Out On the Prowl

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Terri gets a date and takes him home.
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This is my fourth story now, and they bring back such great memories. My stories are true to life and I wouldn’t change the events that led to them one bit. The only thing I would do differently if todays advances in medicine were available then is I would have gone through a transition from male to female. Of course then many great things in my life never would have happened.

*****

My ship was getting ready for a WESTPAC, aka western pacific deployment. So it was time to pack up most of my things and put them in storage, but not before some last minute fun before I had to move out of my apartment.

Lots of things had happened just in the couple of short months since I was discovered by some shipmates as a cock craving crossdresser. Liz, my friend and feminization teacher had introduced me to a friend that she said had seen a picture of me and wanted to meet me. Problem was she didn't know I was a bi CD. We met and really hit it off so much so that the only time I wore any fem stuff was when she was back home and not in San Diego which wasn't all that much. But when she was I took full advantage of the opportunity.

It was a beautiful night, warm with a light breeze so I decided on a black mid thigh pleated skirt with a white silk blouse that was very sheer. Underneath my skirt I put on some of the laciest lingerie I had. Black garter with a three inch lace top stockings, and some silk lace panties that made me want to cum just wearing them. Under my blouse I wore a sexy little camisole to cover my c cup breast forms. I went with and auburn shoulder length wig. I wore some low heals knowing I'd be doing some walking. My makeup and jewelry made the package complete. The look was sexy but not slutty, and that's just what I wanted for my night out.

I walked out my door and my neighbor Eric who had by now cum in my mouth and ass several times when his girl friend left him hanging commented how nice I looked and asked if I had a date. I said no, not yet. His reply was well I'm here if you need one.

It was good to know because you never know what will happen once you head out.

It was still early only around 6 or 7 so I went to the Gas Lamp district for a drink. There were quite a few people out and about on this warm night and many of them military guys which I had had my fill of literally.

I found a little club that had a live band playing some soft Jazz, I went in and found a small table and sat down. The lights were dim which always works to a crossdressers favor. The waitress came over and took my order. I took out a book that I had in my purse and started reading it while sipping my drink and I noticed an attractive guy looking at me. I tried not to let him see I noticed him as I peeked over the top of my book. He had light brown hair, a neatly trimmed beard, and was dressed very stylish. I felt a twitch between my legs as thoughts of taking him home with me went through my head.

As I finished my drink and was about to get up and leave the waitress brought me second drink. It was a gift from the guy that was checking me out. I accepted it and acknowledged his generosity with a wave and smile. He took that as an invite to come over and sit with me which I was glade he did.

He introduced himself as Glenn and I said I was Terri then the small talk began. We talked and had a few more drinks, the whole time I wanted to just crawl under the table and suck his cock. Before I knew it was 10:00. I told Glenn that I didn't want to be out too late and he asked if I lived near by to which I said I did. I asked if he wanted to follow me back to my place and maybe we could continue our conversation and have another drink there.

We walked to my door, I saw Eric look through the window giving me a wink as we walked by. We went in and I kicked off my shoes and Glenn sat down as I got us some drinks. He noticed all the boxes and asked if I was moving in or out to which I said out. As we sat there having our drinks I casually hiked my skirt up exposing me garter straps and stocking tops. He saw that and wasted now time coping a feel working under my skirt.

We finished our drinks and Glenn moved closer leaning in for a kiss. It was a wonderful long full open mouthed kiss that lasted a long time as he continued to rub by upper thigh.

I had to slow him down so I pulled back, reached down and undid his pants. I reached in and pulled out a rock hard uncut cock. It was about six or seven inches, smooth and average thickness. I began to stroke it as we kissed then slowly went down and began to lick the head as I pulled the foreskin back exposing it to my anxious tongue. He put his hand on the back of my head as I slowly sucked him in all the way. I came up and told him I needed to change my clothes and I'd be right back.

I came back out wearing a pretty little red night gown with black lace and a matching robe. I kept my panties stockings and garter on more for me than him. I spun around to words of appreciation from Glenn. I walked back over to him and dropped to my knees between his legs and began to make love to his cock with my mouth, licking and sucking him for a good ten minutes or more. He asked me to stand up and I did as he asked. He reached up and slid my panties down. I thought for sure he'd seen my hard on but the layers hid it.

I told him I wanted him to take my ass and a big smile came across his face. I turned around lowering myself onto his rigid cock, guiding it into my ass. I slid up and down on it taking it all in and squeezing as I rose up. Glenn was rubbing my shoulders and back as a fucked his cock with my ass. Our moans go louder and heavier as we carried on. Then in the passion of the moment he reached around looking for my pussy, before I could stop him he found my cock standing straight up. He pulled his hand away and gripped me tightly saying what the fuck is that.

I pulled away and stood up. I lifted my nightgown showing him my hard cock. I thought he was going loose it, but instead he took a drink from his glass looked at me shook his head and said fuck it we've gone this far.

He pulled me back on top of him only this time face to face and I took his cock back in me riding with more passion now as I looked in his eyes. We kissed as he made love to my ass. I leaned back and closed my eyes riding his cock and the I felt his hand wrap around my cock trough the nightie and he began sliding the silky fabric up and down on my hard cock. I could feel his cock get harder and could tell he was about to cum deep in me. He let out some loud grunts and yelled that he was coming. I felt the warm flow of his cum as he buried his cock as deep in me as he could. He continued stroking my cock and when a I got close I lifted my nightie up over my cock so he could watch it shoot all over the two of us. When I came it shot a good foot in the air landing on my thighs and his stomach. I kept squeezing his cock with my ass grinding on it as it went limp and then slumped into his chest.

We stayed there like that for several minutes then I got up and mover over beside him. I asked him if he was mad and he said who the hell could be mad after a fuck like that and kissed me. He put his arm around me has and leaned against him staring at his beautiful cock glistening with our combined juices all over it. I asked if would spend the nigh in bed with me and he said yes.

We washed and went to bed and I fell asleep with him against me in my nightie. I was having a dream that I was enjoying the wonderful feel of getting my ass fucked then I felt a hand on my hips and I awoke to Glenn pumping my ass full of his hard cock. It wasn't a dream, he was really making love to me and told me how good I felt on his cock. He came quickly this time and we fell back asleep with his cock still in me. As we did he reached around and gently stroked my cock until I came again in my nightgown this time.

I woke up early and he was still there sleeping next to me. I got up and did my makeup real quick then slipped back in bed. I went under the covers and took his limp cock in my mouth. I love to feel a cock get hard in my mouth. I sucked until he was good and hard and as soon as he opened his eyes I got on top of him and rode that hard on for all it was worth. Glenn told me to get on my back so he could look at me while we made love. I rolled over spread my legs and he got into position entered me and fucked me real slow. This time before he came he asked If I wanted it in my mouth, I smiled then opened wide for him. I took every drop and swallowed it down, it tasted so good I had to clean it all off for him.

We took showers and got ready for breakfast. I got dressed in a blue silk dress Glenn in the clothes he had on the night before. We ate breakfast and talked some. Glenn got up and ready to go but before he did he said that the dress I ad on was just making him horny as hell. Glenn stood me up, turned me around, lifted my dress, pulled my panties to the side and just took me right there over the kitchen sink in front of the window. I loved every minute of it.

I could see Eric watching with a wicked grin on his face. I winked at him and smiled.

Glenn finished up pulled up his pants gave me a last kiss and left. I watched him go down to his car and drive away from the balcony.

Before I knew Eric was standing there beside me. He asked how my night was. I hugged him and said my night was fantastic but my morning has been unfulfilled. Eric looked at me and said I saw you getting fucked through the window.

I know I said, I took his hand and put it on my hard cock straining behind my panties and said but look what he left me with.

I brought Eric into my apartment dropped to my knees got him hard in my mouth and let him fuck me for as long as he wanted and as many times as he wanted as long as he sucked my cock in return.

It was a wonderful morning after all.

I never saw Glenn again after that night, and I only had two more weeks until I had to move back to the ship.

Eric would throw me a party I would never forget before I left though, and I cant wait to tell you all about it.

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AnonymousAnonymousabout 9 years ago
SaraCD

Love it Love it I only dream of doing something like that!

thongpantythongpantyabout 9 years ago

Love your stories, more Please!

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