I became a cock sucking fag Pt 10
After my initial night with Claire, I was somewhat uneasy about anything further with her, not because of the sex, but because of her relation to me. I had enjoyed being with her, and our conversations and admittance of our bi-sexual pasts had opened the door for a lot of trust and camaraderie with one another. Truthfully, it was amazing being with a woman again and I was very comfortable doing it because we had developed that belief and interest beforehand. As uneasy as I was knowing that night was coming, once it hit, and we were in the process of making love, all those fears and apprehensions eased.
We continued talking by text and phone calls for the next few weeks. I was enjoying our conversations and the depth to which we would discuss personal wants and needs and I knew as much as I still was leaning towards trans women, or a man, she was leaning towards women. Sounds strange right? That two people who had just had sex some weeks back and were "into each other" still wanted someone of the opposite sex. But I think that's what made our dynamic unique. We both knew we could love being together and experiencing things physically, but in our hearts, we knew the opposite sex was what we wanted. After some time, Claire finally admitted to me outright that she wanted a girlfriend. She wanted to be in a lesbian relationship and wanted pussy. And I openly acknowledged, and truthfully knew and accepted, I wanted dick.
I think as our conversations, understanding, and acceptance of each other's different lifestyles flourished, it truly gave us both the opportunity to have deep thoughts, resolve our deep internal conflicts, and gave us the chance for both of us to accept who we truly wanted to be. Coupled with that was the fact that if either one of us were to change sides, we knew it was because of our conversations, communications, and support that any transition would be smooth and accepted. Without fear or apprehension. Surely without judgment against each other and the ability to communicate even after any new same-sex relationship would develop.
I couldn't tell you how many nights I had my hard dick in one hand and my phone in the other as I read her comments about wanting pussy. How some brief experiences and our conversations made her realize she wanted a woman again. It was such a turn-on to read a message from a woman, I knew as straight, had known for 30 years, who I had already fucked tell me in essence, she wanted pussy. How she had wished for years that she had a girlfriend. To scream to the world, that she was in a lesbian relationship. But for whatever reasons, her inability to meet someone, her fears, and overall acceptance kept her from doing it. How erotic it was to know that somewhere in her future, in the privacy of her house, late evening, she would have her face between another woman's legs, eating pussy, as she has wanted to do for years. Our conversations finally made her realize it, and I was proud she shared them with me.
Yet, just as exciting as it was to read that and know where she was at in life, it was terrifying, life-altering, nerve-wracking, and stomach-twirling for me to admit to her, writing out, that I wanted a boyfriend and needed dick. But it was something I had to admit, had to say, and had to accept. It was in essence the first time I admitted to anyone, besides myself, that I wanted a boyfriend, and that I'd rather have dick. And I got just as hard, just as excited, and just as enlightened writing it out. Countless nights after our conversations, I would masturbate thinking of having a boyfriend. Cumming hard moaning out, I want dick!
As Claire and I progressed, we slept together when either of us had the chance to get together. We kept that bond and that physical interest going. We kept things quiet from our family members and kept our passions, conversations, and desires between us. Yet, we basically agreed to have sex when we could, but further our acceptance of both of our developing "gay" lifestyles. We in essence were building up, what I would call, our last straight sexual encounters, before we both changed sides. Our last hurrah, if you will. I have no doubt we both knew it was coming. She was undoubtedly now looking for a woman, and I was undoubtedly looking for a man.
One evening through texts she bluntly asked me if any woman had ever fucked me with a strap-on? I advised her I had not but might entertain the idea with the right person. Claire wrote, "Well, maybe the next time you are here, we can go to the porn store and see if there's one you like. Maybe, we could try."
I had no issue with it, outside of it being somewhat odd, that she would want to fuck me that way, and that it was going to be rather emasculating to be fucked by a fake dick. But I was willing to try. She knew, as much as I did, that even though I had enjoyed our private time alone, I wanted cock. So, I think in her mind, this was an opportunity for us to explore and give me what I needed because she was all woman and had no dick to offer. And the suggestion was made to see if could find some body-form fake pussy for her to play with.
A few weeks later when I headed up to her for an overnight, we went to dinner and then right over to the porn store afterward. We walked around the store looking at toys, little vibrators, and dildos, coming down the aisle of strap-ons. We found this smaller pink 6" harder rubber strap-on, that had the fake dick sticking out straight, but one that was insertable for her pleasure as well. It wasn't too big, about the same size as my dick, and since it wasn't girthy and looked to be normal and average in size we decided it was worth the purchase. We paid for the strap-on, got a bottle of lube, and made our way out of the store.
I don't know if she was more nervous, or if I was standing at the counter watching the clerk wring us up, knowing he was surely thinking, this woman is gonna fuck this man with this tonight. It was very unnerving, to say the least.
When we got back to her place, we sat on the couch sipping wine and just enjoying each other's company. We kissed and cuddled, as lovers do, but when we both had a bit of a buzz and our hormones were amplified, Claire spoke out, "Why don't you go make yourself comfortable in bed and I'll get into something more comfortable."
I entered her room took off my socks, pants, and dress shirt, and crawled into her bed wearing just my T-shirt and underwear. I heard her fumbling around in the kitchen area, then head into the bathroom. I could hear her opening the package and seemingly getting herself situated. I can tell you my stomach was doing flip-flops and if it wasn't for the buzz I was having, I would have been a nervous wreck. I knew what was coming, she was going to be wearing a strap-on, and I was going to be getting that strap-on. As different or unique as it was, the time for bold talk, being "manly" through texts, and believing I could handle it, was all about to come to fruition right before my eyes.
Just as I was getting more nervous and more uneasy about the situation, I heard the bathroom door open. Within a second Claire stopped at the frame of her bedroom door, her head the only thing sticking through. "Hi," She spoke. "Are you ready for me?" She asked.
"Yes," I replied, with a dry throat.
Claire proceeded to enter through the doorway. She was wearing a light pink, open-chested, waist-length negligee. Her tits hanging low, her brown nipples showing through the material, and her "new" pink dick sticking out from between her legs. The black plastic strap holding it around her waist, her legs closed, but slightly shifted, because the other half of the strap-on piece was already inside of her.
"Do you like?" She asked.
"I nodded my head yes, and fearfully mumbled out, "It looks good on you."
As Claire came closer to the bed, she leaned down and kissed me deeply. Her hand gently caressed my face, her tits hanging low, almost popping out of the belt tied open negligee. "Do you want to suck it first, or should we just cuddle in and see how this goes?" She asked me.
"Kiss and cuddle first," was my answer.
Claire slid into bed next to me, pushing her body up against mine. We both lay on our sides as we kissed, rubbed a touched one another. My hands were all over her tits, under the negligee, while her hands were rubbing up and down over my chest under my T-shirt.
When she was ready, Claire slid her hand down my body and into my underwear grabbed a hold of my hard dick, lightly stroked me, as our kiss deepened. Her free hand guided my hand down onto her pink new dick and I started holding, caressing, and stroking her dick. (For the remainder of the story, I will refer to the strap-on as "her dick" so there's no confusion).
Claire slid down, breaking from our kiss, lightly kissing her way down my chest, past my stomach, sliding my underwear off, and putting my hard dick in her mouth. She sucked me for a while, and as much as I was turned on because we were about to make love, I wasn't fully erect and was very nervous because of that toy. I wasn't quite sure why. I had been with Trans women before, had sucked real dick, and even had been fucked, but something about her wearing a strap-on made me very uneasy.
When Claire made her way back up my torso and her face met mine, she spoke, "Do you want to suck my dick?"
I nodded yes and as she rolled onto her back, I kissed her lips one last time, made my way to her tits, sucked on both nipples and then proceeded to slowly and seductively kiss my way down her stomach to her hips. I could see her dick sticking upwards, pink, new, erect, and ready. I edged my body down further and got deeper under the covers. I grabbed her dick in my hand and just held it, staring at it. I could tell when I grabbed it, that the pull of my thrust, shifted the little insert inside of her and she moaned out a bit because it had moved inside of her.
I leaned my head down and slid her dick into my mouth. It was surely different from a real dick and it reminded me a lot of the dildos I had experimented with for years now. It was hard, yet rubbery, was long, but not to the point of gagging me, and as much as I was sucking on it like I was blowing Jillian or Geenah, I felt it awkward because I knew my mouth wasn't pleasing Claire as if it was real.
I did my best and just tried to stay focused on sucking it, moving it how or when I could, so the little insert could give her pleasure too because I knew she wasn't feeling anything tantalizing even though I was sucking that dick. I could hear her moan and groan on occasion and whimper out words, like, "Yah suck my dick baby." And, "You like that cock, don't you?"
I knew she was excited and enthralled by wearing it, almost being the aggressor or man of our situation. I think it was a very kinky and powerful feeling for her knowing I was sucking her dick, while she was getting ready to fuck me with it. Just like any man would be with his woman.
As I sucked it, I slid my finger in between her ass cheeks and I was rubbing, and teasing her asshole because I wanted her to feel pleasure, just as I was feeling pleasure in trying something new. At first, I was very nervous about all of this, but as the minutes went on and I kept sucking her dick, playing with her asshole, listening to her whimper and moan, I got more into it. On occasion I would grab a hold of her dick, shaking it, pulling it, and moving it around, letting the little insert pleasure her. I was rock hard and I was ready for her to be sucking my dick again.
I flipped the covers off of me, got up, shifted my whole body around, and laid my face between her legs, while I put my cock right at her face. She dove in just as I did and we both started sucking each other's dicks in a side-to-side 69, becoming more orientated and familiar with them. I was sliding my finger in and out of her ass, listening to her moan, as her fingers, which had reached around me, were now playing with my asshole.
