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How i became a sissy cuckhold slut pt 1
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How i became a sissy cuckhold slut pt 1 Just a little blog or story or whatever you want to call it about how I started crossdressing and came to really enjoy cuckhold and “forced bi” play. I first started dressing and acting like a girl when I dressed in my tween years. I had a male friend who one day we just started fooling around by kissing and started a game we called “husband and wife” and where I always seemed to be the “wife.” After weeks of this game that turned me on and I enjoyed a great deal I decided to take it a step further and dress up in some of my older sister’s underwear and clothes. I figured if I was going to play the female role I might as well dress the part. I named my female persona Danielle. My friend loved it as I did and soon I started using makeup and purchased some cheap wigs from a local party and costume store and began practicing being more feminine. After a while our kissing turned into mutual masturbation, then oral sex (me giving and him receiving) and then later he took my anal virginity. While I loved it and loved being his “wife” we both knew we were not gay but bi-sexual and out game lasted close to a year. Soon he started dating a girl and our game ended for the most part, on occasion he would ask me to dress up for him and fuck me but that became rarer and rarer and I also started dating a girl and got out of crossdressing. At college I dated girls and secretly had a few guys I enjoyed giving oral to but never got back into crossdressing even though I missed it. I was not feminine acting in public but just an average masculine male. It was not until I met my wife (now ex-wife) that I became Danielle again. I started dating Jenifer when we were seniors in college. We both had the same major and were in several study groups together and I was immediately attracted to her but she did not feel the same way. Jenifer was a very pretty girl who I considered very beautiful. She stood about 5’ 6”, had short blonde hair cut into a pixie cut, alabaster skin, and a lovely heart shaped face. Her body was perfect. Nice C cup breasts and a perfect ass. She was one of those girls that had a naturally firm body and could eat anything without gaining weight. Like me she was from the South and was a perfect southern lady with impeccable manners and such a sweet Southern accent that was not redneck or harsh but subtle and sweet to listen to. One problem I saw was she had a boyfriend of 2 years. Her boyfriend was the jock type, muscular and extremely handsome. In my younger and college years I was cute, had a thinner body but not muscular. I enjoyed exercising a lot but my work outs did not consist of weight lifting but more cardio such as running so I had a nice body without all the muscles as her boyfriend had. I asked her out several times and she politely declined but we became friend’s, good friends. Through our friendship I found out she was from a well off family, went to private school, and a very “good girl” who blushed ever so sweet when the topic of our conversations turned to anything sexual. I dated various girls off and on throughout college and Jennifer would often tease me about the type of girl I normally dated. For some reason I always seemed to date the trashier type girls and Jennifer found that amusing and would always tell me I needed to date a nice girl. I of course kept my secret from her, how I used to and enjoy dressing as a girl and my bi sexuality. One night we were in her off campus apartment alone and we were drinking and spontaneously started making out. Our make out sessions lasted for a long time but never got passed the stage of me fondling her breasts and her rubbing my hard cock through my jeans. After a while she seemed to sober up and said she could not go any further and started to feel guilty about her boyfriend and so sweetly and politely asked me to leave. We did not talk for about two weeks as she seemed to do her best to avoid me and one day after one of our study groups she said we needed to talk. Dreading the end of my friendship with a girl I was now in love with I just nodded my head and followed her outside the room. It was then that she shocked me for the first but not the last time. Jennifer said she broke up with her boyfriend because she wanted to date me and if I was serious and interested I was all hers. She told me it was just wrong of her morally to date two boys and that was why she did not talk to me for a couple of weeks why she sorted out her feelings but she said she came to really like me over the past months of our friendship and lost interest in her boyfriend because of me. I was elated and naturally agreed. We dated for about a month and a half before we had sex for the first time. I knew she was a good girl who did not just go around fucking people, she even told me she had only been with two other boys sexually and insisted I go to the college health clinic to get tested for STD’s since she knew the type of girls I was used to dating. My second shock she gave me was her sexual desires and drive. I expected our sex to be just “normal”. But she surprised me when she gave me a blow job and allowed me to cum in her mouth, she surprised me by asking me to go down on her until she came, she surprised me by the amount of sex she wanted that first night, she surprised me by her dirty talk (during our first time she used the word “fuck” several times, something I never heard her say before along with other “dirty” words I never heard her utter), and she surprised me in the amount of times she orgasmed. She would orgasm often and hard. I liked to think it was me but I knew it was just the way she was but it did make my ego inflate a great deal. After hours of sex we lay in bed between fucking and I teased her about her very loud almost whimpering moans, how she screamed out in pleasure, and her dirty talk. Jennifer blushed as she snuggled next to me and told me I surprised her also. I asked her what she meant and she blushed again and did not answer until I pried more. I discovered Jennifer was very sexual and enjoyed a great number of things done to her and enjoyed doing a number of things but would get embarrassed talking about it unless we were having sex. “Well…ummm…ok it is that you like to have sex a lot for starters.” She commented. I laughed, “Yeah doesn’t everyone.” Jennifer laughed, “No I mean that well…ok my ex for as how he looks and his body is so toned and built well…ummm…he is well…he is a one timer. I mean we had sex and he would then roll over and go to sleep. He would make me orgasm but then that was it.” “Awww poor girl.” I teased. She playfully slapped my chest, “Hush...and well he hated doing stuff to me with his mouth. Hated going down on me and you seemed to love it and well…I loved how you would use your tongue on and in my butt…it felt so good. And…and I like how you are not well…how you don’t shy away from kissing me after I put you in my mouth or after you did it in my mouth. My ex would not even kiss me until I brushed my teeth after we did that.” That was true, I did love giving a girl and even a guy oral a great deal and loved rimming and enjoyed the taste of my cum on my partners lips. I did not tell her, but I enjoyed the taste of a guy’s cum a great deal, even ate my own often after I masturbated. “Well I like to enjoy and explore things, Jennifer. I am not ashamed or embarrassed to explore things sexually and I always believed that the couple should talk about what they like or dislike without any judgment no matter how kinky or embarrassing it may be. Don’t be ashamed of asking me anything or to try anything. If I am not into it I will tell you and I hope you would feel the same way. I think honesty like that is very important.” Jennifer smiled and kissed me and then moved her head down to my now semi erect cock and started sucking it once more. It was about two months before Jennifer opened up more about some of her sexual desires and things she wanted to try. Our sex life was great and so fulfilling as well as the other parts of our relationship. I could not believe this beautiful girl who was out of my league told me just a week before she loved me. It was one night after some heavy and even kinky sex, she wanted me to tie her up which I did, and she was lying in my arms and shyly asked me a question. “So ummm…do you ever watch porn?” I laughed, “Yes what guys does not. You?” She blushed, “I have some but not really into it. You know when I am with my girlfriends and we watch it just for kicks…but it’s not really for me. But there was one we watched one time I well...i kind of wanted to well…I wanted to try it.” My curiosity was aroused as well as my penis, “Oh what?” My mind was filled with thoughts of threesomes, with her and another girl but her answer shocked me. It took quite a bit of prying but I finally got it out of her. “Well…there was this girl and she ummm…she did a guy…she used a strap on and fucked him in his butt. I thought it was very hot and erotic.” I was shocked, I had anal sex done to me when I was younger and used to dress as Danielle and enjoyed it a great deal but never had one of my girlfriends do that or even desire to do that to me. I told Jennifer we should be honest with out sexual desires so I thought it time to tell her the truth…or at least part of it; plus the thought of her fucking me turned me on a lot. I told her about my childhood tween friend and how we explored or sexuality and how I gave him blow jobs and allowed him to fuck my ass but left out the dressing up as a girl. I was afraid of her reaction but once again she surprised me. “Wow…I never explored anything like that with my girlfriends. I kissed one of my best friends once when we were fifteen…we made out…but that was it. I think that is kind of hot what you did.” I sighed in relief, “Well I did not have rich prudish friends growing up like you did.” I told her and she laughed. She asked some questions about if I enjoyed it, when was the last time, etc. and I told her that I had not done it since I was my friend but had given a few guys oral sex since starting college. She was not disgusted nor did she get mad but it seemed to arouse her more and she begged me to fuck her again. It was a week later when we went to the local adult sex shop store and bought her a strap on. I found it very amusing how embarrassed she was and how it took about 15 minutes before she even got out of the car. I found her shyness and embarrassment about sexual things when not in the bedroom adorable. We picked out a nice strap on dildo of average size, she choose a pink one, and a few other toys like a vibrator for her (she confessed she never used one when she masturbated and thrilled to have one) and a male masturbation toy that looked like a girls pussy, and of course some lubricant. That night we used the toys often and she fucked me in my ass two times. The first she lay on top of me and spread my legs and fucked me as I jerked my hard cock until I came and the second time she took me from behind and she jerked my cock until I came again. It took her a while to get used to doing it and I admit the first time hurt at first because it had been so long since I had been fucked anally and she initially penetrated me hard and fast, but she got the hang of it. Again she shocked me when she fucked me, as she fucked my ass she would yell out that I was her bitch and ask me if “her” slut liked getting his ass fucked. I loved it! It was a huge turn on to hear this prim and proper girl use such language. Later that night she told me it was only fair that since she fucked my ass I should fuck hers and I took her anal virginity and after she said she loved it; she did not have to tell me because she came very hard when I was fucking her ass without me even touching her pussy. So our sex life was awesome. We could not keep out hands off one another and once even had a quickie in the college<b> library </font></b>in a secluded area. Jennifer had to cover her mouth with her hands to prevent from being heard. She would use the strap on to fuck my ass about 3 or 4 times a month and really enjoyed when I fucked her ass much often. We were so in love with each other and even our non sex life was great, we spent every moment we could together and she took up running to be with me. When we jogged I always let her slip a little ahead of me because I loved seeing her great ass in the short, tight jogging shorts she wore and by the looks of the other guys and even a few girls on campus as we jogged by I was not the only one. After we graduated we got married much to her parent’s disapproval. They never approved of me and thought I was to low class to marry their only . They hated everything about me, me coming from a broken home (my mother and father were divorced since I was four and I had not seen my father since I was six, he never wanted anything to do with my sister and me), they hated I was catholic even if I did not practice it since they were Southern Baptist, and so many more things. I tried my best to get them to approval of me for Jennifer’s sake. I was charming to her mother, went fishing with her father, but nothing works and Jennifer told me to just give it up. She told me she did not care what they thought of me, she loved me and that was what mattered. On the contrary my mother adored Jennifer and my sister became one of her very good friends. We had a nice small wedding paid by her parents for appearances sake and honeymooned in Aruba, a wedding gift from her father to her. Jennifer brought along her strap on with her on our honeymoon and besides the awesome sex we had a wonderful time. On the fourth night of our honeymoon after she fucked my ass we lay in bed cuddling and waiting for our next go around when I confessed how I used to dress as a girl for my childhood friend. Jennifer just smiled and commented how sexy that was and teased me a little saying she bet I made such a cute girl. It seemed to be forgotten until about eight months into our marriage and our sex life took another un-expected and shocking turn. |
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