, Star Cruiser, and Olympiad), and my own true story (Shocking Encounter).