Hi, my name is Jennifer and I am a sissy, but I wasn’t always that way. My story is 100% true, but I wish some parts of it weren’t. I grew up in a very dysfunctional home. My parents were physically and verbally abusive. They divorced in 1985 and both of them ended up moving to Maryland. My mom started dating Black men. She would bring them home, and they would smirk at me, as my mom led them up the stairs to her bedroom to get fucked. She was very loud, and I would listen to her getting fucked and jack off.
I had two best friends in middle school, one was Black and the other was white and gay. We were like three peas in a pod, inseparable, but I never thought about either of them in a sexual way. The closest we ever got to doing anything sexual was jacking off together, when we were at our gay friend’s house for a sleepover. We all ended up going to high school for the first two years, and they were my escape from my family. Their parents were everything I wanted but never had. In my junior year, my mom transferred me to public school. I made a few friends, but none were ever like my best friends.
Sometimes my mom would leave and go to her studs’ homes for a week or two at a time, leaving me by myself. One time, after she had left, I decided to wear her underwear, wig, slutty clothes and high heels. Then I put some makeup on and looked at myself in the mirror, and what I saw aroused me. I went to her nightstand, took her Black dildo out and fucked myself with it. I came within a minute. I was 16 and the seed of what I wanted to be was planted, but the society in which I grew up looked down on gay people, so I suppressed my desires, ashamed of myself.
I realized in my senior year that I didn’t want to go to college. It just so happened that in January of 1991 Desert Storm started, so I decided to do what society deemed “normal” and enlisted in the National Guard the next day. A month and a half later, it was all over, but I was still leaving for boot camp. As it turned out, I had to go to summer school to learn how to type, because one of my classes from private school didn’t transfer over to public school.
While I was in summer school, my mom decided that she didn’t want me around anymore, so she kicked me out of her house on my 18th birthday. I wasn’t due to leave for boot camp for another four months, and so I was homeless. I bounced around from one friend’s house to another, until my Squad Leader felt sorry for me and let me crash on her sofa. As it turned out, she was into Black men too and brought home a different guy every night. The seed in mind resurfaced and I jacked off, while she would get fucked.
I graduated from boot camp in early 1992 and was then stationed in Monterey, CA for my follow-on school, which lasted a year and a half. I was 5’11” and 135lbs, very slender build and almost no body hair whatsoever, not even in my pubic area. What light fuzz I had was on my arms. I became friends with a girl named Heather who was three years older than me and she became a big sister to me. We did everything together, and for the first time I was happy. I truly loved her. We are still friends to this day.
One Friday night we went into downtown Monterey to a pub. Since she was old enough, Heather ordered drinks for us and I got pretty *******. I don’t remember how we got back to the barracks, but I couldn’t find my room key, so I ended up crashing on the sofa in our day room. She tucked me in with a blanket and pillow. I couldn’t stay in her room, because it was against regulations and we didn’t want to get into trouble.
I quickly fell asleep, ******* is probably a better term, but I was still kind of aware of a door opening. My neighbor from down the hall, Chris, was a very attractive Black man, 6’5” and 225lbs of pure muscle, and he came out into the day room, woke me up and told me I could crash in his room, so I wouldn’t be uncomfortable on the sofa. I stumbled into his room and didn’t even comprehend that he was helping out of my clothes and into his bed. I fell right back asleep. He got into bed with me and spooned me.
My eyes opened up instantly, when I felt something pressing on my ass, but I was too frozen with fear to react. Chris had taken some lube and put it in my ass with his finger, making sure to get my ass crack nice and lubed. I wanted to scream but I couldn’t, because I was afraid he might beat the hell out of me if I did. Besides that, he had me blocked in on the bed, against the wall, so I had nowhere to go.
Right after Chris lubed my ass, I felt an incredible pressure against it. Then I felt a burning sensation and saw stars. I had never seen his cock, but I could feel that it was big. Again, even though it hurt like hell, I pretended to still be *******. Chris actually took his time and once he was all the way in, he stayed like that for about a minute or two, then he started pumping my ass.
I don’t know how long he fucked me, but it felt like it was all night. After a while I heard him breathing heavier then he thrust into me pretty hard and I felt him cumming inside me…..I felt his warm seed flooding my guts, and at that point I really wanted to freak out.
The only thing that calmed me down was the fact that the military tests for HIV, so I rationalized that Chris was clean and I would be okay. But now the realization set in that a rather large Black man had just taken my anal virginity and planted his seed in me. I felt shame and humiliation and silently cried myself back to sleep. Chris fell asleep with his cock still inside me.
I woke up on Saturday to Chris’ hard cock fucking me again and this time there was no pretending that I was *******. I shot forward to the wall and flipped around yelling, “What the hell are you doing?????” Chris looked at me with a smile and said, “You didn’t complain last night, and don’t even try to tell me you were *******, because I know you weren’t”. I could feel my face turning red with embarrassment and the words, “Please don’t tell anyone” came out of my mouth. Chris smiled again and said, “If you don’t want anyone to know that you’re a little faggot, you’re going to let me tap that ass whenever I want.
I started crying again, because I didn’t want anyone finding out what had happened…the military wasn’t very kind to that sort of thing, but I never stopped to think that Chris would have gotten into trouble too. I nodded, resigning myself to the fact that I now belonged to a Black man. It was humiliating, but at the same time I was incredibly aroused. Chris told me to flip onto my stomach and spread my legs. I did as I was told and then he put a pillow under my hips. He then mounted me and sank his cock right into my ass, with no effort whatsoever. The cum he had deposited in me the night before was still inside me and provided the lubrication. We didn’t leave his bedroom all weekend and he fucked me damn-near non-stop. He could get hard and start fucking within five minutes of cumming.
Chris had me come to his room every night. I had a roommate, so coming to my room was out of the question, but Chris had no roommate. The first couple of nights he fucked me as he had the first weekend but one night, when I went into his room, he told me to get on my knees. I did as I was told, and he pulled his cock out.
I had never really gotten a good look at his cock, but knew it was big. I just never realized, until it was an inch from my face, just how big his cock was. I never measured it but it went from the tip of my fingers to a little bit past my wrist, and it was thick. Chris told me to open my mouth and when I did he rammed his cock to my throat. I’ve never had a gag reflex, so I think I surprised him, when I deepthroated him. The only thing that made me pull away was when I ran out of air.
Chris face fucked me for quite a while and then he told me to lay on the bed and tied wrists to the bed posts. He lifted my legs and tied them to the same bed posts as my wrists, leaving my ass at his disposal and he fucked me again for several hours, cumming multiple times. I had to start doing Kegel exercises, to keep my ass from getting too loose.
A couple of weeks passed and Chris told me to put in a request to change rooms, using the excuse that my roommate snored. As his was the only room with available space, my request was approved and I moved in with Chris. He now had full control over me, including what I ate. Per his demand, I became a vegan, so I could maintain my slender figure, and he had me do a lot of squats every night, so that I would have a nice bubble butt and other exercises that gave my hips a more feminine look. He fucked me every single night and we never left the room on weekends. I was now looking forward to feeling his cock inside me.
One day after school Chris told me go to Victoria’s Secret and buy sexy underwear, and then I was to go to Macy’s and pick out a girly outfit and shoes and get some makeup. He also wanted me to get a pedicure and ask for hot pink color. I was embarrassed, when I walked into the store, but the sales girl was very nice and never once judged me. I picked out thongs, lace bikinis, string bikinis along with some bras and silicone breast enhancing inserts. Then I went to Macy’s and found a short skirt, the kind that Catholic schoolgirls wear, and nice halter top to go with it. A pair of five inch heels rounded out the outfit.
The shoe lady looked at me weird, but I made up an excuse that I was buying them for my girlfriend and we had the same shoe size. I wasn’t worried about walking in them, because I had learned how to walk my mom’s stilettos. I then found makeup colors that I thought would look slutty. When all was said and done, I spent over $500, but I felt sexy walking out of there, and I couldn’t wait to try everything on for Chris.
I made my final stop at the nail salon and sheepishly told the nail tech that I had lost a bet with my buddy, and this was my punishment. She laughed and said that white boys were silly. I had never had a pedicure before, but I can tell you that I haven’t gone without once since. My toes were so cute, when she was done putting the hot pink on them. I also bought a bottle of polish and some nail polish remover, so I could do my fingernails every evening. Again, the military frowns on that, so I had to look like I was “normal”. Chris fucked me harder than he ever did that night and I’m pretty sure he came even more too.
Per his orders, I had to ditch all of my boy underwear, putting them in his drawer, in case of an inspection, and I had to start wearing my girl underwear every day, even in uniform. I always got out of class before Chris and would get back to our room first. I would be out of my uniform, ass in the air with my panties on for him, by the time he walked in. He always had a smile, when he walked in.
Chris started to seem genuinely caring towards me and even began kissing me, when he was inside me. He had full lips and they were heaven to kiss. What started out as him fucking me turned into us making love, and I told him I loved one night after he had shot a massive load in me. He smiled and told me he loved me too.
We started going to San Francisco on the weekend. On our first trip up there, we got a hotel room, dropped our stuff off and went directly to an adult store. Chris wanted me to get a wig and a chastity cage. I had a habit of touching my little dick, when he fucked me. He told me in no uncertain terms that I was to start referring to my dick as a clit and my ass was now a pussy or cunt. I picked out a wig like the one that Kathleen Turner had as China Blue in “Crimes of Passion”.
The chastity cage took a bit more deciding. There were so many models to choose from, but in the end, I found a stainless steel cage that was really small and would lock my clit in place but allow me to wash without having to take it off. When we got back to the hotel, Chris told me to jack off in front of him. He had never asked me to do this, but I didn’t question him. It only took about a minute to cum, and barely anything came out.
When I got soft, Chris told me to put the chastity cage on. He told me that it would be easier, now that I couldn’t get a hard on for a while….it would take me hours to get hard after cumming. The hardest part was fitting my testicles through the small ring. It took some effort, but I got the ring on and then put the cage on. A barrel lock mated both pieces together. Once I was locked in, Chris told me to give him the keys.
He said that he was going to give them to Heather, because she knew that we had become an item and was very supportive of us. At the same time, she would get off on knowing that those keys were what was keeping me from touching myself. Chris then told me to get all dolled up, because we were going out to a bar for drinks. I never had a problem getting served, as long as I was with someone who was of age, so I took the time to make myself look like a hot little slut. Putting the panties over my clit cage felt a little weird, but at the same time it felt very sexy, because it put some pressure on that area, reminding me that it would always be there.
We walked to the bar, which was three blocks away. The five inch heels gave me no problems and I was still about an inch shorter than Chris. We didn’t even get carded, when Chris ordered our drinks, a Jack and Coke for himself and a Long Island Iced Tea for me. He wanted to make sure that I would be uninhibited enough for what he had planned later. We spent a couple of hours at the bar, and there were a lot of guys in there. I felt quite a few eyes on me, and it made me feel very uncomfortable yet it was a real ego boost to know that they wanted me.
What I hadn’t realized was that Chris had taken me to a gay bar, and when he went to the bar to order our drinks, he told as many people as he could that I was a sissy crossdresser. He told me that tidbit much later, and it became our regular spot, when we spent the weekend in town. I was on my second Long Island Iced Tea and really beginning to feel it, when a handsome Black man as big as Chris came to our table and started chatting with us. The more I sipped my *******, the more my head began to swim, and the more it seemed that this man, David, was flirting with me. I looked over at Chris, who was smiling. I smiled back, truly oblivious to what was going on.
When I finished my *******, Chris suggested we leave. I didn’t realize that “we” meant David was coming with us. I got up and couldn’t balance on my heels, so I took them off and walked barefoot. I was maybe 20 feet out of the bar, when I saw that David was walking with us. Like a bimbo, I asked him if he lived near where we were staying. He laughed and told me he was staying with us tonight. I was so tipsy that I just smiled and told Chris that it was nice of him to let him stay with us. They both laughed at the same time.
When we walked into our room, Chris told me to get on the bed and dance for them. I got up but the alcohol was preventing me from keeping my balance and I fell, but thankfully I didn’t fall off the bed. I was laying on my back, with my head hanging slightly off the foot of the bed, and I started giggling. I said, “Oh, the room is spinning!” and Chris and David laughed. I closed my eyes to try and stop the spinning but then I got nauseous, so I opened my mouth and started breathing deeply to make it go away. It was then that Chris shoved his cock into my mouth……so I thought. I opened my eyes but a set of balls was resting on them. Chris had big balls but they didn’t hang that low. Immediately I freaked out, realizing what was going on.
Chris jumped on the bed and pinned me down so I couldn’t move. He said, “Take it easy, baby. I wanted to give you a treat, because you looked so good that first day you wore your girl clothes for me, and I knew that sharing you would boost your ego.” Being ******* makes everything sound logical and I calmed down. David resumed fucking my mouth. His cock was bigger than Chris’ too, something I didn’t know was possible. We spent the entire weekend in the room, and they fucked me mercilessly. I lost count of how many loads I had in me, but I couldn’t hold them in…cum was just oozing out.
For Christmas of 1992 Chris and I both took two weeks of leave and decided to spend it in San Fran. Chris told me that he had a special Christmas gift for me, and the anticipation was killing me as we spent the two and a half hours driving. We got to our usual hotel and I immediately changed into my girl outfit. Chris had me wear my white lace bra and string panties. I kept pestering him about my Christmas gift, but he told me I had to wait.
Once I was dressed, he told me to get on the bed, on my stomach, with my head at the foot of the bed. I did as I was told. Chris gave me a silk black sleeping mask to put on and then he tied my wrists and ankles to the bedposts. Once he was satisfied that I couldn’t move, he told me he was going out to get my gift. I told him I couldn’t wait to get it, and he laughed. It was a laugh I knew and it made me a bit nervous.
Chris came back about two hours later, and I was mildly annoyed, because I hadn’t expected him to take as long as he did, but I knew better than to say anything. Early on in our “relationship” I had talked back to Chris and he slapped me so hard I saw stars. I never talked back again. One thing I noticed was that he wasn’t alone, because I heard multiple footsteps but no one was talking, which made me even more nervous, but I was immobile and couldn’t remove my mask to see what was going on.
“Hi baby, I’m back and I brought your gift. I’m going to put this bottle under your nose and I want you to inhale, until I tell you stop. When you do, I want you to hold your breath, until I tell you exhale. Do you understand?” “Yes, Sir, I understand.”
Chris held the bottle under my nose and told me to inhale deeply. It smelled a bit fruity to me, but there was a strong pungent aspect to it too. He then told me to hold my breath for what seemed like an eternity and then he told me to exhale. Almost immediately I felt my heart pounding and I immediately got horny as hell. My cock had long stopped having erections, but my pussy was pulsing and I wanted to get fucked.
He asked me how I felt, and I told him that I really wanted to get fucked and that he should call David to come over, because I really wanted cock. Chris laughed and said, “Well I’m glad you said that, because David is here, and so are five other guys. I wasn’t even panicked at all; hearing Chris say that just made me hornier. “Well don’t just stand there, fill my holes!” My transformation into a bimbo sissy slut was complete.
Chris kept giving hits of poppers all night, and I took cock after cock after cock for days on end. Cum was flowing out of me non-stop and no Kegel exercise in the world would have kept my pussy from stretching as much as it did. I was in heaven and I didn’t want our Christmas vacation to end but it had to. I sucked Chris’ cock all the way home and swallowed four loads. It’s a miracle I didn’t get HIV during those two weeks, because it would have probably killed me, considering Freddy Mercury had died of AIDS the year before, and meds to treat the disease weren’t what they are today, AND we were in the gay Mecca of the United States.
Chris graduated three months before I did. I was hoping that we would be stationed together, but I was going on to Arizona and then home; he went to Germany. He was gone before I got home from school. His stuff was gone and there was no goodbye note. I fell to the floor and started crying uncontrollably. I was mad and I couldn’t understand why he would just leave without saying a thing, after I had completely given myself to him. My girl-friend came into the room and sat down next to me, putting her arms around me.
She told me that Chris had knocked on her door and asked her to give me the keys to my chastity cage and that he wasn’t good with goodbyes, so he asked her to say goodbye to me for him. I couldn’t stop crying. She just kept hugging me and telling me to let it all out. After a half hour, I composed myself and felt stupid for crying so much. I asked Heather to give me the keys to my cage, so I could take the damn thing off and to my surprise she said, “Let’s keep it on a bit longer”. The submissive in me kicked in and instinctively said, “Yes, Mistress”. Heather laughed at my reply and said, “I love the sound of that! You just opened Pandora’s Box, Jenny!”….no one close to me called me by my boy name anymore. Heather told me to put a cold, damp cloth on my face, to reduce the puffiness in my eyes, and she was going to take me to dinner.
Once my eyes went back to normal, I got undressed. Heather had seen me naked a thousand times, so it didn’t bother either one of us in the slightest to see the other one without clothes. I went to my drawer to get my boy underwear out, and there wasn’t any. Chris had taken them all. I cussed. Heather laughed and explained that it was actually her idea for him to take them, because she wanted to keep me in the life to which I had become accustomed. She told me that she had decided that she was going to take over as my domme but that there would be zero traditional sex involved between us.
Instead, she was going fuck guys in front of me, and my job would be to clean them up, when they were done. I wasn’t sure about her idea and told her that I thought of her as a sister. She told me that she thought of me as a sister too, but this was non-negotiable and I would do as I was told or she would throw my chastity cage keys into Monterey Bay. I was incredibly turned on, but my clit had no response, so I reluctantly agreed. She finished by saying, “Besides, I hear you’re a great cocksucker, and I want to see if you’re better than me.” I smiled.
That part of our relationship was, I’ll admit weird for me. In fact, to this day we don’t speak of it, but she did give me back the keys to my cage, and I still have it.
As I got older, I married a woman, because I wanted to fit into society’s idea of “normal”. I tried to discretely share my proclivities with her, but she had no interest in it. She did use the black 8” dildo that I bought her, but then again, so did I. Several times during our marriage I got the urge to get fucked, so I created a profile on a gay hookup site to satisfy my cravings. We realized after 10 years that we had nothing in common, so we went our separate ways. I finished my career in the military and got fucked a few more times but continued to try to conform to society’s definition of “normal”.
I’m now 45 years old and realize that there is no such thing as normal. In fact, the last time I felt “normal” was when Chris and I were together and I was living as a girl full time. I felt normal with that chastity cage on my clit, and I felt normal when I had a Big Black Cock inside of me and being bred.
So, to end this diatribic monologue, I’ve decided that I’m going to transition into Jennifer full time and say goodbye to society’s version of “normal” me. My goal is to do this in stages, starting with hormones to get rid of the testosterone in my body and replacing it with estrogen. I want to do everything I can to grow natural breasts, so that I can get big silicone implants. I want to be castrated, because I never liked that annoying sack between my legs. I may or may not have my clit removed and turned into a man-made pussy.
I DO know for sure that I want someone to take control of me again and give me that secure, “normal” feeling again. I am not opposed at all to being a cuckold again. As weird as it was with Heather, I did enjoy the humiliation of being told I didn’t measure up to her bull and then being told to clean the cum out her and clean the bull’s cock. What I would really love, though, is to become a Black man’s property again and be his bimbo fuck slut forever.
I had two best friends in middle school, one was Black and the other was white and gay. We were like three peas in a pod, inseparable, but I never thought about either of them in a sexual way. The closest we ever got to doing anything sexual was jacking off together, when we were at our gay friend’s house for a sleepover. We all ended up going to high school for the first two years, and they were my escape from my family. Their parents were everything I wanted but never had. In my junior year, my mom transferred me to public school. I made a few friends, but none were ever like my best friends.
Sometimes my mom would leave and go to her studs’ homes for a week or two at a time, leaving me by myself. One time, after she had left, I decided to wear her underwear, wig, slutty clothes and high heels. Then I put some makeup on and looked at myself in the mirror, and what I saw aroused me. I went to her nightstand, took her Black dildo out and fucked myself with it. I came within a minute. I was 16 and the seed of what I wanted to be was planted, but the society in which I grew up looked down on gay people, so I suppressed my desires, ashamed of myself.
I realized in my senior year that I didn’t want to go to college. It just so happened that in January of 1991 Desert Storm started, so I decided to do what society deemed “normal” and enlisted in the National Guard the next day. A month and a half later, it was all over, but I was still leaving for boot camp. As it turned out, I had to go to summer school to learn how to type, because one of my classes from private school didn’t transfer over to public school.
While I was in summer school, my mom decided that she didn’t want me around anymore, so she kicked me out of her house on my 18th birthday. I wasn’t due to leave for boot camp for another four months, and so I was homeless. I bounced around from one friend’s house to another, until my Squad Leader felt sorry for me and let me crash on her sofa. As it turned out, she was into Black men too and brought home a different guy every night. The seed in mind resurfaced and I jacked off, while she would get fucked.
I graduated from boot camp in early 1992 and was then stationed in Monterey, CA for my follow-on school, which lasted a year and a half. I was 5’11” and 135lbs, very slender build and almost no body hair whatsoever, not even in my pubic area. What light fuzz I had was on my arms. I became friends with a girl named Heather who was three years older than me and she became a big sister to me. We did everything together, and for the first time I was happy. I truly loved her. We are still friends to this day.
One Friday night we went into downtown Monterey to a pub. Since she was old enough, Heather ordered drinks for us and I got pretty *******. I don’t remember how we got back to the barracks, but I couldn’t find my room key, so I ended up crashing on the sofa in our day room. She tucked me in with a blanket and pillow. I couldn’t stay in her room, because it was against regulations and we didn’t want to get into trouble.
I quickly fell asleep, ******* is probably a better term, but I was still kind of aware of a door opening. My neighbor from down the hall, Chris, was a very attractive Black man, 6’5” and 225lbs of pure muscle, and he came out into the day room, woke me up and told me I could crash in his room, so I wouldn’t be uncomfortable on the sofa. I stumbled into his room and didn’t even comprehend that he was helping out of my clothes and into his bed. I fell right back asleep. He got into bed with me and spooned me.
My eyes opened up instantly, when I felt something pressing on my ass, but I was too frozen with fear to react. Chris had taken some lube and put it in my ass with his finger, making sure to get my ass crack nice and lubed. I wanted to scream but I couldn’t, because I was afraid he might beat the hell out of me if I did. Besides that, he had me blocked in on the bed, against the wall, so I had nowhere to go.
Right after Chris lubed my ass, I felt an incredible pressure against it. Then I felt a burning sensation and saw stars. I had never seen his cock, but I could feel that it was big. Again, even though it hurt like hell, I pretended to still be *******. Chris actually took his time and once he was all the way in, he stayed like that for about a minute or two, then he started pumping my ass.
I don’t know how long he fucked me, but it felt like it was all night. After a while I heard him breathing heavier then he thrust into me pretty hard and I felt him cumming inside me…..I felt his warm seed flooding my guts, and at that point I really wanted to freak out.
The only thing that calmed me down was the fact that the military tests for HIV, so I rationalized that Chris was clean and I would be okay. But now the realization set in that a rather large Black man had just taken my anal virginity and planted his seed in me. I felt shame and humiliation and silently cried myself back to sleep. Chris fell asleep with his cock still inside me.
I woke up on Saturday to Chris’ hard cock fucking me again and this time there was no pretending that I was *******. I shot forward to the wall and flipped around yelling, “What the hell are you doing?????” Chris looked at me with a smile and said, “You didn’t complain last night, and don’t even try to tell me you were *******, because I know you weren’t”. I could feel my face turning red with embarrassment and the words, “Please don’t tell anyone” came out of my mouth. Chris smiled again and said, “If you don’t want anyone to know that you’re a little faggot, you’re going to let me tap that ass whenever I want.
I started crying again, because I didn’t want anyone finding out what had happened…the military wasn’t very kind to that sort of thing, but I never stopped to think that Chris would have gotten into trouble too. I nodded, resigning myself to the fact that I now belonged to a Black man. It was humiliating, but at the same time I was incredibly aroused. Chris told me to flip onto my stomach and spread my legs. I did as I was told and then he put a pillow under my hips. He then mounted me and sank his cock right into my ass, with no effort whatsoever. The cum he had deposited in me the night before was still inside me and provided the lubrication. We didn’t leave his bedroom all weekend and he fucked me damn-near non-stop. He could get hard and start fucking within five minutes of cumming.
Chris had me come to his room every night. I had a roommate, so coming to my room was out of the question, but Chris had no roommate. The first couple of nights he fucked me as he had the first weekend but one night, when I went into his room, he told me to get on my knees. I did as I was told, and he pulled his cock out.
I had never really gotten a good look at his cock, but knew it was big. I just never realized, until it was an inch from my face, just how big his cock was. I never measured it but it went from the tip of my fingers to a little bit past my wrist, and it was thick. Chris told me to open my mouth and when I did he rammed his cock to my throat. I’ve never had a gag reflex, so I think I surprised him, when I deepthroated him. The only thing that made me pull away was when I ran out of air.
Chris face fucked me for quite a while and then he told me to lay on the bed and tied wrists to the bed posts. He lifted my legs and tied them to the same bed posts as my wrists, leaving my ass at his disposal and he fucked me again for several hours, cumming multiple times. I had to start doing Kegel exercises, to keep my ass from getting too loose.
A couple of weeks passed and Chris told me to put in a request to change rooms, using the excuse that my roommate snored. As his was the only room with available space, my request was approved and I moved in with Chris. He now had full control over me, including what I ate. Per his demand, I became a vegan, so I could maintain my slender figure, and he had me do a lot of squats every night, so that I would have a nice bubble butt and other exercises that gave my hips a more feminine look. He fucked me every single night and we never left the room on weekends. I was now looking forward to feeling his cock inside me.
One day after school Chris told me go to Victoria’s Secret and buy sexy underwear, and then I was to go to Macy’s and pick out a girly outfit and shoes and get some makeup. He also wanted me to get a pedicure and ask for hot pink color. I was embarrassed, when I walked into the store, but the sales girl was very nice and never once judged me. I picked out thongs, lace bikinis, string bikinis along with some bras and silicone breast enhancing inserts. Then I went to Macy’s and found a short skirt, the kind that Catholic schoolgirls wear, and nice halter top to go with it. A pair of five inch heels rounded out the outfit.
The shoe lady looked at me weird, but I made up an excuse that I was buying them for my girlfriend and we had the same shoe size. I wasn’t worried about walking in them, because I had learned how to walk my mom’s stilettos. I then found makeup colors that I thought would look slutty. When all was said and done, I spent over $500, but I felt sexy walking out of there, and I couldn’t wait to try everything on for Chris.
I made my final stop at the nail salon and sheepishly told the nail tech that I had lost a bet with my buddy, and this was my punishment. She laughed and said that white boys were silly. I had never had a pedicure before, but I can tell you that I haven’t gone without once since. My toes were so cute, when she was done putting the hot pink on them. I also bought a bottle of polish and some nail polish remover, so I could do my fingernails every evening. Again, the military frowns on that, so I had to look like I was “normal”. Chris fucked me harder than he ever did that night and I’m pretty sure he came even more too.
Per his orders, I had to ditch all of my boy underwear, putting them in his drawer, in case of an inspection, and I had to start wearing my girl underwear every day, even in uniform. I always got out of class before Chris and would get back to our room first. I would be out of my uniform, ass in the air with my panties on for him, by the time he walked in. He always had a smile, when he walked in.
Chris started to seem genuinely caring towards me and even began kissing me, when he was inside me. He had full lips and they were heaven to kiss. What started out as him fucking me turned into us making love, and I told him I loved one night after he had shot a massive load in me. He smiled and told me he loved me too.
We started going to San Francisco on the weekend. On our first trip up there, we got a hotel room, dropped our stuff off and went directly to an adult store. Chris wanted me to get a wig and a chastity cage. I had a habit of touching my little dick, when he fucked me. He told me in no uncertain terms that I was to start referring to my dick as a clit and my ass was now a pussy or cunt. I picked out a wig like the one that Kathleen Turner had as China Blue in “Crimes of Passion”.
The chastity cage took a bit more deciding. There were so many models to choose from, but in the end, I found a stainless steel cage that was really small and would lock my clit in place but allow me to wash without having to take it off. When we got back to the hotel, Chris told me to jack off in front of him. He had never asked me to do this, but I didn’t question him. It only took about a minute to cum, and barely anything came out.
When I got soft, Chris told me to put the chastity cage on. He told me that it would be easier, now that I couldn’t get a hard on for a while….it would take me hours to get hard after cumming. The hardest part was fitting my testicles through the small ring. It took some effort, but I got the ring on and then put the cage on. A barrel lock mated both pieces together. Once I was locked in, Chris told me to give him the keys.
He said that he was going to give them to Heather, because she knew that we had become an item and was very supportive of us. At the same time, she would get off on knowing that those keys were what was keeping me from touching myself. Chris then told me to get all dolled up, because we were going out to a bar for drinks. I never had a problem getting served, as long as I was with someone who was of age, so I took the time to make myself look like a hot little slut. Putting the panties over my clit cage felt a little weird, but at the same time it felt very sexy, because it put some pressure on that area, reminding me that it would always be there.
We walked to the bar, which was three blocks away. The five inch heels gave me no problems and I was still about an inch shorter than Chris. We didn’t even get carded, when Chris ordered our drinks, a Jack and Coke for himself and a Long Island Iced Tea for me. He wanted to make sure that I would be uninhibited enough for what he had planned later. We spent a couple of hours at the bar, and there were a lot of guys in there. I felt quite a few eyes on me, and it made me feel very uncomfortable yet it was a real ego boost to know that they wanted me.
What I hadn’t realized was that Chris had taken me to a gay bar, and when he went to the bar to order our drinks, he told as many people as he could that I was a sissy crossdresser. He told me that tidbit much later, and it became our regular spot, when we spent the weekend in town. I was on my second Long Island Iced Tea and really beginning to feel it, when a handsome Black man as big as Chris came to our table and started chatting with us. The more I sipped my *******, the more my head began to swim, and the more it seemed that this man, David, was flirting with me. I looked over at Chris, who was smiling. I smiled back, truly oblivious to what was going on.
When I finished my *******, Chris suggested we leave. I didn’t realize that “we” meant David was coming with us. I got up and couldn’t balance on my heels, so I took them off and walked barefoot. I was maybe 20 feet out of the bar, when I saw that David was walking with us. Like a bimbo, I asked him if he lived near where we were staying. He laughed and told me he was staying with us tonight. I was so tipsy that I just smiled and told Chris that it was nice of him to let him stay with us. They both laughed at the same time.
When we walked into our room, Chris told me to get on the bed and dance for them. I got up but the alcohol was preventing me from keeping my balance and I fell, but thankfully I didn’t fall off the bed. I was laying on my back, with my head hanging slightly off the foot of the bed, and I started giggling. I said, “Oh, the room is spinning!” and Chris and David laughed. I closed my eyes to try and stop the spinning but then I got nauseous, so I opened my mouth and started breathing deeply to make it go away. It was then that Chris shoved his cock into my mouth……so I thought. I opened my eyes but a set of balls was resting on them. Chris had big balls but they didn’t hang that low. Immediately I freaked out, realizing what was going on.
Chris jumped on the bed and pinned me down so I couldn’t move. He said, “Take it easy, baby. I wanted to give you a treat, because you looked so good that first day you wore your girl clothes for me, and I knew that sharing you would boost your ego.” Being ******* makes everything sound logical and I calmed down. David resumed fucking my mouth. His cock was bigger than Chris’ too, something I didn’t know was possible. We spent the entire weekend in the room, and they fucked me mercilessly. I lost count of how many loads I had in me, but I couldn’t hold them in…cum was just oozing out.
For Christmas of 1992 Chris and I both took two weeks of leave and decided to spend it in San Fran. Chris told me that he had a special Christmas gift for me, and the anticipation was killing me as we spent the two and a half hours driving. We got to our usual hotel and I immediately changed into my girl outfit. Chris had me wear my white lace bra and string panties. I kept pestering him about my Christmas gift, but he told me I had to wait.
Once I was dressed, he told me to get on the bed, on my stomach, with my head at the foot of the bed. I did as I was told. Chris gave me a silk black sleeping mask to put on and then he tied my wrists and ankles to the bedposts. Once he was satisfied that I couldn’t move, he told me he was going out to get my gift. I told him I couldn’t wait to get it, and he laughed. It was a laugh I knew and it made me a bit nervous.
Chris came back about two hours later, and I was mildly annoyed, because I hadn’t expected him to take as long as he did, but I knew better than to say anything. Early on in our “relationship” I had talked back to Chris and he slapped me so hard I saw stars. I never talked back again. One thing I noticed was that he wasn’t alone, because I heard multiple footsteps but no one was talking, which made me even more nervous, but I was immobile and couldn’t remove my mask to see what was going on.
“Hi baby, I’m back and I brought your gift. I’m going to put this bottle under your nose and I want you to inhale, until I tell you stop. When you do, I want you to hold your breath, until I tell you exhale. Do you understand?” “Yes, Sir, I understand.”
Chris held the bottle under my nose and told me to inhale deeply. It smelled a bit fruity to me, but there was a strong pungent aspect to it too. He then told me to hold my breath for what seemed like an eternity and then he told me to exhale. Almost immediately I felt my heart pounding and I immediately got horny as hell. My cock had long stopped having erections, but my pussy was pulsing and I wanted to get fucked.
He asked me how I felt, and I told him that I really wanted to get fucked and that he should call David to come over, because I really wanted cock. Chris laughed and said, “Well I’m glad you said that, because David is here, and so are five other guys. I wasn’t even panicked at all; hearing Chris say that just made me hornier. “Well don’t just stand there, fill my holes!” My transformation into a bimbo sissy slut was complete.
Chris kept giving hits of poppers all night, and I took cock after cock after cock for days on end. Cum was flowing out of me non-stop and no Kegel exercise in the world would have kept my pussy from stretching as much as it did. I was in heaven and I didn’t want our Christmas vacation to end but it had to. I sucked Chris’ cock all the way home and swallowed four loads. It’s a miracle I didn’t get HIV during those two weeks, because it would have probably killed me, considering Freddy Mercury had died of AIDS the year before, and meds to treat the disease weren’t what they are today, AND we were in the gay Mecca of the United States.
Chris graduated three months before I did. I was hoping that we would be stationed together, but I was going on to Arizona and then home; he went to Germany. He was gone before I got home from school. His stuff was gone and there was no goodbye note. I fell to the floor and started crying uncontrollably. I was mad and I couldn’t understand why he would just leave without saying a thing, after I had completely given myself to him. My girl-friend came into the room and sat down next to me, putting her arms around me.
She told me that Chris had knocked on her door and asked her to give me the keys to my chastity cage and that he wasn’t good with goodbyes, so he asked her to say goodbye to me for him. I couldn’t stop crying. She just kept hugging me and telling me to let it all out. After a half hour, I composed myself and felt stupid for crying so much. I asked Heather to give me the keys to my cage, so I could take the damn thing off and to my surprise she said, “Let’s keep it on a bit longer”. The submissive in me kicked in and instinctively said, “Yes, Mistress”. Heather laughed at my reply and said, “I love the sound of that! You just opened Pandora’s Box, Jenny!”….no one close to me called me by my boy name anymore. Heather told me to put a cold, damp cloth on my face, to reduce the puffiness in my eyes, and she was going to take me to dinner.
Once my eyes went back to normal, I got undressed. Heather had seen me naked a thousand times, so it didn’t bother either one of us in the slightest to see the other one without clothes. I went to my drawer to get my boy underwear out, and there wasn’t any. Chris had taken them all. I cussed. Heather laughed and explained that it was actually her idea for him to take them, because she wanted to keep me in the life to which I had become accustomed. She told me that she had decided that she was going to take over as my domme but that there would be zero traditional sex involved between us.
Instead, she was going fuck guys in front of me, and my job would be to clean them up, when they were done. I wasn’t sure about her idea and told her that I thought of her as a sister. She told me that she thought of me as a sister too, but this was non-negotiable and I would do as I was told or she would throw my chastity cage keys into Monterey Bay. I was incredibly turned on, but my clit had no response, so I reluctantly agreed. She finished by saying, “Besides, I hear you’re a great cocksucker, and I want to see if you’re better than me.” I smiled.
That part of our relationship was, I’ll admit weird for me. In fact, to this day we don’t speak of it, but she did give me back the keys to my cage, and I still have it.
As I got older, I married a woman, because I wanted to fit into society’s idea of “normal”. I tried to discretely share my proclivities with her, but she had no interest in it. She did use the black 8” dildo that I bought her, but then again, so did I. Several times during our marriage I got the urge to get fucked, so I created a profile on a gay hookup site to satisfy my cravings. We realized after 10 years that we had nothing in common, so we went our separate ways. I finished my career in the military and got fucked a few more times but continued to try to conform to society’s definition of “normal”.
I’m now 45 years old and realize that there is no such thing as normal. In fact, the last time I felt “normal” was when Chris and I were together and I was living as a girl full time. I felt normal with that chastity cage on my clit, and I felt normal when I had a Big Black Cock inside of me and being bred.
So, to end this diatribic monologue, I’ve decided that I’m going to transition into Jennifer full time and say goodbye to society’s version of “normal” me. My goal is to do this in stages, starting with hormones to get rid of the testosterone in my body and replacing it with estrogen. I want to do everything I can to grow natural breasts, so that I can get big silicone implants. I want to be castrated, because I never liked that annoying sack between my legs. I may or may not have my clit removed and turned into a man-made pussy.
I DO know for sure that I want someone to take control of me again and give me that secure, “normal” feeling again. I am not opposed at all to being a cuckold again. As weird as it was with Heather, I did enjoy the humiliation of being told I didn’t measure up to her bull and then being told to clean the cum out her and clean the bull’s cock. What I would really love, though, is to become a Black man’s property again and be his bimbo fuck slut forever.
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