First Shemale

Lately I've been thinking about sleeping with a shemale. I'm in my late 60's, look 10 year's younger and, for some reason, I'm really attracted to shemales. There are a two LGBTQ bars in my area and I found one that I thought might work. I had no idea what I would do once I got in the bar, but this was an itch that I had to scratch so I went for it. When I pulled up to the bar the parking lot was was packed so I parked my Porsche way in the back. As I started walking to the front door, I immediately realized I was not properly dressed for the evening, somehow my khaki trousers and polo shirt were going to stick out...and not in a good way. Oh well, too late now. I had to wait in line and finally got into the bar about 9pm, it took me 30 seconds to realize this wasn't for me. The music was so loud I couldn't think straight and it looked like a giant mosh pit of dancing and flesh, so I had a quick Diet Coke and headed for the door. As I was leaving, I almost knocked over a beautiful, petite shemale who was just arriving with her friends. She smiled and asked why I was leaving so early. I told her that this place wasn't for me and that I was going to grab a quick burger and head home. With that she grabbed my arm, turned to her friends and said she's going for a burger with me. And off we went.

We got into my Porsche and drove to a burger place that's close by. Sara, my new friend was 25 years old and had been transforming for the past 7 years. She was a pre-op who has been taking regular hormone injections which really enhanced her feminine features. She lives alone having just broken up with her boyfriend. She asked about me and I told her I was a widower and also live alone. She told me she was looking for a Daddy to take care of her sexual, financial, and emotional needs.. In exchange, she would serve her Daddy as he pleased and he'd never want for anything. I nodded and told her I'm sure she'll find the right guy. I told her I know what she is looking for, but I'm not sure I'm the right man for her because of our age difference.

When we walked into the restaurant every eye was on us. She was beautiful, very passable, and over 40 years younger than me. She was wearing green leather pants, with brown boots and a white bustier. We sat down, ordered quickly, started chatting, and had a great time. She was a lot of fun and loved to laugh. I couldn't believe how comfortable I felt with her and being touched by her. At one point I looked at her crotch and there was an enormous bulge, I so wanted to caress it, but resisted my urge. I suggested we leave and got up and walked to my car. I opened her door and asked where she lived so I could drive her home. She told me she didn't want to go home, she wanted to go with me and show me how she would take care of me.

Against my better judgement I said sure. Sara smiled and snuggled next to me. When we pulled into my garage she leaned in and kissed me, at first very gently and then a full on french kiss. I was really getting aroused and told her so. We got out of the car and went inside. I asked if she wanted anything to drink and she said she'd have a white wine. I went into the kitchen to get it and by the time I got back she had already taken her pants off. She was standing in her bustier, boots, and silk panties with her semi erect 5" cock protruding out one side.

I gave her the wine and she drank it in two gulps. She started kissing me and grinding her cock into me. I picked her up and carried her to my bedroom. By the time we got there she was writhing in a pre-orgasm state. She asked if I would suck her cock and I said yes. I had never sucked cock before, but I wanted to suck hers. I gently kissed the head with my lips and swirled my tongue along the ridge. She told me to deep throat her because she was close. I opened up and took the whole cock in my mouth. She wasn't long enough to trigger a gag reflex so I deep throated her while she writhed with pleasure. After a few minutes her breathing got shallow and I knew she was close. Her cock started twitching and I could feel her squirt. It wasn't a lot, but it was warm and sweet and I savored every drop. I swallowed most of it but when she was finished I continued sucking and got a pretty good amount that I kept in my mouth. After cleaning her up I brought my lips to hers, opened my mouth, and shared her load by french kissing her.

We snuggled for a bit before we fell asleep. I hadn't cum yet, but I was spent from giving my first blowjob. I woke up the next morning with Sara kissing me all over my face and neck and gently stroking my cock. I was getting incredibly turned on and my cock was ready to explode. Sara told me she wanted me inside her. I told her I didn't have any condoms, but I could go to CVS once they open. She told me she had lube and condoms, but she wanted it bareback because she wanted me to make her mine. She laid on her back, spread he legs, and beckoned me to cum inside and breed her. Her cock was getting hard as I lubed up her hole and pushed the head of my engorged cock in her ass. I don't know if it was the angle, or the lube, or my cock's stiffness, but it went right in. She was writhing in excitement and begging for me to push it deeper, which I did. I put it all the way in and started passionately kissing her and pounding her ass. We were moving in a great rhythm when all of a sudden I felt her cock twitching and she screamed that she was cumming. The sensation of her warm cum between our stomachs was too much for me and I told her I was going to cum. She instinctively clamped down on my cock and I lost it, I pushed my cock all the way in and shot several massive loads into her ass. After cumming I kept my cock inside her as we flipped around and she straddled me. As cock softened and came out, all my cum leaked out of her onto my stomach. Sara laid down on top of me and we fell asleep.

I woke up a few hours later spooned up next to Sara with the smell of cum all over me, her, and the sheets. She looked great and was sleeping very soundly until she felt me stir. She asked if I would take her home and I said I have a better idea. I suggested we get cleaned up, go clothes shopping for her, and then go to lunch.

I hadn't been woman's clothes shopping in 30 years, but I don't remember it ever being this much fun. I took Sara to the Saks and Nieman Marcus stores at the mall and told her to have at it. It was so much fun watching her run around trying to decide what to buy. She finally settled on a bunch of outfits and shoes, but more importantly settled on an outfit to wear for lunch. It was a black leather mini skirt with cream thigh high boots and a pink cashmere sweater. She looked incredible, but before we left the saleswoman whisked her off to hair and makeup for a quick touchup. When she emerged she looked absolutely stunning.

I took her to a restaurant on the outskirts of town and got a table in the back where I knew we'd have privacy. Sara ordered a Cosmo and I got a Diet Coke. Sara couldn't stop talking about how much she cared for me and that no one has ever treated her this well. She guided my hand under her skirt to her semi throbbing cock. I focused on rubbing the head with my thumb while Sara massaged her right tit. She pulled my head close to her and full on french kissed me as she came in my hand. She was still shaking from her orgasm when I closed my hand and pulled it out from under her skirt. She was glowing from her orgasm as she watched me open my hand to display her load. Without hesitation I took my tongue and licked every drop of her cum from my hand and then french kissed her to share the load.

Just then our waitress came by and asked if we know what we'd like to have for lunch. Sara said she'll take another Cosmo and a salad. When the waitress asked if she'd like some protein on her salad, she looked up, stuck out her tongue, and said she just swallowed all the protein she'll need for the day.