Mikes First Transgendered Pt. 04

It was a cold rainy night in October and I was just leaving work about 8:00 P.M. when my phone rang. It was Sara. I hadn't seen her in almost two weeks, due to our schedules clashing, so when I saw it was her calling, I was excited. As I got in my car, I answered her call.

Sara said, "I am leaving the restaurant early because we are slow and I wanted to see what you're up to?"

I told her, "I am just leaving work and was heading home." I told Sara, "If you want to come by, I'd love to see you."

Sara said, "I was hoping you wanted to meet for a drink. I've had a long week and could use some company and decompress a bit."

I told her, "I know a bar not to far from where you're at and if you want, I'll meet you there for a drink.

Sara agreed and I started making my way there.

Sara was already inside the bar when I got there. We decided to sit in the back corner and just have a few glasses of wine. The place was practically empty, so I played some music on the Jukebox and just enjoyed spending time with her. We sat and talked for about and hour each having a couple glasses of wine. We sat solemnly, holding hands, laughing and truly enjoying a peaceful night together. Our conversations revolved around our lives, our passions, dreams and things we hoped for. It is always a turn on for me to be in public with her. Knowing that outwardly she looks like a normal average female, but underneath it all was a big cock. It just amazes me how many people couldn't tell she Trans and wouldn't even believe me if I told them. Yet, while I'm with her I enjoy her conversations, her intellect, her beauty and get aroused by what dangers between her legs. Hoping later I can be reaching down to find it. As the night drew to a close, I didn't want her to leave. I asked Sara, "Do you want to come back to my place to just relax a bit more before you head home?"

"Yes", she replied.

She followed me home driving through the pouring rain. After getting inside the front door, we were both drenched. I hung her coat up and offered her a towel to dry off. Sara and I stood in my kitchen talking, just passing the time as we opened up another bottle of wine. We had a few more glasses and just kept our conversation rolling. I was in awe of her. She was so smart, funny, sweet and sexy. There wasn't anything I didn't like about her and one thing I really did like!

We ventured into my room because she had asked me to play my guitar for her. Sara knew I was a bit of a musician and she wanted to hear me play. I played a bit for her as she just saw watching me, sipping her wine. I realized at that moment I was really falling for her. When I finished playing and embarrassing myself, I put my guitar back and sat on the edge of the bed next to her. Sara reached over and put her wine glass on my night table, turned back to me and with deep eye contact, leaned over and kissed me. It was soft, deep passionate kiss. Our tongues swirling around in each other's mouth slowly and softly. I could smell the sweet perfume on her neck and felt her hair alongside of my face. I was utterly attracted to her and wanted more of a relationship from her, besides our every other week visit.

I told Sara, "You know I am falling for you. I want you in my life more."

Sara smiled and said, "I want that too."

I had never been attracted to anyone with a penis, but I just couldn't get enough of her.

I got up on my knees climbing onto my bed trying not to break our kiss. Sara followed suit and we were both kneeling facing each other in a deep passionate kiss. Our arms wrapped around each other as our heads moved back and forth, our tongues releasing our passions. We pulled from our kiss, just starring deeply into each other's eyes. I felt Sara's hands on my ass. My hands on her face. I pulled her in for another kiss. I wanted her so bad. I was already hard and wanting her to take me. I pulled off my work shirt and my T-shirt from underneath. Sara's head lowered and she kissed her way down my chest, sucking on my nipples. Sara eased me down and onto my back and laid partially on top and on the side of me. We continued kissing and touching each other. I felt Sara's hand start rubbing up and down my chest, past my stomach and down to my crotch. Her hand making her way to my dick, rubbing me over my pants. I felt her pull at my belt, opening it up. She unbuttoned and unzip my Khakis. I felt her hand slide down into my underwear, grabbing a hold of my hard cock. Her hand softly stroking me as we continued our deep kissing.

Sara pulled from our kiss leaning upwards unbuttoning her shirt and taking it off. She unhooked her bra, exposing her plump tits. She leaned forward and over me and I sucked on her nipple while using my hand to caress and tease the other nipple. Sara pulled her tits away from my mouth and kissed her way down my chest and past my stomach. Sara pulled back my underwear letting my rock-hard cock free. Sara leaned down and softly kissed and teased the tip of my dick with her tongue as I laid back in pleasure. Her mouth engulfed my hard cock as I felt her warm wet mouth sliding up and down my shaft. I can hear her lightly moaning in pleasure as she sucked on my dick. I started to remove my pants and underwear as Sara kept slurping on my cock. After getting my pants off, I could see Sara was trying to remove her dress pants and panties from her legs. With a few thrusting, shaky moves, she finally got her clothes off. Sara lay next to me, almost curled in a ball sucking my cock. Her hand cupping and holding my balls. On occasion she'd use her hand in conjunction with her mouth stroking my cock making me more excited. I spread my legs apart more as I felt her fingers slide in between my ass cheeks, her fingers rubbing and swirling around my asshole. It was arousing and turning me on even more. Sara stopped sucking on my cock and climbed on top of me. Her breast pressing against my chest, her lips to mine, her hair in my face, her dick on top of mine.

I whispered to her; "I want you."

My hands slid up and down her back and across the top of her ass as we laid together in a heated make out session. Our naked bodies entwined with each other. At this point this was the most romantic sex her and I ever had.

Sara lifted herself off of me and edged forward. She pulled herself up and further on top of me practically sitting on my chest as she brought her hard cock to my face. I adjusted the pillow under my head and moved my head forward to put her hard cock in my mouth. I laid there bobbing back and forth sucking on her hard dick. Just the excitement and realization of watching her hard dick slide in and out of my mouth was intoxicating. My dick was rock hard. I wanted her to fuck me. I wanted her to take me. I wanted her to be in me. After working her big 7" cock for a few minutes, Sara climbed off of me and laid down next to me. I reached over to my night table, opened the drawer and removed a package of condoms and lube. I wanted her in me and I wanted her now! I slid down in-between Sara's legs lying flat down on my stomach. I opened the bottle of lube and poured some on my palm. I started slowly stroking Sara's cock with my hand. The lube made it so easy to slide up and down her dick. I just watched in awe as my wet hand slid up and down her big hard shaft, just watching myself stroke her was an amazing sight. I put her balls in my mouth and I just softly caressed them with my tongue as my hand continued working up and down her cock.

After getting her all lubed up, I put her cock back in my mouth. I used my lubed hand and fingers and started caressing my asshole making it wet and ready for cock. I slid a finger inside myself, just to get more lubed up and ready. I pulled away from Sara and sat on my knees. I opened the condom wrapper and rolled it out onto her hard dick. I climbed on top of her and placed the tip of her cock right at my asshole. I was so nervous, but yet so excited.

I told Sara, "I have never been fucked before, so be gentle with me."

Sara smiled as I started lowering myself onto her dick. After a few misses, I finally felt her break through and begin to penetrate me. The pressure was immense and a bit painful. None of my dildo's or toys, were as big as her, so this was going to be the biggest thing ever enter my ass. The excitement was more than I imagined, but the discomfort of this big cock sliding into me, was startling. I finally felt her slide all the way in me. Sara let out a deep groan, as I took every bit of her cock inside me. I slowly started rising up and then down, just letting my ass adjust to her size and depth. My heart raced. I never would have imagined I would be here losing my anal virginity to her. The soft glowing light in my room made it more seductive.

After finally getting a bit more adjusted, I started riding her the best I could. I leaned forward and placed my hands on her tits as I rose up and down on her throbbing cock. I could feel her deep inside me hitting places never touched before. I was in absolute pleasure. I have waited so long for a cock to be inside me, now I am finally getting it. I picked up my pace as Sara started softly thrusting her hips up and down slightly to help slide deep inside me. I reached back and grabbing the lube purring more in between my ass cheeks so I can lube her dick up more. While my hand was back there, I cupped and caressed her balls and could feel her shaft as it slid in and out of me. I leaned down and kissed her passionately as my up and down motion continued. We were wrapped up into each other as I continued feeling her cock sliding in an out of me. I started riding her faster and deeper letting that big cock deeper into me. I wasn't completely hard anymore, but I didn't care, I was being fucked!!!!

I was enamored as I rode her. The feeling of her dick in my ass was exhilarating. I wanted to do it right. I wanted to please her. I wanted to be the reason she was going to cum. I was getting to know what it felt like to have a real cock deep inside of me. I could hear the squishy sounds of the lube on the condom as it slid in and out of me. My mouth was wide open, high pitched moans emanating from inside me, my dick flapping up and down, Sara's hands on my body. I had fucked a lot of girls in the ass and now I knew the pleasure they had received. I was so turned on, so happy, so free. I was so excited, I was being fucked, I had a dick in me and I fucking loved it!

My legs trembled with every up and down thrust, my cock flapping up and down as I rode her hard. Looking down seeing Sara's beautiful face so aroused, seeing her sexy tits in motion with me, while riding her cock was pleasure enough. I don't know how long I had been riding her, but I was loving the feeling of getting more familiar with taking it in the ass. I wanted to get her off. I wanted to make her cum deep in my ass. I bounced up and down hard taking every inch of her deep inside me. The bed was shaking and squeaking as I bounced up and down on that cock.

As I rode her, I started moaning out, "I love dick Sara, I love your dick. OMG, I love your dick."

And I did. I was instantly and overwhelmingly addicted to cock. I had waited my whole life for this and now I couldn't get enough. My moans and whimpers heightened with each thrust. Sara started thrusting her hips upwards harder and harder each time I was coming down. Her cock slamming in and out of me. "OMG Sara," I screamed... "OMG Fucking God."

As my initial fears and concerns dissipate and I started enjoying every minute of this, I started to get aroused again. My dick was getting hard again and the pleasure was churning throughout my whole body. Never would I have imagined being with a shemale, let alone anyone with a dick and now I was riding her big cock and loving the exhilaration of being fucked in my tight virgin ass. Sara reached down and started stroking my cock as I bounced up and down on her making me more enthralled with this moment. Her free hand was pulling at and twisting my nipples. I leaned down face to face with her again. I started kissing her, swirling my tongue inside her mouth, sliding back and forth feeling her cock slide in and out at a different angle. Sara slowed my momentum and held me in one spot. She began raising and lowering her hips, sliding her cock in and out of me. I was no longer in control, she was! The feeling made me lose all abilities, I couldn't think, I couldn't kiss, I couldn't breathe, I couldn't even focus on anything but feeling that cock slide in and out of me. She slowed her pace and just softly and slowly slid in and out of me as our foreheads rested against each other, noses touching, feeling each other breathe. I knew right there what it felt like to be a woman and having your man's cock slide in and out of your wet pussy. I was falling in love. All my gay desires were coming true, I was becoming cock crazy.

Sara assisted me off of her. My legs were like rubber as she laid me down on my back. My breathing fast and erratic, my head spinning. As Sara climbed on top of me, I spread my legs and felt her dick, rock hard, hit the top of my dick. We kissed deeply and passionately as my asshole throbbed from being fucked. Sara lifted my legs up a bit and slid down lower, she grabbed a hold of her cock and was trying to line up with my asshole. I assisted her in getting the right angle and location and she pushed herself back into me. I raised my legs further up along her sides and starred into her eyes deeply as she began sliding her dick in and out of my ass. Sara's arms extended out holding her up as she started pumping me faster and faster. Her tits swung back and forth with her momentum. My legs still pinned to her side as I felt her penetrating deep. I knew at that moment I wanted her cock more than anything. I needed this feeling, this love, this penetration. All my fantasies were coming true.

I knew she was getting close to cumming and I wanted her to explode in me. "Fuck me Sara," I blurted out.

I pulled her in for a kiss, mouthing the words, "Cum in me baby, cum in me."

Sara lifted herself back up and quickened her pace. She was thrusting her cock as deep and as far into me as she could. Within seconds Sara started moaning, "I'm going to cum, I'm going to cum."

With that, her thrusts became faster and faster, my pulse quickened, her breathing increased. She pumped me hard and deep until she thrust her head and chest back and pushed herself deep within me, making me scream in pleasure. Sara was cumming in me. OMG FUCKING GOD! Sara was cumming in me!

I could feel her body quiver as she was releasing her load in my ass. I wished she was bareback so I can feel her cum deep inside me!

After a few slower deep pumps, Sara eventually expelled every drop inside me. Her body collapsed onto mine. Her breathing heavy, her skin wet with sweat. She laid on top of me for a few minutes, her cock still buried deep inside me. I wrapped my arms around her, holding her kissing the top of her head. After a few minutes she pulled herself out of me letting herself free. She sat up on her knees and slid the condom off as her breathing slowed. My body and asshole still pulsing, legs quivering as I was recovering from this fucking. It took both of us a few minutes to come back to reality and settle down.

Sara knew I hadn't cum yet, so she started to used her hands to get me aroused again. As she slowly pulled on my limp dick, trying to get me hard, she smiled and said, "It's your turn."

Sara leaned over and grabbed the bottle of lube and poured some all over my dick and balls. She proceeded to rub me and caress me, playing with me, arousing me. She slowly worked my cock back to a full erection and was giving a long, slow, soft sexy hand job. I was just lying there in pleasure watching her stroke my cock, seeing her dick between her legs, her tits hanging and wanting her to make me cum. Just as I got close to orgasm, Sara wrapped her mouth around my cock again and sucked me until I exploded in her mouth. She moaned in pleasure as every drop of my cum passed down her throat. After I finished cumming, Sara climbed up next to me and cuddled in my arms. We kissed deeply for a while and talked about my first anal experience. My body was still quivering and shaking from being fucked hard. What a way; and a what person to lose my anal virginity with.

Sara asked me, "Did you like your first time? Did you like riding my cock?"

I told her, "Yes, I was a little nervous at first, but I wanted you to fuck me so bad." I furthered by saying, "I loved it and couldn't wait to do it again."

Sara asked me, "Do you think you like boys more than girls now?"

I replied, "I think I like both equally, but right now I am liking cock more."

Sara asked me, "One night do you want to fuck me?"

"Yes, I'd like to try", I replied.

She smiled and said, "Good, I was hoping you would."

A while later Sara had to make her way home; I knew she had to leave but I wanted her to stay. I wanted to make love to her again. I wanted to make her cum again. I wanted to feel her deep inside me.

I watched her as she got dressed. I watched her put that big cock back in her panties, put her bra back on, slide her pants up and put her shirt back on. When Sara finished dressing, she came over to me, placed a long slow soft kiss on my lips and said, "Stay in bed, I'll let myself out."

As I heard my front door shut, I ran to my window and watched her walk to her car. I was hoping she would turn around and come back in. I almost texted her and told her to come back. But it was late and she had a long drive home.

As I climbed back into bed, I laid there in absolute amazement -- almost disbelief - of what just happened. I had to tell someone about this. I wanted to scream to the world "I finally got fucked, I got anal sex." I grabbed my phone and texted an old (girl) friend. During the course of our conversation, I told her about Sara and our first few oral sex experiences and how I lost my anal virginity tonight. She did ask a lot of questions and was surprised I would be experiencing homosexual sex, but in the end, she was happy for me.

As my night concluded my thoughts drifted off to other close friends who would never expect this. Knowing they'd never know the feeling, fulfillment and excitement of bouncing up and down on a big dick. Knowing when I saw them even though I seemed like I hadn't changed. But knowing in my head that I was changing. That I'd know my spicy, erotic, nasty secret of being in a homosexual relationship, enjoying cock.

Knowing they'd never know the pleasure of getting off while sucking cock and the anticipation of wanting to play with cock again.

And to my co-workers who would ask me tomorrow - what did I do after work last night -- replying to them "nothing", but knowing I got fucked in the ass hard by a hot sexy shemale. Knowing I liked cock more than pussy (at that moment anyway). Knowing I had "taken it in the ass" and fucking loved it. Knowing I wanted to do it again and wanted to fuck her in the ass. Knowing they'd never know that late last night I was in bed sucking and riding my girlfriend's cock. That was all part of the turn on. The secret, the desires, the passion of it all.

As I dozed off my body was still reeling form being fucked. But I fell asleep peacefully, naked, spent and satisfied with what had happened.

I couldn't wait for her next visit...