The Making of Monica Ch. 08

Losing my anal virginity!

About a week and a half after Jessica and I had our first sexual experience. I wanted to spend the night with her. Even though we had just had an oral experience, I knew in my heart that I wanted more. I wanted more of her. I wanted more dick and I wanted her to be part of my life. I texted Jessica and asked her if she would like to spend the night. I told her maybe we could go out for dinner, then a movie perhaps, then home for desert and to spend all night together.

She seemed pretty excited about it, but she just wanted to be sure that I was comfortable (at this point of our dating) for an overnight guest. I told her I was and she agreed.

Late Saturday afternoon Jessica arrived at my place. She had a small overnight bag, which contained some clothes, toiletries and other personal items she needed. We hung around my place for a bit until we got hungry.

Jessica was wearing a tight pair of blue jeans, a lose fitting white shirt and brown ankle boots. I wanted to match her outfit, so I put on a nice pair of jeans, a lose fitting pull over shirt and my cowgirl boots. We headed down to a Chinese restaurant, in the same area we had our first real date some weeks ago. As we sat and dined the waitress kept calling me Ma'am. I think she knew I was a boy dressed in women's clothing. But I didn't care. As I said before Jessica is completely passable, with her sweat high tone voice, her sexy skinny body, her developing breast, while me -- on the other hand - still needed some work. Either way, I was out being all the woman I could be, with a trans woman and someone I cared a lot for.

After dinner we went to a sappy romantic comedy and sat in the theater arm in arm. We held close leaning into each other throughout the whole move. I was absolutely smitten with her. I wanted every bit of her. I could smell her hair shampoo; I could almost taste her light perfume. I wanted to kiss her in the darkness of this place. I wanted to undress her. I wanted her dick out. I wanted to suck it. I wanted her to suck mine and most importantly and without reservation I wanted her to fuck me in the ass.

After the movie we went back to my place. We sat around on the couch, not drinking but the mood and atmosphere was intoxicating. I wanted us to move forward. I wanted us to be wrapped in each other's arms, naked, sexual, erotic. And even though I was nervous she was gong to be there overnight, I was just as excited. I think sometimes -- at least at first -- its hard to "plan" that first overnight. Sometimes I just has to happen during the natural course of dating, and I knew what she meant when she questioned me about being comfortable. But I was happy she was there and I was hoping my nervousness would ease.

Jessica and I cuddled on the couch watching TV. Neither of us making any real sudden or fast moves to get the other into the bedroom. Believe me I wanted to; but I didn't want to put any undue stress or anxiety onto the situation. But in my mind, I wanted to walk her to my bedroom. I wanted to seduce her; or better yet wanted her to seduce me. As we cuddled, we softly kissed and petted, but nothing that was leading to a full make out session. But you can bet your ass, the butterflies in my stomach were going 240 miles an hour and I was on the edge of being ready to be played with.

When the moment did arise that Jessica and I engaged in a heated kiss, I felt passion inside of me that I hadn't had since out last time together. I wanted her. I needed her and tonight she was going to be all mine. Jessica pulled from our kiss, looked me in the eye and said, "Why don't we take this to your bedroom. I have something special for you."

"Okay." Was my response, as she helped me up and off of the couch.

Jessica walked me down the hallway to my bedroom, guiding me by my hand. As we got there she softly spoke, hinting for me to wait on my bed, as she grabbed her overnight bag and ducked into the bathroom.

I took her hint and wandered over to my bed. But that's when the nervousness really set in. Do I get undressed and wait for her naked? Do I put on more erotic clothing? Do I put on some music? Do I dim the lights? Have no lights on at all? Do I just stayed dressed and let her undress me?

I always envisioned my first time of full-on sex, that I would be dressed to the 9's. I would have my matching panties and bra on, my high heels, my thigh high hose, a long flowing wig. Make-up done perfectly, my nails long and painted. My perfume light and bountiful. And it would be me, walking out of the bathroom in an outfit that would make my man hard. But here I was in my room, in jeans and average looking woman's shirt trying to not panic and set the mood. I laid on my bed, and pulled my hair back up into a ponytail. By this point my hair was getting long enough that I could pull it back in a pony tail, so I usually wore my wigs, only if I wanted that long flowing hair look. But tonight, I wanted to be as natural and as free as I could be. So, I just laid there nerve racked, until I heard the bathroom door open.

Jessica walked out of my bathroom wearing a pair of see-through black panties and matching bra. She had on thigh high pantyhose and a pair of three-inch black heels. Her hair was back in a ponytail and she looked absolutely amazing. Her dick was held tight and deep in the panties and I could see it through the material. I watched her walk, slowly and sexually over to my bed.

"Do you like?" She asked.

"Oh, yes. Yes, I do." I replied.

Jessica knelt onto the bed, edging down and coming to rest next to me. We starred deeply into each other's eyes before having that first deep kiss. Her lips gloss, came into contact with mine as we made out deeply, sexually and erotically and before I could even worry about being nervous, I was hard as a rock. Her warm body pressed up against mine. Her legs intertwined with mine and we became one. We both rubbed and touched each other while I slowly rolled my hands over her sexy outfit. We dove deeper into our lust. I wanted her so bad. My cock was hard, my body tingled and my ass was begging to be fucked.

I unhooked Jessica's bra letting her little natural tits out. I softly kissed around her neck, her shoulders, along her collar bone, until I made my way down her chest to her soft smooth tits. I kissed and licked and sucked both nipples as I heard her moan out in pleasure. My hands were cupping her ass cheeks, as my face was buried deep in her breasts. Jessica lightly guided my body upwards pulling off my shirt. I had my breast forms in my bra, which she promptly removed as she pulled my bra cups down. Her mouth engaged in licking, sucking and nibbling on my nipples sending sensations through me that I couldn't even fathom.

I reached behind me and hooked my bra, pulling it off, while pushing it, along with my breast forms onto the floor. As we laid back down onto the mattress, with her body partially on top of mine, she had no idea how hot and erotic this was for me. I knew where I wanted this to go, and I hoped she would indulge in every pleasure and fantasy I was concocting in my head.

Jessica kissed deeply, softly and lovingly for a while until I felt her hand running up and down my outer thigh. Her soft touch was highlighted by her deep kiss and the fact that I wanted my dick out. More importantly I wanted her dick in my hand, in my mouth and up my ass. Jessica fumbled with my jeans button for a second until I felt it pop open. Her fingers gently slid down my zipper and her hand started to rub up and down my crotch. I was rock hard and I knew she could feel my cock bulging inside my panties.

Jessica lifted herself off of me and edged downwards, pulling off my jeans, revealing my pretty blue panties which were covering my hard cock; which, by that time was poking out of the top of them. I could see Jessica's hard dick through her see-through panties, sticking straight up, pressed against her skin and I was more than enthralled about being with her, than I was before.

Jessica came to rest on top of me, right in between my legs. Her warm body pressed up against mine, as I felt my hard dick being pressed between us. I could feel her hard cock on top of mine as she began to slowly pump back and forth, as if she was dry humping me. I raised my legs up a bit further resting them at her sides. I wanted her to be in me. I wanted our panties off. I wanted her to be fucking me like this. I wanted to feel her thrusting back and forth deep inside of me. I wanted her to be my first anal experience. And I wanted her to cum in me.

The passion of the moment overcame me and I rolled Jessica off of me and onto her back. I laid on top of her for just a few seconds, until I started kissing my way down her body. I stopped to caress her tits a bit, but my goal, my want and my desire, was that dick. When I got to her panty line, I grabbed both sides of her hot see-through black panties and slid the down. Jessica opened her legs up, as I was looking up and down her body, with her hot, sexy, hard cock sticking up in the air.

I gently and slowly kissed my way up her legs, making sure I got the overly sensitive areas inside of her thighs. I put Jessica's hard cock in my mouth and slowly slid it all the way in. All the way down my throat as far as I could go. I wanted to suck it into me. I wanted to be everything she has ever wanted and I wanted this to be the best blow job and fuck she has ever had.

I slowly bobbed up and down on her shaft, getting her cock soaking wet with my saliva. I had long come to terms with the fact that I liked sucking dick, but with hers it was a whole new dimension of desire. I wanted to suck it all night long. All day long. Anytime she wanted it sucked, I would suck it. I wanted her to be pleasured beyond belief. I slurped up and down on her, making deep eye contact as I kept ramming it in and out of her mouth. Her beautiful light-colored skin, her little tits, with perfect nipples, her pretty face and beautiful ginger hair made this one of the most erotic nights of my life.

I felt my cock pulsing. I felt feelings inside of me, I had never had before and I wanted her in me. I needed to be fucked and I needed her to fulfill that desire.

I pulled Jessica's cock from my mouth and edged off of the bed. I walked over to my dresser where I kept my toys and my lube, grabbing the bottle from the drawer. I shook the bottle in my hand as I walked back to the bed. I saw Jessica lying there naked, hard, awaiting my return with a big ole smile on her face.

I stopped as I reached the edge of my bed and slid my panties down and off. My cock popped out like a spring, hard, full, plump and raring to go. I edged back down onto the bed, where I had been and got right back down, face to face, with her hard dick. I softly kissed the tip, licked up and down the shaft and just pleasured her for a while, making sure she stayed hard and ready. I popped the lube top open and poured a good amount onto my left palm. I used it to slowly stroke Jessica's hard cock, up and down, slowly making it overly slippery and wet. I watched myself giving her a long-wet hand job, just seeing the pleasure on her face and in her eyes as we started at each other.

But I couldn't take it anymore I needed her in me. I put Jessica's cock back into my mouth and felt the cool smooth lube along her shaft as I started sucking her cock again. I reached behind me and was rubbing my asshole with my lubed fingers, preparing myself for penetration. I slid a finger in and moved it in and out a few times, just making sure I was ready. The nerves hit hard and the stomach was turning, but I wanted her.

I raised my body up, pulling her cock from my mouth as I edged on top of her. I climbed over her cock and was just in the position of lining up, as I squirted a bit more lube on my hand. I reached behind me and soaked my asshole with it and then grabbed her cock stroking her harder and longer getting her slippery wet. Jessica and I both knew neither of us were unsafe; since I had never been penetrated by anyone before and her only in long-term safe situations, we weren't overly concerned about protection.

I grabbed a hold of her cock and started to sit down on it, lining it up. I felt the tip at my asshole and I started to push down. I missed the correct angle the first time; but on the second try I felt Jessica's cock slide right into me. I gasped for air, as her long sexy cock started to slide deep inside of me. I got so hard, and my skin stretched so tightly on my cock, I thought I had grown an inch longer. I took Jessica's cock all the way in, just as I was starting to turn and make my upwards momentum. Her hands resting on top of my thighs as I started riding her slowly and deeply as I raised up, then down, feeling her hard cock sliding in and out of me.

My mouth wide open, breathing very shallow, as I was sliding up and down on her hard cock. Nothing I had ever experimented with; the toys, the dildo's, the butt plugs, Strap-on's and all the videos, were nothing even close, or ever as stimulating as it was being here riding Jessica's cock. I was beyond aroused. Beyond fascinated and beyond pleasured. I was riding up and down on her dick feeling it sliding in and out of me, as I looked down on her. Her hips shook, swayed and thrusted upwards at times ramming her cock deep inside of me. I was hoping I was doing this right since all my experience had been with inanimate objects. But apparently, I was doing okay, because she was still hard, still thrusting into me and had that look of absolutely pleasure in her eyes as I continued bouncing up and down on her hard cock.

My cock started flapping up and down as I started to get a faster momentum and rhythm. Jessica, would occasionally, reach out and cup my balls or stroke my cock as I continued bounding up and down on her. It was INCREIBLE!!! I had a dick in me! I was fucking loving it! My first real dick, buried deep inside of me, pleasuring me. And I wanted to feel it more and more.

I wanted her to roll me over and put me on my back and ram that cock deep into my ass. I wanted her to nail me from behind, pumping and thrusting into me like never before. I wanted her to shoot her load all over my balls. On my chest, on my back, but most importantly up my ass.

"OH, Fuck Jessica. Your cock is amazing". I groaned out as I continued to ride her.

"You like that dick in your ass?" She asked.

"Yes. Yes, I do." I replied.

And I did. It felt amazing. It felt exciting, it felt erotic. It felt taboo and I was in love with it!! Period.

I knew who I was and where I wanted to be. I was all woman, and I wanted cock! Forever! Period. Dick. Dick. Dick!!! Period.

I continued riding up and down on Jessica's throbbing cock. Felling it sliding in and out of my ass, while my cock stayed rock hard and ready to explode.

I must have ridden her for the better part of ten minutes. Time to time, I would lean down and we would kiss deeply as she would be the one thrusting it in and out of my ass, only for me to return upwards and take it as deep as I could by my momentum. As fast as I could and as hard as I could, as I stayed erect and overly excited to be getting fucked. Jessica's beautiful face and gorgeous eyes starred deeply into mine as we continued making love.

"Baby you're going to make me cum." She blurted out as I was riding her hard cock

"Fucking cum in me baby." Was my reply.

I was overly excited and arouse to hear that and it made me want this even more. I wanted her to cum. I wanted to know I was the one that made her get off. I wanted to feel her blasting her load in my ass, while I came from it.

I started riding her harder and deeper. Jessica's hips started thrusting upwards, as her head leaned backwards rocking from side to side. Her hands rubbing every bit of me, but also rubbing every bit of her.

"Fucking cum baby! Fucking cum!" Kept flying from my lips as I bounced up and down on her hard cock.

"I'm gonna cum," she squealed out. "I'm gonna cum."

Jessica started raising her hips so high off the mattress ramming her cock even deeper into my ass, as I was moving up and down, that I felt like there was a street light post sliding in and out of me. I was so overwhelmed and feeling pleasures in places I had never felt before. I was so hard, stroking myself as she was thrusting that cock deep inside of me, bringing herself to orgasm.

"I'm gonna cum!" I cried out as my hand stroked my dick hard and as fast as she was pumping me from below.

"I'm cumming!" She cried out, as I felt her cock starting to thrust and pulse deep inside of me.

"Holy fuck, You're cumming in me." I cried out, as I felt her cock shooting her cum deep inside of my me.

The absolute pleasure and passion of her cumming in my ass sent me into overload; and before I could even stroke myself further, I started shooting my cum all over her stomach and chest. It was flying everywhere. With every thrust up and down, I was shooting cum in all directions.

"Holy fuck!" I cried out, as I was blasting my load into the air, as she was blasting her load deep into my ass.

Jessica pulled my body down on top or her, our faces met and we entered into a deep passionate kiss. Her hips still lightly thrusting up and down as she was expelling the last bit of her cum deep in my ass. My cock still lightly pulsing and oozing the last bit out of the tip.

I want more. I want to fuck her more, I thought to myself. I want to suck her cock. I want a line of cocks here now, waiting to fuck my tight as. Holy FUCK! This was amazing.

Jessica pulled from our kiss, looking me deeply in the eye and whispered, "That was amazing!"

And it was. But she had no idea how amazing it was for me.

I stayed on top of her for a long time, just feeling her cock inside of me, feeling the wetness of the lube and her cum slowly seeping out of me. Feeling what it was like to be coming down after orgasm, with a cock deep inside of you after being fucked, while the cock slowly recedes. Feeling the sweat of your bodies as you rest chest to chest. Knowing you want more. You want this forever and you want more!

Before the night was over, Jessica and I had sex again. This time, we just sucked each other off in a long side by side 69, until she came deep down my throat, and I into hers.

That night changed me. I knew from that moment on, it was always going to be wanting dick. Hopefully hers!

I knew I wanted to be all the woman I could be. I wanted to get tits. I wanted to have my dick cut off an get a pussy. But in all reality, I liked my dick and still wanted it! I knew I was going to suck dick and be fucked for the rest of my life. I knew it! I accepted it! And I wanted it! I was never turning back.

Over the next few months Jessica and I became a deep loving couple, developing our relationship even more. I started HRT and was becoming Monica even more. I came out to some people. To some friends and even to some co-workers. I had Jessica at my side. I had her faith, her love and her support.

But I had to come out completely. I couldn't be Matthew anymore. It was time to take the biggest step I had to take. Coming out to my parents and after a bit of time, asking Jessica to marry me.

I'll tell you all about it in the next chapter.

To be Continued...