0 comments/ 43828 views/ 3 favorites Case of the Jealous Transsexual Ch. 01 By: Jae_one_01 I met her on a free amateur’s web site. I have to admit that I was not particularly looking for a transsexual at the time. I had posted some naked pictures of myself on the site and had been going through the tons of emails that I had gotten in response when I ran across Dee as she called herself. She had sent me a picture and a simple email stating that she lived in the area. The picture didn’t show her face, nor did it show her penis. It was a picture of her bent of, her ass facing me. A nice ass, thick, even toned. I had contacted her through the AOL messenger service and we learned a little of each other for about a week before moving to the phone. She had the sexiest voice ever. There was no indication whatsoever of her being a transsexual. She had described herself as standing 5’6, 160, plump, thick, nice pussy, 36 b cup breast with big dark nipples. Dark chocolate complexion, medium length hair, full soft lips, and sexy eyes. I must admit after meeting her, the description was pretty close to the truth. We had never really made any plans on meeting. It happened on the spur of the moment. We were on the phone and I asked her in a flirting manner if I could possibly stop by her place and finally meet her. She, to my surprise agreed. I remember her asking how long it would take me to get there. I still had to shower and dress. It was late, about 11 but I had worked out earlier that evening and had yet to freshen up. Well I told her it would take me about 30 minutes to get ready and 15 minutes to get to her place, and that I would call her on my way out of the door. I had skipped on the shower getting dressed, and called her. She picked up the phone, she said she was about to get in the shower. I told her not to, that I’d like her to wait until I got there so we could shower together. She giggled and said yeah that it was a great idea. Then all over a sudden she took on a different tone. It really upset me when she said that she changed her mind, saying that she was not the type of female I was looking for. I really didn’t know what the hell she was talking about so I asked her “what kind of female are you then?”. That’s when she told me that she was a transsexual. She proceeded to explain that a transsexual is a man that feels that he is or changes himself into a woman, or vice versa. She added that she was a pre opt transsexual, meaning that she still had a penis that was fully functional, that her breast were real, she has not has any surgery of any kind, just hormone treatment which is why her voice was so feminine. After telling me the truth, she was happy to hear that I did not mind at all, that I had been with transsexuals in the past, and that they turned me on, and yes I still wanted to meet her. I took a cab to her place. I didn’t want to drive because she mentioned that she had drinks at the place and I didn’t want the burden of driving home drunk, in case I didn’t spend the night there, which I did not. I arrived at her apartment with some Chinese food; she mentioned on the phone that she was hungry. Her studio apartment was very cozy. She had really set the mood for a sensual evening. The place was dimly lit with candles all over. The temperature was perfect. She had a straight porno tape showing on a large screen television. A black couple was going at it strong. She complimented me on my looks even though she had seen a picture of me already via email; she said I looked even better in person. She took my coat and invited me to sit down on her couch. I sat and she brought me a shot of Hennessy and a bottle of Heineken. She also fixed me a plate of the food I had brought over. We made small talk while eating. The food was good and it gave us time to get a little bit more comfortable. She had decided on showering before I had gotten there, but I was still sweaty from my earlier workout. I told her that I still needed to shower and she said it was fine; she would get me some towels. As she got up to put away the dirty dishes she knelt in front of me and began to undo my pants, she pulled down my zipper and undid my belt. I raised my ass a little so that she could slide my pants and boxers down. She took the hint and my pants were down to my ankles before I knew it, and my semi hard dick was in her mouth. She was showing me why her AOL screen name was “blkoraldr” or something like that. I’m not quite sure. Well anyhow my dick grew in her mouth to its full 8 ½ inches. She slurped as she sucked like a vacuum. She rubbed my inner thigh and followed with long lick from my thighs to my balls, all this as she stroked my dick. She sucked each of my balls, gently, one by one, and licked the area right before my ass hole. Her mouth was so warm. She kept this up for about 20 minutes. During this time she would not let me use my hands to do anything. I tried touching her, caressing her face, grabbing her head, reaching for her breast, but she stopped ever attempt and asked me to just sit there and enjoy myself. It didn’t take me long to accept her request, especially the way she sucked on the tip and licked the hole so gently. She expertly stopped me from coming about 5 times, each time switching up the stroke so as to raise the great sensation I would feel from this orgasm. By this time I she had taken my shirt of as well and played with my nipples with her hands and tongue. She gave me sweet kisses and licks on my neck and ears. She licked my eyebrows, and kissed my eyelids and she kept a stroke on my penis with her hands. She licked down my chest back down to my balls and up my shaft. “Look at me” she said. When I looked down I could see the whites of her eyes looking up at me as she sucked on my dick ferociously. Up and down, in and out of her mouth. I knew this time she would not stop me from unloading in her mouth. She felt me tighten up and began to rub my asshole with a wet finger. I could feel the cum making its way up my shaft and so did she. She kept with the same even paced mouth stroke. Just as she heard me moan out loud that I was coming she stuck her index finger half way up my ass hole, and braced herself for my load. It shot straight to the back of her throat. I know because it made her gag for a half second. She somehow made the adjustment and was able to swallow every last drop. It was the first time my orgasm had gotten to that level of intensity. I was shaking like when a woman does when she has a great orgasm. Dee-Dee kept sucking me dry as I calmed down. When she was done she took a swig of beer and told me to go ahead and shower. I was so relaxed in the shower. The water was a perfect 80 degrees; she even had the very same brand of soap that I use. I took about 15 minutes in the shower. When I came out she invited me lay down in her bed, and she herself went in the bathroom for a few moments. Dee-Dee joined me in the bed. She was naked as I was. Before she lay down with me I told her to stand so I could get a look at her body. She had not missed a beat in her description, except for the 5 inch penis sticking out at me, inviting me to take it in my mouth and reciprocate what had been done to me so well. I grabbed Dee-Dee by her penis and pulled her towards me in the bed. She lay down and we started kissing. Her lips were so soft. This time I whispered for her to just lay there as I took my time exploring her body. Her skin was so soft and sweet. I kissed her all over; I sucked on her nice breast. She moaned every time I went near them so I always made sure that they were being stimulated at all times. When I finally got to her fully hard dick I took it all in my mouth. I had deep throated a dick at least as big as mine on more than one occasion so 5 inches was nothing. As I sucked her she moaned even louder and I felt her hand squeezing tightly on top of my hand, the one holding on to her breast. I sucked her just enough to get her really hot, even though she was as hot as she could ever get by this time. I licked down to her balls and pushed her legs up to get at her asshole to eat her out. I licked her sweet ass hole until I felt it was good and ready for my hard pole. I put on a condom and Dee-Dee surprised me once again. She told me she wanted to start out on top. She had a bottle of this great lubrication. She lubed herself and poured a little bit on me also. I lay on my back as she straddled herself on to my dick. She took her time sliding all 8 and ½ inches into her deep ass hole. When it was all the way in she increased the speed of the stroke. I grabbed on to her hips and guided her as she rode me. She would lean back and massage my balls as I squeezed on her tits. I was in heaven, Dee-Dee felt so good. This was definitely the best piece of ass I had ever gotten. Although I enjoyed the way she was riding me, it was time for me to take control of the situation. I told Dee-Dee to get up so that I could fuck her doggy style. She obliged by getting on all fours at the edge of the bed. I stood, feet on the floor, behind her and entered her once again. I had told her to arch her back and put her face to the pillow. I grabbed her hips as I guided myself into her tight ass hole. Once fully in, I started my long stroke motion. At a even pace I fucked Dee-Dee with long strokes, in and out, in and out as she moaned and begged for. As I got more and more into it, my pace increased. Within 10 minutes I was banging the hell out of her. I know that the next door neighbors had to be listening to us by this time. It would not have been hard, Dee-Dee was yelling to the top of her lungs. Fuck me, Fuck me!! Oh yes Daddy fuck me!! I wanted to see her facial expression as I fucked the life out of her so I made her turn around on her back. I pushed her legs back, as far as I could and entered her once more. This time I really got into her the way I wanted to. She tried pushing me back, but I persisted and she just gave in. I could see the tears coming from her eyes, and the lost look of extreme ecstasy on her face. As I continued to fuck her a shot of cum came streaming out of her penis. This was without any direct stimulation of any kind. She just came and it landed all over her nice tits, and some got on her lips, which she licked and swallowed. The rest she ate off of my fingers like some Halloween candy. Dee-Dee was the best. I wanted so much to cum in her that I took the condom off right before I was going to cum and unloaded my second one deep in her rectum. She held me as tight as she could, feeling my dick pulsating in her ass. As I pulled out she tightened so as to squeeze out any remaining cum. I know you’re wondering where the jealousy comes in… Well I first had to tell you how Dee-Dee and I met. Next I will let you in on our 3rd encounter. See the second was pretty much the same. But the third time I saw Dee-Dee she invited me over to meet her cousin from Florida, Alexis. She told me Alexis wanted to have a 3-some but it didn’t quite turn out that way… And so the jealousy took over. Stay tuned for part 2. Case of the Jealous Transsexual Ch. 02 ***If you've not read part one, please do so. It sets the tone for this story and you will understand exactly what is going on. *** Dee-Dee was becoming a little possessive after the 2 times that we had seen each other. She began calling me everyday, emailing me, wanting to know when will we see each other again and so on. To tell you the truth I had moved on. I had done everything with Dee-Dee that I felt could be done on a physical level and there was no where else to go. I needed a new experience and so I was not too interested in seeing her again. One late afternoon I had gotten a call on my cellular phone. The caller ID display read "private number." I normally do not pick up on "private numbers" but went against my rule that time. I pick up the phone sounding angry, "who is this?" I asked. "Damn baby don't be mad it's me Dee-Dee, just wanted to know where you are and what are you doing." I told her that I was busy but still inquired as to what she wanted. "Well" she said, "My best friend is here from Florida and she want to have a 3-some. She asked me to call the best dick I know and that yours baby, I want you to come and show her your work. She a tranny too, so what's up baby, are you up for a threesome tonight?" She had me there. Who would say no to that? I had already told her that I was busy even though I was not. So I told her that I would be done in a few hours and I would call her on my way there. I was home when I spoke Dee-Dee, so I took a shower and prepared myself for a great evening. Dee-Dee had told me that Alexis, her friend, had a show to do later that night. That I should hurry because she had to be prepared to go by 10pm. I was only 6, so that left plenty of time for fun. I got to Dee-Dee's at 6:30. Again the apartment was candle lit. There was a porno movie playing, and some soft music in the back round. Alexis was lying on the couch half sleeping and half watching the movie. I had not yet gotten a good look at her. Dee-Dee was smoking a cigarette when I walked in; she looked her usual sexy self. I sat on the couch at Alexis' feet. Her toes were pretty, looked as if she had just gotten a pedicure. They gave way to the prettiest legs ever. Nice toned calves, smooth chocolate colored skin... Alexis smiled and introduced herself, she extended a hand and I kissed it. "Oooohhh," she said, "a man with class, I like that." She gave me the widest smile and winked her eye, "nice to meet you too." Meanwhile Dee-Dee was in a hurry to get things started. She came over to me, hiked up her skirt. She opened up my zipper and started sucking me off, and then she stood up and grabbed a bottle of lubrication. She rolled a condom on my dick with her mouth and straddled me on the couch. She was riding me; definitely her favorite position. As she rode me like a while cowboy or should I say cowgirl, she whispered to me to get Alexis involved. Following orders I began to massage her leg, making my way up to her thighs. Alexis pushed my hand away "oh no Hun, you're busy right now," with that she gets up and moves to the bed. Now mind you we are in a small studio. So going over to the bed didn't make much of a difference but she was now out of reach. When Dee-De got up to walk to the bed I got a better look at her. She looked like she was picked out of a transsexual porn website. Her body was perfect. She had 38d chest, a coke bottle figure, the most passable face, she was just incredible. I could not believe my eyes. I could not take my stare off her. I watched her every move, even as Dee-Dee was riding away like a mad woman. As Dee-Dee slowed the pace down, Alexis noticed me watching her. I was watching her watch me. I never took my eyes off her I as I started to get more into Dee-Dee. I grabbed the back of Dee-Dee's hair and cupped one of her breast with my other hand. As she pushed down into me, I thrust myself up to meet her. My dick was all the way up her ass. She was screaming in delight. A lot of it was exaggerated, but I could tell Alexis was enjoying the show. About 15 minutes into it, Dee-Dee needed a break and went into the bathroom. I asked Alexis how come she would not join us. Her reply was "I don't do threesomes baby. And I'm tempted because you are one sexy mother fucker, but no love, no threesomes here. We can get together some other time though, one on one, just me and you." I was not too convinced; its not that she didn't sound sincere in what she said, I just could not leave that place without fucking Alexis. I asked her if I could at least see her full body without the silk robe on. She obliged. WOW!!! I could not believe my eyes. This was a definite fantasy in front of me. Her dick was a good 9 and ½ inches, her breast (although silicon) were perfect. Her skin was flawless. I was infatuated. I stood up from the couch and walked over to her. She looked at me and smiled. I just walked around her, admiring her. I touched her as if she were a work of art that I was afraid to damage. She closed her eyes as I got closer to her. I was inhaling her scent of perfume, my hands feeling her body how a blind man would do. The sensuality overcame us both and we embraced in a deep slow tongue kiss. We were eye to eye; Alexis stood at 5'10 and was maybe 155 lbs. Her body showed results from hard days at the gym. Flat stomach, six pack, tone biceps and triceps, defined back. Again, she was perfect. As we kissed she began to undress me, taking my shirt off, my pants and boxers, sock, everything. We stood naked flesh to flesh, kissing and caressing as if we were the only 2 people in the room. You see I was deep into Alexis that I forgot about Dee-Dee. She had been watching us from the couch the whole time. The phone ran, bringing me back to reality. Dee-Dee picked it up and lay in her bed. I then pulled Alexis over to the couch where we got comfortable and continued where we were interrupted. I lay on top of her and I could feel Dee-Dee's eyes burning a hole in my back but I didn't care, Alexis was my main concern. We kissed again slow, passionately. Our bodies exchanging heat, our hard dicks rubbing against each other, our every move was in synch. I wanted to feel my dick in her mouth, wanted to know how her tongue would treat it. I slid my dick across her stomach and up to her nipples where I rubbed it along and played there a little, then up her neck and into her welcoming mouth. Every once and while I would turn to see Dee-Dee's angry face looking along. This time when I looked she turn her back to me and covered her face with the sheets, she also turned the volume up on the stereo to drown out the moans. Alexis had all 8 an ½ inches of my dick in her mouth. I could feel her tonsils against the head. As she took it all in, I would feel her tongue tickling my balls, it was the best sensation, and she was definitely an expert. I had never felt such pleasure from a blow job. I began to tremble as she increased the speed. Her mouth was extremely wet; I felt her spit dribbling down my balls. It felt like a warm pussy. I got so into the feeling that I grabbed the back of her head and began to violently fuck her mouth. Her mouth was so wet that you heard squishing sounds, even with the loud music. God I wanted to cum, but I was no where close. I kept fucking Alexis' mouth harder and harder and she rolled with it. Noticing that I would not be cumin fast, she started playing with my balls, massaging them softly. She also slid a wet finger to my asshole, but not in it. Just over it, rubbing it, not hard and not soft, just enough to give me that wonderful sensation. I felt it! She could feel it too. Her finger started making it's way up my ass hole. The grip on my balls felt tighter, she was grabbing with pressure. I was thrusting in and out of her mouth faster and faster, the whole time never letting go of her head. Oh God I felt it, there it was... "I'm cumin! I'm cumin! YES!!!!! Aaaaaarrrrrrrrhhhhhggggggggggg!!!!!!!!!!!!" I let out the loudest scream as I came down her throat, her finger at my prostate, her right hand clutching my balls, and her mouth sucking me up... My legs almost gave out. Meanwhile Dee-Dee was still upset... Had she been truthful about the situation, about the 3-some that is, things would have been so much better. I noticed that while I was getting the best blow ever, Alexis' hard cock had filled up with blood and was ready to explode. Had Dee-Dee not been green with envy she should have come and sucked Alex off while I was fucking her face. Now that would have made for a 3-some! I had to lie down after that great orgasm. I lay on top of Alexis. I started stroking her cock against my own, and started getting hard again. I was spent but I was still horny. I would have stayed horny until I got to stick my dick deep in Alexis' round sweet ass. She turned to her side and I lay in back of her. I lifted her leg up and slid down so I could lick her ass out... I was fully hard by then and could not wait another minute. I placed the condom on and got the lubrication that Dee-Dee had used earlier. After applying a good amount on Alexis I pressed the head of my dick against her warm hole and began to fuck her slowly. I whispered little stupid things to her as we fucked, she loved it. She reached back to grab the back of my neck and pulled me towards her in a deep kiss. She smiled and kissed me again. I was working my 8 and ½ inches into her slowly. Enjoying the warmth and tightness, I was in ultimate ecstasy and Alexis knew it. So did Dee-Dee. As we kept on fucking my stroke got faster. At this point Alexis was in a doggy style position hanging over the back of the couch and I was standing behind her pounding away. I had not cum yet and she was getting very sore so she asked that I stop. I obliged, but lord knows I wanted to keep going. She said she just needed a small break. She had not had sex like this in a long time and I was tearing her up. While Alexis walked to the bathroom I went into the kitchen and got something to drink. I was sweating, and thirsty. After getting a cold glass of water I walked over to Dee-Dee. She was lying on the bed jerking off to the porno, well at least that's what she said but I knew she was jerking off to Alexis and I. As I approached her she rolled her eyes and gave me a look as if to say, "What do you want"? I asked if she was upset and she said no. "You went after what you wanted, I can't be mad at you," she said in a very sarcastic tone. I had to remind her that she was the one that invited me over specifically to fuck her friend, and she also was the on that suggested that I make a move on Alexis. "I said I'm not mad!" she yelled at me, "move out the way you're blocking the movie." I moved out of her way and sat next to her on the bed. I started sucking on her tits but she pushed me away. "Get the fuck off me" she started, but stopped when she heard Alexis coming out of the bathroom. Both Dee-Dee and I got off the bed at the same time, I went into the bathroom and she into the kitchen. When I came out and the two women had switched places. Alexis was lying in the bed and Dee-Dee on the couch, still masturbating to the same movie. My dick was still hard I still had some unfinished business with Alexis so I got in the bed with her. Alexis moved over until she lay in the middle of the queen sized mattress. I lay on top of her and started stroking her large dick. She was bigger than me and I'm not small! Her dick was like a straight arrow, a sharp contrast to my curved one. It was thick and circumcised. I kissed her breast as I kept on stroking her dick, kissing down to her stomach until I put the head of her dick in between my lips. I started with a slow suck, just the head, and worked my way down her shaft up and down. She was really enjoying it. Her hand was rubbing my head, her breathing getting heavier, and her hips coming up to meet my lips in a rhythmic motion. I cupped and massaged her balls at the same time. I could smell the fresh soap. She had just washed up in the bathroom, I licked her all over, her soft thighs, the back of her knee- which made her laugh- she had never experienced soft kisses at the back of her knee. I tongue kissed the head of her penis, truly enjoying the moment; savoring her flavor... she tasted so sweet. She pulled me up to her lips in a deep kiss, at the same time she reached for a condom. I though she was ready to get fucked again but to my surprise she started putting the condom on herself; she wanted to fuck me. I've never been entered anally by anything bigger than her long middle finger and I had not the intention of doing so that night. She was disappointed when I told her that I was not interested in getting fucked. I guess rubbing her dick on my ass hole sent her crossed signals, but I just like the sensation and eroticism of the act. I wanted to fuck her but her ass hole was too sore. We both lay there wondering what we were going to and as if at the same time we both looked over at Dee-Dee. Alexis and I played rock-paper-scissor to see who was going to fuck Dee-Dee first, she won. The trick was to get Dee-Dee off that couch, it wasn't hard. We told Dee-Dee to come join us because we were done; that she is the one that set up the little get together and was being a bad host. After a little bit of persuading she came over, naked, and got in the bed with us. Alexis began sucking on her tits as soon as Dee-Dee hit the mattress. Dee-Dee was on her back in no time with her legs up. I grabbed the lubrication poured some on the tip of Alexis' dick and she roughly entered Dee-Dee. Dee-Dee screamed from the sharp pain, even though she was used to anal sex, Alexis had a large tool and it seemed like it would be hard for anyone to handle. As Alexis pounded away at Dee-Dee I initially started fucking her mouth. It was difficult for Dee-Dee to give me a good blow job because of the force at which Alexis was fucking her. Instead I just stroked myself as I watched the show. Fifteen minutes later Alexis still had not cum, and I was in dire need to join in the action. I noticed that Dee-Dee's 5 inch dick was to its peek. I made Alexis stop what she was doing and had her start riding Dee-Dee. I took position where Alexis was, and entered Dee-Dee with ease. Alexis had Dee-Dee's hole nice and lubed up, but Dee-Dee still managed to squeeze down on my shaft as I entered her. With both women facing me I fucked Dee-Dee and kissed Alexis as she rode Dee-Dee's hard dick. I was close to coming and as I stroked Alexis I could feel her dick swelling up and becoming hot with the heat from the traveling sperm about to erupt. Dee-Dee herself was very close to orgasm... It was the best cum shot never caught on tape. As I pulled out to shoot my load, Dee-Dee pulled out from underneath Alexis and shot her load in the air, right in between us. Her cum shot high and I caught some with my hand on the way down, I stuck that very hand in Alexis' mouth just as my own sperm shot up to her gigantic tits and she was rubbing every drop as if it was the "lotion of youth." Not too long after, I mean less then 30 seconds, it was Alexis turn to shoot the heaviest load of all right onto my dick and balls, her sperm was so warm, I grabbed her dick to squeezed out every last drop; I was spent and lay back on the bed stroking my cum covered dick, and as I lay there I felt Dee-Dee's tongue lapping away at my balls, cleaning up the mess Alexis had left behind. Even though we had a great time Dee-Dee was still upset afterwards. I guess it didn't help when I fell asleep with Alexis lying on my stomach with my semi hard dick in her mouth. I asked Dee-Dee to join us but she refused. She went over to the couch and slept like a baby. In the morning, she fixed breakfast for two... Alexis shared her food with me, and we had another round of hot sex in the shower before I left. Alexis left for Florida the next day. We've spoken on the phone a few times since then; I'm to visit her the next time I'm there on business. Stay tuned for the episode, should make a great story.