Cash Discovers His Girly Side

This is a spinoff story about a character in 'Surpassing a Cultural Setbacks'.

Cash's story

When I was younger my parents divorced, I did not really know why until I found out in highschool. A few kids were picking on me, which was pretty normal but they were now calling me gay a lot more. My parents were gay and I had always known my Dad was gay. How or why was this a big deal to other kids was a mystery. I talking to the councilor Mrs. Stevens, someone I trusted and who I talked to a few times a week. She told me that just because my dad cheated on my mom with another student's father, that did not make me gay. That actually made a few things click in my head and I finally knew the answer to the divorce, although putting two and two together might have settled it, it just was not important to me.

My mom never told me why they divorced either. I did like my step-dad, actually both step-dads. Jim was my dad's husband, I saw him a few times a month, more before my dad's accident. Since my father was no longer with us, my time with Jim was limited. Eddy was my mom's husband was pretty cool, he treated me like a son, even though he had a son a few years older. In all honesty, my short life had given me 3 of the best dad's a guy could ever ask for. Jim had moved on and was dating a black man named Shawn, even Shawn was a nice guy and I really liked him. Eddy's son was Brice, Brice and I butted heads often, even some physical altercations which I lost. that was because he was in college and built more like a man than my twig body.

My senior year I did get a lucky break when a girl I asked to the movies agreed to go. She had graduated the year prior. Jane was not going to college and was just hanging around living with her mom and wasting her potential. Eventually, I asked her to be my actual girlfriend and she agreed, after a few months of dating we talked and we agreed to wait on sex for marriage. We were both 18 and I wanted it, I think she did too, but we thought we were doing the smart thing.

In school I was having trouble with some a classes and whenever I had a big test coming up, Mrs. Stevens like always helped me prepare, I thought she was the best part of my highschool experience. One time I missed a test time because Mrs. Stevens messed it up the schedule. The next time I thought I did well, but turns out some of the material we studied for what all wrong. I could not understand how Mrs. Steven's had so many successful students, but with me she seemed to drop the ball every time. I even studied for an additional test as a make up exam. I went to the exam, turned my test into Mrs. Stevens but the exam never showed in the system. This was my last chance to place for the college I had been trying to get into and now I was not going to be able to go anywhere or do anything. Since I was now 18 I needed to find some way of making cash.

When the summer after my senior year started I spent a lot of time with Jane, she had a pool and now she had part time job. Sometimes she would invite me over to hang out while she was still driving home from work. I sometimes changed into my swim shorts in her room and waited. Usually she was only a few minutes behind me, a few times she walked in on me when I was almost naked.

One day she invited me over as she had done so many times before. I had already changed, when I heard her coming down the hall loudly, this time she sounded like she had someone with her. I peaked out and she was being pushed against the wall by a man that was kissing her. This was not a guy around our age, this man was 30 or maybe even 35. He was muscular and his shirt was off as he was groping my girlfriend's large breasts with his veiny muscular hands. He had his tongue in her throat and she was returning the affection. I was upset and confused, angry even. I did not know what to do. She had invited me here, even if she was the cheating type, which I believed she was not, why was she allowing this man to manhandle her like this. Maybe she was being blackmailed, that was the only thing that made sense in my mind at the time. I thought about confronting him, but this man would have beat the lever living shit out of me. What good would I be if I was lying on the floor with a broken nose, crying, or worse. I was scared and needed to find an action plan.

Thinking quickly I went to her walk in closet and closed the door. It made sure it never clicked, I did not want to make a sound. I also silenced my phone, fearing a unwanted discovery by this man. Jane entered with this man pretty quickly after I was in the closet and it her actions made it seem like she was not being forced to do any of this. I listened and after a while got interested and decided to peak. I watched as my girlfriend sucked this man's cock, it was 7 or 8 inches. She seemed to really love sucking it. What shocked me was their conversation through out the 45 minute fuck session. I did not know the girl I was dating at all.

She said, "Danny baby, you always have the hardest cock for my pretty little mouth."

Danny said to her, "Jane, you suck cock better then most girls I know. My buddy Jeff tells me you are better then some of the fags he lets blow him."

She questioned him, "Jeff? Is he the one with the tattoos on his sleeve?"

He replied, "No baby. He is that guy at the bachelor party a few weeks back. Remember he and I split roasted you in the basement."

She laughed and said, "Oh, I remember. Well mostly, I was high as fuck that night."

He replied, "That was a fun night, not as fun as your eighteenth birthday party. I cannot believe you let your mom's boyfriend take your virginity in front of so many people. You are such a slut."

She laid on her back and he started fucking her missionary, she said, "You did not seem to mind. You got sloppy seconds, didn't you?"

He laughed and said, "More like sloppy fifths. There was a line and I was not second."

I was at a loss, my girlfriend had been cheating the entire time I had been dating her. There was no way she was the kind of girl I could marry and she said we could not have sex until marriage. I was never going to fuck this girl, I thought I had feelings for her. I processed my thoughts as she fucked this guy, ultimately I decided Jane and I were though. I brought myself back to reality as the pair was having their final simultaneous orgasms.

She screamed, "I love you Danny!" as she came on his cock.

I watched as this man filled my girlfriend with his cum, he did not even wear a condom, it made me sick. Not really sick because of the natural sex act or the bodily fluids being shared, but sick because Jane was a lying bitch. She had never told me she loved me and I had confessed my love to her just a month earlier.

She helped him get dressed while kissing him a few times and even zipping up his pants and buttoning them. She walked him out of the room. I stayed in the closet wondering what to do next, I did not think that part through. I did not have to think long because she came back in the room and came straight to the closet, opening the door seeing me standing right there.

She smiled at me like this was perfectly normal and said, "So, what did you think Cash?"

I looked at her nude body, something I had never seen before, "What is this Jane? You are sick! Was all of what I heard true?"

She laughed and said, "Yes, all of it. I am a slut. Now you have been lying to me too."

I wondered and asked, "How?"

She replied, "You and your small dick Cash. I saw it when you changed last week. Were you not going to tell me and have me find out on our honeymoon night? How could you?"

I was on the defensive now, "You said we should wait until marriage! How do I open the conversation that my dick is small. It should not even be an issue if you love someone."

She said, "Well, you see, it is an issue. I was actually starting to love you. I saw your dick and now I honestly can't stand to look at you. It is over, but let me give you one last bit of advice. Since you have a small dick, like a very small, you should probably just transition and be a girl. That is the honest to god truth from me, one girl to another."

I picked up my clothes and walked out of her room. She came to the hall and said, "Wait."

I turned, I did not know what for. I never said anything but she did, "One more option. You could be my cuckold. I wont ever fuck you, but it could be hot."

I turned and ignored her, I don't even know what I thought she wanted. Just to humiliate me one more time. I never talked to her again.

That night I thought about her comments. Not about the cuckold comment, but about the transitioning comment. It was true, this small 2 inch hard cock was never likely to satisfy a woman. I was not stupid and I had thought about that issue before, but my love for her blinded me. I knew if I ever had sex with a women it might be out of pity and that seemed like it would hurt my ego as weird as that sounds.

Her comment about being a girl and my thoughts about it stuck with me for a long time. I never made any move to transition with the exception of growing my hair long. I did watch porn and masturbate and I started watching gay and trans porn more and more. First it was trans porn hear and there on top of straight porn. Later it was mostly trans porn and I got interested in a certain actress that had done some bisexual and gay porn earlier in their career. I liked the actress so much that I did not mind watching two guys got at it. I did start to focus on and even begin to like the looks of some of the male performers and their cocks.

I was sitting in my room one day when Brice came to visit. My parents were out and he wanted something he could not find from them. Something his wife asked him to get. I actually tried to help him but he was being a dick and we got into an argument. He pushed me, I tried to punch him as a way to get back. I had no success in moving him or causing any pain. I punched at him again and he hit me and started pushing me to the ground. I ran at him finally knocking him off balance and we wrestled on the ground. He soon had me pinned, with his face over me. He was calling me names, telling me I fight like a girl. I finally had enough and broke. I don't know why but I leaned forward and kissed his lips.

I stopped and looked at his face. Brice was at a loss for words, this was new for his to be so quiet. When he still did not move I kissed him again. This time he responded kissing me back. The kiss soon turned into a make out session with us stripping our clothes and rolling around naked as he tried to rub his dick on me. I loved it. His dick was only about 5 inches but that was so much bigger then mine and so very hard for me. I moved position and he let me suck his dick. I was horny and I asked him to fuck me. He agreed and we made love with his dick in my virgin asshole for the next 30 minutes before he finally came in my ass.

After we were awkward about it and we agreed it was a mistake and he left. The mistake made me want more, so I searched for other men and found them a lot easier than I thought. I fucked a few guys I knew, some were married and some were neighbors. Brice and his wife came to visit for their daughter's first birthday. That night Brice came to my bedroom and we started to have sex again. He had me pinned against the wall panting like a bitch in heat when my mom and his wife came in trying to figure out what the noises were. They caught us red handed and it caused a huge family crisis. Brice and his wife went to counseling while my mom and step-dad did the only thing they could, they grounded me. Being grounded does not mean anything at 18, but I was in trouble. Brice and his wife made up and she even got pregnant again.

Eddy came to talk to me about my sexual adventures. I was becoming the talk of the neighborhood, at least in the gay community as I was known to have fucked a few married men and was not very quiet about my interactions. He told me that basically I was oversharing who was gay with other men who should not have known. I wondered how he then found out, but based on our conversation, maybe that question was better left unanswered.

I told him, "Dad, I will hold off on seeking out married me to fuck. Is that ok?"

Eddy said, "Sounds good Cash."

I asked, "Does mom know I have been with married men?"

He said, "No, and we don't need to let her know."

I was curious and had to know, "Well, how did you find out?"

He said, "Well, one of the guys at poker night suggested I bring you for entertainment. I asked why and they told me you are a better fuck than their wives or some of the other girls or guys we normally have."

I said, "You mean you cheat on mom at these poker nights? Sometime with guys?"

He confided in me, "Don't get mad cash. I love your mom, but fun is fun."

This comment pissed me off, she was my mom. She deserved better, but I was also horny and saw an opening. I never let and opening go to waste. I also knew Eddy was bigger than Brice was. I had seen my mom a few weeks before on her knees sucking his 7.5 inch cock in the backyard late at night.

I smiled and said to him, "I can be fun with just you if you want, not with your friends, but here and now."

He smiled, grabbing me and kissing me with a lot of passion. We made love that afternoon and I worked him into my routine of married men, which I never slowed down fucking and he knew that.

Sometimes I felt bad when I would realize my stomach or ass was filled with his sperm as I watched tv with or made supper with my mom. eventually my mom walked in on me riding his cock in their bed. That was the end of her marriage, she kicked him out and me too. I had no one to blame but myself and I ruined my relationship with my mom over some cock, good cock, but it did not matter.

I had no where to go so I called my step-dad Jim and told him about my error. I showed up to his house wearing boy shorts and a mesh top. After Jim let me move in with him that was a typical outfit for me. I explained everything truthfully to Jim. He accepted me and he knew I was a slut. He told me to just be safe, I did not have any control and did not know what safe was. I sure did not make my men wear condoms or screen then in any way. Jim allowed me to bring home men and sometimes I brought home 2 or 3 at a time. He was now married to Shawn and Shawn never said a negative thing about me. In fact the only time I ever got talked to was when I invited Eddy and Brice to tag team me. He let me have my fun but told me not to do it again.

I did eventually express my desire to transition. Shawn had money, he never flaunted it but he bought me some C-cup tits for my birthday. Jim supported me but he was upset about Shawn doing that without talking to him about it. After I was on all of my medication, had a few minor surgeries and voice therapy felt better. I was dressing and acting like a girl and with this nice rack, Shawn's attention towards me shifted. Before the transition, with him I was given money, attention, affection, sometimes kisses on the cheek. He was always looking at my boy body too, which I liked. Now, after the transition he wanted little to do with the girl I was. He still liked me, he was just no longer attracted to me. I was ok with that. I already lost some of my more regular partners who were only interested in boys so it was not really something I could not comprehend.

I had been debating joining the military, since my collage dreams where dashed. I told Jim and he was supportive, he had spend time in the military himself. His service was during peace time, but with the war looming he was weary, but still supportive.

I knew the military would take me away, but before I wanted to pay revenge on Mrs. Steven. She took my life off the tracks, I did not even know why, but I know knew it had to have bee on purpose. I went a bit stalker on her and followed her trying to gain insight on her life and how to pay her back properly. I figured I should use the only skill I really had. If I slept with her husband that might cause some pain. I followed her to the mall one day and by some strange turn of events I ran into Jane.

Jane did not recognized me right away but when she did she said, "Oh my god! Cash, is that you?"

I was comfortable with who I was, and did not hold resentment for her. I was actually kind of thankful for her help in pointing me in the right direction even if she was unfaithful. I replied, "Jane, wow, weird seeing you here."

She said, "You look good. I hope you are doing ok."

I replied, "I am, weirdly thanks to you. You helped me realize a few hard truths. I know it is weird, but I should thank you."

She said, "So you transitioned?"

I smiled and said, "Yes, I am so much happier now."

She asked, "What are you doing around here? I never see you around and I am here all the time."

I told her my mission, or at least part of it, "I was actually following Mrs. Stevens. She screwed me over in highschool and I don't know why."

She laughed and said, "Cash, You don't know, do you?"

I apparently was in the dark and I asked, "What?"

She is a total homophobe, her and her husband. They knew your dads were gay and she sabotaged you. You and every other gay kid or kid with a gay family."

I wondered, "Was I blind to it?"

She said, "No hard feelings Cash, but you were blind to a lot. I hated what she did too you, but honestly I did worse. Sorry for that, I like to think I have grown, but it was terrible."

I finished my conversation with her and soon a 'date' came to take her away.

For Mr. Steven's I now knew I needed to pretend to be a girl, and not outwardly fruity sissy or tranny to fuck her husband. I needed film it and release it to her and that would destroy her homophobic ass.

This is how my plan played out. The Steven's lived out of town on a dirt road. I drove out there and faked car trouble near their house when Mrs. Stevens was out of the house. I convinced him to let me inside and while he was in the kitchen getting a drink for my parched lips, I set up two hidden cameras in the living room pointed to the couch. Seducing him was almost too easy. I made out with him and then I sucked his cock, making sure he did not cum. I told him I was saving myself for marriage, but if he wanted her could fuck me in the ass. Men are too easy, most 'straight' guys always give in to trans sex when I mention anal. I told him to fuck me reverse cowgirl, I kept my panties on and my small bulge out of site while we positioned. Once I could I pulled out my little dick and played with it while he fucked me. He focused on my back and ass for his visual pleasure luckily. I was afraid he would find out before he got off, but I already had what I needed. I even told him I was playing with my clit.

Once he filled me up, I stood and allowed him to see my penis. He freaked out and ran out of the room. I collected my cameras and split. I edited the video to include both shots and left out the part of him freaking out. It was almost too good. I then drafted a email to her, all the teachers I knew were her friends at school, him and his employer. I included her wrong doings. I hit send and the fallout and repercussions were fast. They got divorced, she was put on leave and he was not fired for some reason.

There were positive side effects from this for me. I had 3 male faculty members reach out to me, none were in the email. They wanted dates with me. I fucked them all before leaving for basic training.

A few days before I left for boot camp my mom called me, we had not spoken in almost a year. I told her over the phone I was transitioned and she wanted to see me. I met her at her house alone. She showed me some changes she made to the house. She was happy for me and finding a new path in life. We talked about how I messed up her marriage, I apologized a few times, in the end she did say that she knew he had been fucking around on her and it was a matter of time. I told her about how Jane cheated and how my penis was too small for any woman, transition made sense. She agreed that if I was gay, transitioning was probably a good idea.

I had a good night with her, we bonded better as mother and daughter then we ever did as mom and son. We even talked about our sex life. Nothing was taboo anymore. I told her about how I invited Eddy and Brice to double team me, she agreed it was a bad idea, but pretty wild on my part. She even told me that she had let her guard down a few times and let Eddy fuck her again. She said it was kind of cool knowing we fucked the same man. She asked me about Mrs. Stevens and I told her the whole story. She told me how when she heard about her husband and did not know it was me, but she called the district and pushed to get her fired because it reminded her of some of the issues I had because of her.

After that she had a glass of wine for each of us and we drank. She admitted that she was envious of how free I was with sex at my age. She wished she could have had more sex before finding my father.

I said, "Mom, if you could be my age, what would you try? You know, if you were as free as I am?"

She replied truthfully, "Cash, I would probably look to get fucked doggy style and suck a big cock at the same time. That sounds so dirty and hot. I can't believe I told you that."

I said, "If I can get two guys I know would you be willing to make that dream come true? Would you let me call them?"

She replied, "That is so wrong, having my son, oops, I mean my daughter, set me up on a group sex date."

I grabbed her hand and said, "Mom, yes or no."

She answered, "I can't believe I would do this. Yes, please don't think bad of me."

I eased her mind, "Being horny is natural, I take advantage of being horny and horny men all the time. I helps two people, sometimes more, like tonight get what they need. You go get ready for your men. I will get them and let them in."

I called two guys I graduated with and who I had fucked a few times when I lived at home. They were both bisexual and I knew they would love my mom. The first one agreed readily saying he always thought my mom was super hot. The other guy only agreed if he got to fuck me after. I told him if he still had any juice in him after he was done with my mom he could come to my room. I told my mom about the second guys plans and she seemed to be ok with that.

After I let them in I went to my room. I sat in my bed and listened to my mom having the time of her life with two young men. About 2 am I heard the first man leave, and about 20 minutes later my door opening and the second guy came in. Mom had made him shower with her and then sent him to my room. We fucked for a good hour before I was able to finally get his sperm load. He wanted to spend the night but I sent him home.

In the morning my mom thanked me for setting up the date and we talked about how much fun she had being treated like a slut. She wished me the best and I told her I would write, or call if I could.

The night before I left for boot camp I asked Jim and Shawn if we could have sex. Shawn allowed Jim to fuck me but there was no threesome. I still think he had issues with females and transsexuals. I loved sex with Jim more then I should have, he got off on me calling him Daddy and I did too. We promised to do it again, but never behind Shawn's back.

Boot camp was dry, I was only able to suck off a few guys and a few instructors, but it was tough. At boot camp graduation I learned I was going to school with Cody, Kate and a handsome hunk named Isiah, he was a muscular black guy. I was friendly with Kate through boot camp as we were the only transsexuals in that class. Cody seemed to hate me and Kate for being 'gay'. He did not seem to like Isiah either, which was weird, every one loved Isiah.

After graduation, the night before we shipped out for training I spent the night with 2 guys whose girlfriends could not make it to visit them. It was their loss and my gain. Both men loved my asshole, they had never fucked a ass before, so they spend a lot of time back there. On the bus trip I made friends with Isiah, even sucked and fucked him a few times on the trip to our training station. Kate and I were already almost friends, although she too did not fully like Isiah. We sucked each other off on the trip and she seemed to be making friends with Cody which seemed like a huge accomplishment.

While at training I was able to break away with some civilian friends for a day trip and meet my step-dad. We were supposed to just have lunch. Jim told me him and Shawn split up. I took that as a sign to come onto him and we spent a few hours in his hotel fucking like rabbits. We did more then fuck, we talked too. He told me he talks to my mom more now that Shawn has been gone. Apparently my mom has become a proud slut in a short time I have been gone. He told her that he fucked me before I left and even told her he was going to see me and likely fuck me again. I went home that evening with a load of my step-dad's cum in my belly.