The Butterfly Emerges
When Gary heard that I was planning to get breast implants, he got very excited. The thought of me with big tits was very exciting to him, since we now slept together anytime we weren't sleeping with someone else. Occasionally, we even shared lovers. He loved the idea of squeezing female breasts while stroking a male cock. I told him I had to wait until the next semester for my semiannual trust fund disbursement, but he wouldn't wait. He insisted on paying and I reluctantly agreed.
Over the Thanksgiving holiday period, I finally got my implants. By the beginning of the next semester, the healing was virtually complete. My new large-C-cup tits gave me a 38 inch bustline to go with my 26 inch waist and 36 inch hips. I wasn't sure how my friends would react to seeing me in the flesh, but the results were shocking.
Suddenly, guys that I had always thought to be straight were swarming around me. Other than the surprise between my legs, I was a total female. I began wearing low-cut tops to show off my new friends and it drove men wild. All of my old sex buddies were constantly after me to see them and they couldn't take their eyes (or hands) off them. Heather and Judy almost sucked my nipples off in a marathon day of sex at my dorm. They loved my new tits. Gary loved titfucking me and squirting cum on them for me to lick off. Everyone wanted to suck my tits and they loved the feel of them rubbing their backs when I fucked them.
Howard and Jaden loved me in my black, crotchless tights and boustierre. I surprised them one day, meeting them both at Howard's place, dressed as a young schoolgirl with the short plaid skirt and long, white socks. We played a little game of headmaster and assistant disciplining the naughty schoolgirl. They spanked my bare ass, then made me suck their cocks while wearing the outfit, minus the panties. They fingered my girlish asscunt and then rubbed my big clit under the skirt. Finally they unbuttoned my top, removed my bra, and bent me over the desk and gave me a "special punishment", taking turns to apply it. Finally, Howard was giving me the punishment and Jaden gave him a little of his own. I watched him impale Howard in a mirror and I shot cum all over the desk shortly after. They made me lick it off the desk, then suck theirs up too. I loved that day.
Things were a bit awkward with Gary for the most of the semester. He felt more possessive after the implants because he had paid for them. I had no intention of being monogamous and it led to a bit of tension. I offered to pay him back, but he refused to accept it. Finally he came around and we resumed sleeping together (or not sleeping). Before he graduated and left Miami, I spent a whole weekend saying goodbye. I fed him, bathed him, pampered him, and screwed his brains out repeatedly. He would be walking across the room and I would go to my knees and suck him off on the spot. I fed him chocolate sauce from my nipples and licked whipped cream (and his cream) from his cock. Every time he got hard, I offered an orifice or hand for his pleasure. When the weekend was over, I slept over 18 hours to recover.
Just When I Thought Things Couldn't Get Stranger
During the summer following my freshman year, I bumped into Dannie at Howard's place (he was out). She had heard about my implants from Heather and she had to see them, so I showed her. She lifted them felt of them, but lingered a little longer than I expected. Suddenly she leaned over and started sucking my left breast. I was shocked and it took a lot to shock me by this time. She said that she had been experimenting a bit with Heather and found breasts very enticing. I had this stupid notion that I had turned her into a Lesbian. She assured me that she still liked sex with men and to prove it she pulled off my skirt and panties and devoured my cock. "I've missed this so much" she moaned while licking and stroking me. "No one has ever fucked my ass the way you do." I was shellshocked by this unexpected, but not unwelcome, sexual assault.
She went to the bathroom and came back with lube and a condom and got herself ready for an anal intrusion. She pushed me on the carpet and straddled my waist. With little preparation, she impaled herself on my big cock. While she bobbed up and down on my cock, she rubbed my tits and called me her "sexy bitch". I was so aroused. I had missed her tremendously and this was so exciting. She jumped off and got on her hands and knees and said "Screw my hot ass, Tess.". I loved it when she talked dirty and used my new name. She kept telling me to rub my tits on her back. I discovered later that Heather used a strap-on on her ass and rubbed her big tits on Dannie's back.
I was just about to cum when I felt something on my ass. I turned and saw Howard rubbing my ass with his hand. "Doesn't anyone in this family knock?" I thought to myself, but said nothing. Dannie's head was down and she didn't know he was there. He took out his cock, put on a condom and slipped his cock in my ass. I tried to stop him without alerting Dannie, but he was determined. This was really getting high on the "weird scale". I continued to fuck Dannie's ass, but every time she opened her mouth, I cringed. "I love it when you stick that big cock all the way up my ass, baby" she hissed. I had no choice with Howard slamming my ass forward so hard.
Finally, she looked back and spotted an extra leg back there. "Who is that?" she asked, urgently. "It's Dad baby, don't stop." Howard replied. "This is freaky.", she said firmly, but kept fucking. When she came, she squeezed my cock so hard that I exploded in her ass. When she finished she rolled over and watched her father fucking her ex-boyfriend. I couldn't imagine what was going through her head until she started fingering her pussy and moaning softly. Only sex can make people act this way.
When he came, I swallowed it all. She was tempted to kiss me and have a taste, but couldn't go that far. We all sat quietly for a few minutes, no one knowing what to say. I sensed that Howard had always been attracted to his daughter, but didn't dare act on it. I think he saw this as a way to have sex with her without physical contact. I thought it was a bit odd that Dannie didn't bother to cover herself afterward. Maybe she was attracted to Howard as well. Dannie left shortly after, but I stayed to have more sex with Howard. He seemed much more aroused than usual after the earlier scene. He fucked my ass all over the bed, riding me so hard. I finally just laid flat on my stomach and raised my ass slightly so he could pump my ass as hard and fast as he wanted.
The next day, I went over to Heather's apartment and, when I knocked, she yelled for me to come in. When I entered her bedroom, she was in a 69 position with someone that I assumed was Judy, although I could not see her face. Heather looked up and asked me to fuck her ass, so I stripped and slipped on a condom. When I got on the bed and prepared to mount her ass, she raised slightly and I realized that the recipient of her cunt juices was not Judy, but Dannie instead. I wasn't prepared for that and my cock deflated as the shock set in.
Dannie reacted quickly, saying "Let me help with that." and taking my cock in her talented mouth for a quick blowjob. I became hard again quickly and Dannie helped me insert myself into Heather's sweet asshole. Dannie moved slightly so that she could lick my cock at the same time she licked Heather's cunt and asshole. It was tremendously stimulating. We kept at it a while and Dannie and Heather both had major orgasms. Dannie's face was covered in cunt juice. When I finally pulled out to shoot, Dannie, took me in her mouth and Heather swung around to lick the shaft. They shared my load, then kissed deeply, mixing their cunt juices with my cum.
We rested and Dannie and I talked a bit. She admitted that the session the day before had been very arousing and that she intentionally stayed with Heather, when Heather mentioned that I was coming over. She said that there was no way we could have a relationship, but she would love to have sex with me once in a while. I told her I would like that and we kissed deeply. The taste of everyone's juices lingered in her mouth and it was very titillating. Judy came by later and we had a great time. The girls got into a three-way daisy chain and I took turns fucking them and licking their asses.
A couple of weeks later, I stopped by unannounced to invite Jaden to a party that night. Nobody answered the door, so I walked around to see whether he was swimming. I didn't see anyone, so I started to walk away. As I turned to leave, I heard a loud groan and knew it was Jaden immediately. He was in the poolhouse, so I walked over to see who he was fucking. I peeked in and saw something that freaked me out for life. Jaden was on his hands and knees and Carson was giving him a royal assfucking. I had never considered this as a possibility and I was shocked and aroused at the same time. I fought my desire to barge in and join them. I did jerk off while I watched and left a puddle of cockjuice behind when I left. I don't know what would have happened if I had joined them.
I was supposed to meet Greg at the party, but he arrived late. He didn't tell me what the situation was with the party. He only told me that it would be very interesting. Most of the attendees were in their thirties and forties, lots of couples. There were probably 20 people there, with twelve men and eight women (and me). I had a drink and mingled talking with a nice couple in their early thirties. Suddenly, the guy (Karl) started to fondle my ass. He said, "Your ass is really firm, do you work out?" "Yes", I replied, expecting his wife (Susie) to object, but she turned the other cheek (literally) and asked "Do you enjoy anal sex?" I wasn't sure if they knew my "status" but I decided to go with it. "I love a nice, juicy dick up my ass." I said. They both smiled and said "Please party with us first.". At that point, I realized that this was a swingers group and was very excited.
Couples and threesomes began to pair off and they led me to large sofa in a corner and began to disrobe. Clothes were starting to come off all around us and the lights were dimmed. I was nervous about their reaction to my "special equipment" and when Karl gave me a deep kiss, I got concerned (and aroused). Susie removed my top and bra and started sucking my tits and rubbing my ass under my skirt. I got on my knees and started to suck Karl's cock and he started licking her pussy. I moved to his balls and started licking and sucking them. He was really getting hot and started tongue fucking Susie hard, making her squeal with pleasure. I then licked his asshole and he begged me to tongue it good. I inserted my tongue a bit and wiggled it. His asshole was not that tight, leading me to believe that he was no anal virgin. I stuck a finger in and started to fingerfuck him. He moaned and said "Fuck that ass baby. Oh, I wish we had a dildo handy."
That was my cue and I slipped off my skirt and panties, revealing my long, hard cock. They both went after it at once, licking and sucking it like they were starving. Karl whispered in my ear "Please fuck me with that big cock. I need it bad." He leaned over the sofa, on his knees and Susie sucked me and licked his ass. She helped me slip on a rubber and insert my cock, stroking me as I penetrated his tight hole. Then she straddled his back and pressed her cunt in my face. I licked and tongued her as I steadily fucked Karl's luscious, hot sheath. Susie was very short (4'10") and her tits were very large (DD), so they hung just over my head as I ate her pussy. Occasionally, I reached up and squeezed or rubbed them. After a few times, I felt something wet in my hair, and reached up to see what it was. I tasted it and realized it was milk. She was lactating and for some reason, I found that incredibly erotic. I lifted my head up and sucked her tits, tasting her milk and getting her very hot. Finally she told Karl to move and stuck my cock up her ass. Karl, feeling left out, moved behind me and started licking my ass. I told him to get a condom on and give my ass what it needed. He smiled and, in a flash, he was balls-deep in my butt.
We fucked and sucked each other in several positions until Karl gave me a deep kiss, then left to join two guys who were fucking a pretty brunette. I last saw him sticking his cock up one of the guys' ass. Susie asked if I would like to play with her and another woman for a while. I quickly agreed and she said she would bring her over. She told me that the woman had gone through a nasty, protracted divorce which was finalized recently and she was sowing her wild oats and would love to have sex with a shemale. I went to get a drink and felt a hand on my shoulder. I turned and it was Susie and standing beside her was none other than Carol (Dannie's mother and Howard's wife) who had caught Howard and me on the pool table. I braced myself for a major scene, but instead she said "Hello Tess, Susie tells me that you are quite the little sex machine. Would you like to party with us for a while?" It suddenly occurred to me that she didn't recognize me. I knew the changes were significant, but this was proof that my transformation was complete.
Carol was a sexy woman - not in Jane's league - but pretty and shapely. I followed then to a semi-private alcove with a long, wide, upholstered bench about the size of a twin bed, but a bit longer. Susie had Carol and I lay on our backs with our heads at opposite ends. She then inserted a double-headed dildo in my ass and Carol's pussy. We then moved closer until our asses were almost touching. I must have had 10 inches in my ass and she had about 7 inches in her cunt. We scissored each other and began to fuck each other with the dildo. I couldn't help but remember the time I had done the same thing with her husband. Susie straddled my face and started rubbing her hot pussy on my tongue, then leaned over and licked my balls and Carol's cunt as we rocked against each other. After Susie and Carol came (I almost drowned), we shifted and Carol fucked Susie's pussy with a strap-on while I fucked Susie's ass. Then I fucked Carol's pussy while they 69ed. When I came, Carol sucked my cock and shared my cum with Susie. About that time, another guy walked by and Susie passed some cum on to him with a big kiss. It was wild to see a total stranger tasting my cum that way. He introduced himself simply as the Cockmaster. Susie whispered in my ear that he really deserved the title. Carol excused herself and joined another twosome, licking some blonde's pussy. Cockmaster certainly had impressive equipment - a gorgeous dick, about 8.5" long and thick. Cockmaster sat down and began sucking my cock, then we shifted into a 69. Suddenly, I felt a knock at my backdoor and felt Susie penetrate me with the strap-on. "I'm getting you ready for his big dick." she said smiling mischievously. Finally, his cock was fully erect and he asked if he could fuck my ass. I didn't respond except to push him on his back and mount that big fella. It was so thick that I had to work it in slowly. Eventually, I was resting against his pubic hairs with that big monster stretching my sphincter to its limits.
I started to rock on it when Susie straddled his torso and planted her ass on my cock. I was a bit awkward at first, but we worked out a rhythm. Cockmaster put a pillow under his head so he could lick her pussy as she rode my log and I rode his. Susie came two more times and slipped off before I shot a load on his chest. She leaned over and licked up my cum, again sharing it with Cockmaster. That really got him hot and he bucked my ass hard. He picked me up, still perched on his rod and walked around the room pounding my asshole repeatedly. Susie followed us around as he introduced me to various people, still reaming my ass. It was very erotic. When he was ready to cum he went to the middle of the big room and shot a gallon of cum in my mouth. It was like a firehose and it ran all over my face and tits. He also shot a little on my dick. He then laid me on my back, and several people began licking his cum off of my body. One cute raven-haired beauty with big tits (Andrea) licked my cock clean and fingered my ass. Her boyfriend, Rusty inserted a finger alongside hers and together they fingerfucked me. My cock didn't respond quickly, so Rusty decided to fuck me instead. He raised my legs and buried his sweet cock in my butt. Meanwhile, Susie and Andrea got into a 69 right beside us. I reached out and stuck a finger in Andrea's cunt. It was surprisingly tight for a girl that hung out with a crowd full of big cocks. She moaned and started fucking herself on my finger. She finally told Susie to stick a finger in her pussy and told me to stick mine in her ass, which I gladly did. She almost broke my finger when she started bucking and writhing against it. Rusty was giving me a nice fucking. He really knew how to stimulate my ass by rubbing his cockhead against my prostate. I told him he could shoot in my mouth, but he wanted to fill the rubber in my ass. After he came, he removed the condom and poured his cum on Andrea's asshole. He then instructed me to lick it off. When my tongue, hit her asshole, she went nuts, groaning and writhing. Poor Susie was getting pummeled as she licked Andrea's cunthole. Finally, I slipped on a rubber and planted my cock in Andrea's amazing ass. I have never felt an asshole so tight, not even on an anal virgin, but she acted like it was nothing. She was pushing back harder than I was pushing forward. Rusty began eating Susie's pussy, taking her mind off the woman who was rubbing her face so hard with her cunt. Andrea's ass was like a wonderland of stimulation. She squeezed and milked me, changing angles and pushing back to meet my thrusts. I came much quicker than usual and squirted my load into Susie's mouth. Andrea came one more time, then rolled off, allowing Rusty to kiss Susie and get his share of my jizz. I lay on the floor hugging and kissing Andrea as we rubbed our sweaty breasts against each other. At the group's next party, I met two guys and they persuaded me to let them both fuck my ass simultaneously. Their cocks were both about six inches long and not tremendously thick so I agreed. It took some effort, but they finally got both dicks in and gave me a solid assfucking. After they finished and I ate their cum, the older one sucked my cock, followed by the younger one, who got my load. I was struck by the way they never touched one another. After we finished, they revealed that they were father and son. It seems that the father had suspected that the son was bisexual and brought him to Miami to one of the wild clubs. They both ended up sucking cock that night and the father had his answer. From then on they made regular trips to Miami and had sex with men and tgirls. This was their first attempt at a double anal scene and I was glad they chose me. It was exciting, especially when they alternated moving in and out. I became a regular at these parties until a big scandal erupted and we had to stop having them. Apparently, one of the women brought her 15 year old daughter (she looked 25) and let her join in the fun. I'm glad I didn't have sex with her, although those who did said that she was certainly no virgin. I saw her take on two guys in every possible combination, including getting her ass fucked. She also ate pussy twice, including her mother's.
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).