1st time with a Transwoman

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1st time with a Transwoman
My first time with a transwoman was a very unique experience I must say. Having explored my options on the internet wasn’t an easy one. I was nervous and curious about my first experience having sex with a transwoman. I only had sex with biological women throughout my entire sexual life and this was a new experience for me. I checked for several months on Backpage and Craigslist on the dating classifieds ads for transwoman.

What I was looking for is an mature erotic, sexy and beautiful transwoman. I wanted my experience to be about me, pleasured like I imagined and what I fantasize in my wildest dreams and thoughts.

I came across a likely candidate to be my first experience her name was Lilith a beautiful Milf transwoman in Seattle area. We set up a time and date on 5/14/2014 @11pm. It had to be late do to our work schedules. I text her while arriving at 10:55 pm to let her know I was at her residence. I waited by the front door of her apartment entrance for her to let me inside. I waited just over 2 minutes and nervously pacing around until I saw this beautiful transwoman in a yellow dress like a pin-up model, heels to match, smile that was warming to my heart, blonde hair in pigtails, finger nails done up professionally and a runway model walk. She open the building door and asked my if my name was J. I studder by the look of her beauty and said, yes. She then extended her hand towards me. I reached and touched her soft hand, taking me into her apartment. As I walked through the door I was greeted by the sweet smell of lavender and jasmine in the air. Her pad was decorated with rock and roll memorabilia with five electric guitars. I was like dang, she right up my avenue with rock and roll and clean deck out pad. After a few minutes with the meet and greet I sat in a lounge chair in the living room and had a beer she’d offered me from her fridge. We chatted a bit to break more of the ice and then she kneeled in between my legs while I drank my beer rubbing on my thighs and chest. My Cock was already standing at attention when I grabbed her soft hand canlı kaçak bahis on my way into her apartment. As she began to rub on my thighs getting closer to my Cock as it throbbed inside my khakis. She noticed precum soaking my khakis and lick my pants to taste my sweet nectar from my loins. I told her that I never wear underwear, smiling at me..I thought to myself this so fucking HOT and the way she looked at me with those pretty blue-green eyes. I was so turned on and amazed at the eroticism and sensuality this woman was showing me. She then unzipped my khakis and thrusts my Cock into her eager wet mouth. Sucking gently and licking the shaft with the tip of her tongue. At this point I was in ecstasy and drawn into the lust between us both. I moaned in pleasure with every motion of her mouth upon my Cock. She was nonstop for several minutes enjoying my sweet precum. Looking into my eyes for approval that I was pleasured beyond measure. Then I took off my khakis and shirt, drank the rest of my beer when she suck my Cock for several more minutes.
Knowing I was ready, she lead me into her bedroom that was decorated all girly and with all kinds of high heel shoes on multiple shelves. Her bed was soft and yet firm the kind of bed to have great passionate sex and yet get a good nights rest with silk sheets. I laid on her bed while she enjoyed my Cock even more. Telling me she could suck me for hours because I tasted so fucking amazing. I smiled at her and she licked my Cock and said, I want you inside me J. She bent over the bed. I hopped off quickly and stood behind her smooth and firm ass. Spanked her ass cheeks with my hands hearing her whimper from every hit. Then I kissed, licked and nibbled on her cheeks and legs slow, caressing her silky smooth legs.

Now it was time for me to feel her from the inside with my throbbing Cock. I grabbed a magnum condom for my khakis and began to opening it. She said, wait let me do that for you honey. Again I was surprised and felt so like a King with my special hand maiden. She slipped my condom on the head of my Cock and began sucking casino firmalari and pushing it all the way on to its shaft with her mouth. I was a amazed again by her talent and attention to detail servicing me to the fullest. She then grabbed lube from the bed in a pink bottle and squeezed some in her right hand and began massaging some on my Cock, then her inviting pussyhole. She laid on her stomach bend on the bed with her legs spread just a little with her knees bent slightly. I began too rub my Cock on her tight hole. Then she asked me to go slowly seeing l that she hadn’t had a big Cock in such a long time. I took it slow sliding just the tip of my Cock inside her and then pulling it out. Feeling her tight hole grip my Cock like silky smooth velvet, working it inside her a little at a time, hear her whimper and moan with sounds of pleasure with every thrusts. Making it inside her hole of pleasure halfway teasing her and feeling her grab my ass pull me deeper inside her. I grabbed her hips and pulled her tight pussy all the way on my Cock thrusting slowly, feeling her pussy hole becoming wetter with every thrusts. She felt so amazing wrapped around my Cock. I almost popped my load within minutes of enjoying her. But I kept on going holding out till it builds up even more so. Feeling her tight hole wrapped around me was such and amazing feel. I never thought having sex with a transwoman could be so pleasurable. I stopped and pulled out my Cock and held in my urge to cum. My legs were shaking from the amazing pleasure I was experiencing. She turned her head and asked me if I’d cum and I said no, almost. She said, I made her cum so many times. Not knowing it was possible from analsex and my first time. I knew I would want more and more of this erotic experience.

After 15 minutes of chatting and cuddling with Lilith, she began stroking my Cock getting it rock hard for round # 2. Kissing my neck and chest, then sucking me relentlessly hungry for more. I jumped off the bed and grabbed another condom from my Khakis and let her do the honor of putting it on once again. casino şirketleri
She said to me in a soft voice. Just let go honey if you have to cum. I’m thinking, shit I want this to last cause I don’t know when I’ll have a chance to do this again.
I told her I want her doggie style on the bed. She assumed the position just Iike a woman suppose to. Perfect, submissive and ready to be pleasured and give pleasure. I positioned myself right behind her and she position perfectly in front of me. She grabbed the lube and did what she’d done before. I was so hard and eager to fill her love hole once again. I grabbed my Cock and proceeded to tease the opening of her hole. I push my Cock inside of her. It felt as though she had gotten tighter from the first time. OMG ! What a feeling and experience I would never forget.
I stroke her pussyhole for what seemed like forever, I was having an experience of a lifetime. An experience with a beautiful transwoman a Milf transwoman at that. I would cum not once but twice while stroking her pussyhole. Why ? Because when said, I’m cumming Baby. She tightened up around my Cock while I was cumming, thrusting her hole and shot another load right after. Wow ! Fucking ! WOW. WHAT AN Amazing experience. I laid on top of her while she milked my Cock dry with her pussyhole. When I pulled my Cock out of her I was still throbbing. I laid on my back and she began sucking and licking my Cock again. My right leg would not stop shaking. It felt so fucking good. I was truly in Lust with this woman.

We cuddled for a while in bed then she gave me a wash cloth and I got cleaned up. She asked me if I would be back and did I like it. I grabbed her and pulled her close and planted my first kiss upon her lips. She stuck her tongue in my mouth and I returned the same. We hugged and she escorted me to the front door of her apartment. I turned around to get one last look of her before I hit the road and smiled at her and she blew me a kiss. I walked to my vehicle happy, satisfied and mesmerized by my experience.

After arriving at home around 3am I settled in bed and masturbating on the night I had with Lilith.

I would see her on and off for several months in between for about a year. Shes now in a relationship and I don’t keep in touch. But the memory of her and the eroticism we share is well kept in my brain.

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