I know you were quite taken back at my sexual event of weeks ago, yet you didn’t seen that upset which made me more concerned. So I figured I write you and let you read the way my feeling were going, the funny part is that they went the same way as they do for you besides being sexual I have ever daring love for you. We have been so truthful in our relationship and you have accepted Karen
Well you know Karen my girlfriend, well we made reservations at the Nassau House for a long weekend in Key West I think it was in August of 2001, but at the last minute Karen had a emergency and had to fly to San Francisco. So I said hell I’m going anyway I need a vacation badly. Like most of the bed and breakfast there its run my gay guys, but really nice guys and don’t talk funny either. The Nassau House is really nice big old house with a small topical pool in the back and its only two blocks from Duval Street, the main drag in Key West. I got there in the late afternoon after checking in I walk down to Duval and browse through various shops and stop in at few really neat outdoor bars for a drink. I figured let me get some dinner cause I wanted to go to Earnest Hemingway’s old hang out at Sloppy Joes and see their show and listen to some soft jazz music.(Sex Stories)
As I walk in after dinner I’d figured I’d just sit at the bar being I’m alone. I see and empty sit, which was perfect to see every thing and everyone, cause the people here are really worth watching cause their all wild an some also weird, in a nice way.
So I sit my ass down next to this couple and order a black Russian, nice after dinner drink. Within a short time I am talking to this women and find out she is alone as well, she is very, very pretty mature women in a sexy full dress with tits that are full and cleavage ever so nicely I look and look.
She introduced her self as Sandy from then on we start talking a mile a minute to each other and I was so intrigued with her long black hair and her stunning pretty looks and those breast that were so soft looking I just want to touch and kiss then. When she told me she was 36 I nearly fell off the stool cause she look so much younger. Sandy said she was from San Francisco and came over to Miami to see her s****r and was going to come down here with but her s****rs plans fell through. Then I told Sandy about Karen my girlfriend who was suppose to be with me and that we had made reservations to go out on the 40 foot catamaran to go diving out on the coral reef. She gives me a big wonderful smile said “can I fill-in in her place with you, I’ll make up the dollar difference please”. Without a hesitation I said yes. With that she gave me big hug and kiss which made me squirm down below, I don’t know what happen or why I just turn to her and kiss her firmly on the lips. I wanted to slip her a little tongue but she beat me to it and for a split second we were tonguing each other, now I was wet I remember that for sure. We broke apart quickly and I noticed the gal barmaid was just smiling at us, and asked if we wanted another drink, both getting a little happy from the drinks and we said sure. I asked Sandy if she like to walk over to the Hogs Breath bar for a while I said its less noisy and has nice outside tables for a little privacy and I’ll give you all the information on the dive trip tomorrow. (Adult Stories)
We sat down in a area away from the bar, Sandy walk up to the bar to get our drinks when she came back she sat real close to me gawd I could feel the warmth of her body, now my wet pussy is really tingling. We talk some more about sexual things we both like and then all of a sudden we were kissing again long hard and very wet, I felt her hand under my skirt and rubbing my inner thigh. My hand went to her breast and slid in to her dress to rub a perfect set of tits. After a few very heated moments Sandy broke apart and said Cindy I have to tell and show you something, I am a little bit different than other women. I look at her and babbled something and it came out, so what, so show me, what is it and finally Ok. Sandy took my hand and placed under her skirt and into her crotch; there I felt a cock with a hardon. I have no idea where my head was I look at her smiled and said its wow and kiss her madly and start playing and rubbing with her cock, I couldn’t believe what I was doing but for some reason I didn’t care cause I loved the site of this gorgeous women and the feel of a hardon I was just so sexually aroused.
We broke apart before we went down on each other; I told her I didn’t mind that she was a transsexual and that I still like her, as she was a good and wonderful friend. There were a thousand questions I had; we talk it all out and now and then rubbing each other wherever we could, wet long kisses and so forth.
Basically Sandy in her early teens as a boy just didn’t feel right as a boy, voice never changed even develop boyish breast and a very slim sort of figure. She said she went through hell between 13 and 21 but at 20 on her own was making good money and saving every dime so that she could go through the changes from man to women.
She moved to San Francisco and changed her appearance as a women but still a mans body, she laugh and said I was a very pretty man even went on dates very careful to have no sex. Laughing she said I still like women better, I guess I’m a mix up lesbian. Finally she went thought all the changes from tits, ass and all hair removal while still maintaining here job in Frisco.
Sandy said it cost her a fortune but it was all worth it in the end and now I’m really happy women, and that her sexual preference was women. I held her to me and we kiss very passionately and told her I’m glad.
I ask Sandy if she like to stay with me tonight because we have to be at the dock early in the morning, plus it’s a queen size bed big enough for us both. With a wet lick of her tongue around her lips and said yes, but I have to pick up some thing at my place for tonight and tomorrow.
When we got back to my place I asked Sandy if she like to go for a swim in the pool out back. We both got our suits out and started to undressing as I was standing there naked looking at Sandy she turned towards me also very naked and gave me a very sexy pose and asked me if I like what I saw, my response was your so perfectly beautiful as I walk over to her and rap my arms around her and gave a very sexy wet kiss. I could feel her beautiful breast against mine as we really kiss ever so dirty then her hand went to my breast and played so heavenly. All of a sudden I could feel her cock growing against my pussy at that I became a wet mess. So there we were in a total sexual embrace, she playing my pussy and I’m stroking her cock. As we fell on to the bed I roll on top of her and start kissing her entire body, sucking her tits and down to her belly. I knew what I wanted and as I held her cock in my hands my tongue licking her cock. Sandy swung my legs over her and I could feel her tongue probing my clit and then sucking my inner pussy. My mouth went down on to her cock like a pussy in heat, up and down and all around. I knew with a second I was going to have one of my massive orgasms, I ejaculate some times, I could also feel her cock was throbbing and was going to cumm any second. Ooooohhhhh my gawd I knew I was cumming into Sandy mouth but I was so intent on having her cock cumm that when she did cumm in my mouth it was so intense I had to lift my mouth off of her cock and just let her cock cumm more as I could only swallow some. I swung around and fell on to Sandy kissing and licking cumm off of her face.
Funny she said I’ve never seen a pussy cumm like your does, gosh that was so beautiful. We laid their for a while in each other arms kissing, but as I kept stroking this still hard cock Sandy rolled over on top of me and I guided her cock into my pussy. Oh how good that felt my legs went around her waist and my mouth sucking on her tits like I wanted her milk. I could feel the orgasm building again as she pounded my pussy furiously then I could feel Sandy cumming in me as she was sucking my tits with passion, with this I just went into a second orgasm too.
We laid their total dripping in sweat and my pussy total fill with our cumm; when Sandy rolled me on top of her and was still kissing me and my tits like so softly and playing with my cumm filled pussy. (This drove me over the edge; I have only done this to myself when masturbating) Sandy work the cumm from my pussy and played it into my asshole and then probe my asshole with her fingers going in and out, I grab her cock and just start jerking it as fast as could. I remember screaming don’t stop, Sandy was kissing me sucking my tits, my nipples felt like they were going burst. Sandy asks me if she wanted her to fuck my ass, in rage of hot passion I just said yes do it please. I got the KY jell and Sandy lube in an around my entire asshole and her cock, I got on all fours as Sandy eased her cock into me, it felt a lot bigger than my small dildo I used.
As Sandy eased into me I push back on her cock hard and she was all the way up my ass. My ass was no longer a virgin as Sandy fuck my ass for as long as she could cause neither of us had any strength left as she pull out and fell down next to me.
I kiss her and lick her tits and told her I like it a lot really. With that we just fell asl**p in each other arms till morning.
As morning came we shower and wash each other all over and when down to have breakfast on the porch. The guys had put out all kind of fruit, buns and coffee it was just perfect as we both smiled at each other. We finish and went to the room to put our suits on both of us in a bikini, I look at Sandy and said were the fuck did you put your cock up your asshole. She smiled and said it a special kind of suit, but don’t make me get a hardon Cindy.
With that we drove over to the dock with our gear and had a wonderful full day out on the water.
We stayed together for the next three days doing every thing there is to do in Key West, bar hopping dinners back to bar hoping, even found an all girl bar, which was kind of interesting in another way. We even took a moon light sail on that same big catamaran, it holds about 30 or so people. Of course we continue to have sex in every way possible every night and morning, we did buy a double-ended dildo in a adult store that we used in various ways. I’ll leave that to your imagination, which is probably correct. I have to admit I never had so much wonderful sex in a four day period and I know I have never been loved that much either.
I know you want to ask so what happened???? We both decided in our best interest was to just part and go our separate ways, she did have a girlfriend back in Frisco and that sexual time we had was the best she had ever had also.