Mikes First Transgendered Pt. 05

Mike first transexual experience part 5

Please read 1 -- 4 before this one.

I awoke the next morning after finally experiencing anal sex. Life wasn't much different that day, the birds chirped, the sun was out, but I know in my heart I was wanting cock more than pussy. I could still smell Sara's perfume on my sheets and I wanted her lying next to me. I grabbed my phone and texted her a good morning message.

Sara replied, "Good morning love, I hope you slept well."

"I did 😊", I replied.

"Sara, what do you have planned for today?" I Asked.

"Just working later afternoon. Why, what do you have in mind?" Sara replied.

I told her, "I really want you here and thought maybe we could spend the day together."

Sara wrote, "That's a great idea but I have to work, don't you?"

"I do but I could always call in sick." I reply.

Sara writes back, "You know what, I would love a day off and I would love to spend the entire day with you. If you want to call in sick, I'll call in sick and I'll come by you."

Sara continues, "I'll leave here at my usual time, I'll pick up some lunch for us and I'll spent the entire day with you. Does that work?"

"Yes, it does," I reply.

After some further back and forth plans are set in stone, lunch is agreed upon and I get excited knowing she's coming over to spend the day with me.

** What I haven't bother telling you readers through all of this is...Sara lives with a gentleman about 30 years older than her. For all intents and purposes, he was her mentor, lover and more importantly her sugar daddy. He helped her through her transition, paid for her augmentation, helped her becoming the woman she always felt she was. He has given her a place to live, her car and for a long time was her significant other. However, as the years have gone by and due to some prevailing health issues, he has not been there for her the way he used to be. Sara has always stood by his side and will probably never leave him unless she knows it's forever. And I believe that has stopped her from entering fully into any relationship that may have been more beneficial to her. I know she can never spend the night, or live here with me. But I have chosen to accept that when she told me about him at the beginning of all of this. **

Sara arrives at my house at about 1:00 P.M. She is dressed as if she's going to work, with her skirt, pantyhose, high heels and business casual shirt. Her long coat hiding her hips and breasts as I watch her walk up my walkway. She is carrying food from a restaurant and I greet her at my door. I give her a warm soft kiss on her lips as she enters in and take the food from her hands. Sara takes off her coat and kicks her heels off. We sit at my island nook and eat out lunch, just chatting and enjoying each other's company. After we eat, Sara asks me, "What do you want to do today?"

I reply, "I don't care. We could go out, we could go shopping, we could go to a movie, we could just stay here. Whatever you like. I'm just glad we have all day to spend together."

Sara says, "I'm a little leery about being out in public, because I called in sick. But I don't mind just relaxing here with you."

We decide to just cuddle in my bed and watch a movie. We head up to my bedroom and Sara takes of her skirt and shirt and slides out of her pantyhose. Her exquisite body adorned in only her black panties and bra with her bulge showing. I find a movie for us to watch as she climbs into my bed and slides under the covers. After getting situated I climb into bed next to her, we adjust the pillows and she places her head on my chest and cuddles up next to me. My arm is wrapped around her from behind and I am softly rubbing up and down her shoulder and arm as we watch our movie. Her perfume is softly filling my senses and her hair is resting along the side of my face. We spend our afternoon just cuddling up in each other's arms, switching positions when needed finishing up the movie we are watching.

I must tell you that lying there with her was incredible. I felt so comfortable and complete as we lay together. If I could have made things more permanent with her, I would have. I never would have imagined taking an afternoon lying in bed with my shemale lover, knowing her dick was the most important thing to me (at the time) and that I had no problem spending more and more time with her, sleeping with her and trusting in a homosexual relationship. I started wondering to myself was it her? Was it that she was (in all essence) a female, with that something extra? Was it her dick and the fact that I had always considered myself Bi-Sexual (maybe more) and wanting that dick on a more permanent basis? Was I just cock crazy, because I had never had a man before? Did I want to make this permanent and ask her to leave her significant other? Was I just experiencing something new and exciting, especially after a bad marriage and a bad rebound girlfriend? Or was I coming out and finally realizing I was gay and was going to have dick the rest of my life?

As the movie was ending, we laid spooning with my arms wrapped around her. My hand was on her breast and I could feel all the excitement I always had being with her. I began softly kissing the back of her neck, along her cheek and her ear. Sara moaned lightly grabbing my hand that was on her breast pulling my arms more tightly around her. I could feel my dick starting to get harder. Sara, leaned her head back towards me and our lips met. Our kiss was soft and closed lipped at first, but the turned into a French kiss. Out tongues swirled around each other's mouth as she leaned further back towards me. Sara adjected herself and rolled onto her back as I leaned further onto her side. Her kiss was incredible and I could have spent all day just kissing her like this. My dick became fully erect as we softly and slowly made out. I cupped Sara's breast with my hand and caressed her breast over her bra, getting her tuned on. Sara, pulled from out kiss, looked me in the eye and said, "I can't get enough of you Mike."

I smiled at her and said, "I feel the same Sara."

Our passions exploded as I slid my hand inside Sara's bra and caress her breast. I pull my arm out from underneath her and ran my fingers through her hair. My heart is feeling warm and fulfilled as we lay there in deep kiss. I pull my hand from her bra and start rubbing up and down her stomach, slowly making my way down to her crotch. I feel the soft silkiness of her panties as my hand reaches her crotch. Her cock partially hard and bugling in her panties. I rub up and down her feeling her shaft and her balls tucked so neatly inside her panties. After many of soft slow strokes, I slide my hands deep down inside her panties and grab a hold of her hard shaft. I pulled her dick upright and slowly start stoking her. Sara moans in pleasure. We continue kissing deeply as her hands run along the side of my face. My dick is rock hard in my pants, but in my mind. I'm not worried about myself; I just want to play with her dick. I want to suck her until she's soaking wet with saliva, rock hard and slide her dick deeply back into my ass. I slowly stroke her cock feeling her hard boner in my hand, feeling her skin sliding in and out of my fingers, bringing her closer and closer to orgasm. I break from out kiss, roll backwards, reach into my night table drawer and pull the lube out. I open the top and pour a lot on my hand. I lean back towards Sara, begin kissing her and put my hand back on her cock. I slide my hand up and down the backside of her hard cock, and cup around her balls, getting every inch of her soaking wet with lube. I rub and caress her balls for a minute, until I slowly slide back up and grab a hold of her firm cock. I slide my hand up and down it making her wetter and harder. I slowly start jacking her off, hearing the soft squishy sounds of lube on my hands and on her cock.

Sara is deeply turned on and is breathing heavier and moaning. Sara reaches both of her hands to her hips, grabs a hold of her panties, raises her hips and ass and slides her panties down. Using her legs to kick them off completely. Sara rolls towards me and reaches for my pants, I feel her unbutton and unzip my jeans and rams her hand down into my pants. She grabs a hold of my firm cock and starts stroking me as I am stroking her. Our kisses fade in and out, our lips touch, our noses rub and we stare deeply into each other's eyes. I take my hand from her dick, lift my hips and slide my pants down, followed by my underwear. As I get re-situated, Sara and I go back to kissing softly while giving each other hand jobs.

I whisper, "Sara I want you in me."

Without hesitation, Sara starts pulling me on top of her. I slide up and over her body, not breaking our kiss. I feel her hard cock resting on my ass cheek. Sara grabs the lube and pours some on her hand. She reaches down and under me and starts rubbing my asshole with her lubed fingers. The sensations she is sending through my body are immense and I want her to continue pleasing my ass. I feel her grab her cock and line it up with my asshole, I push done and feel her start sliding into me. My mouth opens with pleasure as I let out a soft moan. I feel her cock sliding into me, just like last night. I slowly start raising and lowering taking it deeper with each thrust. She is deep inside again and I FUCKING LOVE IT.

"OMG Sara," I moan.

I lean forward and pull Sara's bra straps down her shoulders, pulling the cups down with my motion. I lean into her for a deep kiss as my hand cups her exposed breasts. I feel her lifting her hips up and down, sliding her big cock inside me. In my head I think, we should have put on a condom, but I know she's clean and I want her cock in me without a barrier. I sit back upwards and begin bounding up and down on her dick like I should be. The newly discovered gay boy in me is learning how to ride cock and ride it well. I continue my up and down motion just enjoying every minute of her cock inside me. My cock flapping up and down as I ride her. The bed squeaking and creaking as I ride her deeply. Sara's hand grabs a hold of my cock and she is stroking me as I ride her. I am rock hard and could cum at any minute. After a while my legs start to get tired and I want to try something different. I stop my motion and say, "Sara, fuck me from behind."

I climb off of her, feeling her cock slide out of me. She starts to get up, rips her bra off and gets on her knees. Sara climbs in behind me, adjusts my height and puts the tip of her cock right at my asshole. She grabs my hips and pushes forward as I feel her slide back into me. I gasp in pleasure and pain. I lean my head down onto my pillow, as her hands pull my hips backwards as she slides her dick forwards into me. After slowly getting it all the way inside me and slowly pumping back and forth, Sara quickens her pace, fucking me like the little slut I am. My mouth wide open and high-pitched moans squeak out of me as I feel her pounding my ass. The feeling of her cock deep inside me from this angle is more than I can handle. I start screaming out, "Don't stop Sara, don't stop."

My balls are swaying back and forth and my cock is so fucking hard. I can't believe how much I am enjoying this. Sara is breathing hard as she is pumping her cock in and out of me. She is incredible and I can't get enough. Without even touching myself, I feel I'm getting closer to orgasm. She is hitting spaces deep inside me I have never felt before. In my mind I was thinking if this is what gay sex feels like, I want this al the time. Just being on my knees with a big dick up my ass fucking me like a sissy girl is the way I want it. I moan out, "Sara your cock is perfect!"

Sara starts moaning aloud, "Mike I'm going to cum."

I answer, "Cum in me Sara, cum in me.'

As Sara start pumping me harder, she is actually bringing me close to orgasm. I feel pleasures running through my body like I've never felt before. My dick is pulsing and throbbing ready to explode.

I start screaming out loud, "Sara, I'm going to cum, Oh My Fucking God, I'm going to cum."

Sara pushes hard a deep a few more times until I hear her screaming, "I'm cumming, I'm cumming!"

I felt her cock start thrusting and start shooting her cum deep inside my ass. The pleasure overload reaches my mind, my heart and my cock and before I can even touch my dick, I feel myself start cumming. My dick is shooting out cum, all over the bed as I feel her big dick releasing her cum deep inside me. I am squirting everywhere as she is squirting deep in me at the same time. My legs shaking, my heart thumping, my body quivering. My cock releasing the last drops of my cum onto the bed as she is resting her cock deep inside my ass. "OMG Sara, you're still cumming!"

My body quivers from the pleasure. I have never known such a feeling and I can't get enough of this. I want cock all the time! I wanted to beg her to keep going and just keep ramming her cock in and out of me until she cums again. But I know she spent a lot of sperm in my ass and I just came all over the bed. I believe we both needed a few minutes to recharge before going again. Sara leans over onto my back and wraps her arms around me. We are both trying to catch our breaths and finish our powerful orgasm. Her cock is still buried deep inside me along with all of her hot sticky load. I giggle and tell her, "I came all over the bed."

Sara giggles and says, "Well we will have to avoid the wet spot."

We stayed in that position for a while until she finally pulled her cock out of my ass. I laid down flat and she laid down next to me. We both rested and cuddled in each other's arms. After a nice long nap, we started fooling around again. We kissed and hugged and touched getting ourselves aroused again. I wanted to be in her. My dick was rock hard and I was ready to penetrate a man; a Shemale. Sara was ready too. She got on her knees and I slid in behind her. I was so nervous, I was shaking. I looked down to see her hot asshole and balls staring at me. I lined up, poured some lube on the spot and slowly slid my cock deep inside her ass. Sara moaned with pleasure as I entered her. I pumped back and forth with the hardest boner I think I ever had. I was so excited that it took me all of about 2 minutes to cum deep inside her. I couldn't believe it! It was ABSOLUTELY AMAZING! I have never gotten off so fast and surely never got off fucking a "man" in the ass. But I fucking loved it. It was an incredible experience to fuck a shemale in the ass. It surely wasn't the last time...

Sara stayed until 11 o'clock that night and don't believe for a minute that we weren't naked the rest of the day. We ate dinner in bed naked, we showered together and we even watched another movie naked. Before she left that day, I had been on the receiving end of another round of anal sex and gave her a long-wet blow job after our shower. During the course of that day, Sara came in my ass twice and down my throat once. I came on the bed once, in her ass once and in her mouth once. And I wish we could have gone / done more.

Before Sara left, I asked her to consider making this between us more permanent. I told her, "I know your situation and I am willing to help you get out on your own, so we can be together."

Sara said; "I will think about it, but it's a hard situation for me without him, and him without me."

After she left, I spent a lot of time thinking. I was ready to come out. I was ready to tell everyone. And to be honest I was ready to spend a great amount of time only having dick and not pussy. I didn't care if I was the top or bottom or both, I was ready to be gay; or at least Bi-Sexual and in a homosexual relationship and I didn't' care who knew.

Sara and I did spend many other afternoons and late evenings after work together. We did just about everything we could as a couple and sexually. I fucked her many more times and of course - since I absolutely loved it -- I got fucked even more by her. I must have swallowed a gallon of cum from all the blow jobs I gave her. And I would have swallowed a gallon more or been the bottom every time, because I loved her that much and loved her dick that much. Looking back, I was absolutely in love with her and wanted to make her my on-going girlfriend. But unfortunately, a few months later Sara and I parted ways, not for lack of love, but due to her commitments and having to take care of someone who had taken care of her for years.

I never did blame her, just wished she would have considered me -- or us - more.

But that wasn't the end of my transgendered and boy relationships. I'll tell you about some of them as we continue with these stories.

On to the next chapter...