Dressing for Larry

Story Info
Mature bi tries crossdressing.
1.3k words
4.51
26.3k
26

Part 1 of the 2 part series

Updated 06/09/2023
Created 07/05/2018
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loneguy01
loneguy01
172 Followers

I met Larry through a gay web site and had a threesome with him and my friend Justin. Justin lived 50 miles away and it wasn't convenient for us to meet very often. Larry, however, lived in my city. He had mentioned that he would like to meet again and it would turn him on to see me in lingerie. I went on-line and saw images of men in lacy panties, silky slips, fishnet stockings and my cock began to grow rigid. I knew I had to buy some items.

I bought a white satiny top that resembled the top of a slip. I found some matching panties and some white stockings. Checking myself out in the mirror, I decided to invest in some make up - just eye liner and lipstick to start. I do not have much body hair and I shaved my chest and legs. I had been shaving my pubic hair for years. A little perfume completed the look.

I made a date to meet Larry at his place at 9:00 PM the next Friday. I was very nervous as I rode the elevator from my condo to the parking garage. I had clothes on over the lingerie, of course, but I was also wearing make up. Fortunately, I did not run into anyone.

I parked in Larry's driveway and took a deep breath. "How would this go?" I thought. The walk to his door took seconds that seemed like hours. Larry answered the door and I entered. We didn't say a word as I discarded my male clothes and stood before him in my lingerie.

Larry smiled and said "kiss me, dearie." We embraced and kissed passionately. I broke off and slid to my knees where I undid his belt and pulled his pants down. Larry's cock is about 6" long but almost as wide as a beer can. My mouth engulfed his fat cock and I began to feast on it. My tongue swirled around his cock head as I fondled his balls. I had to stretch my mouth to accommodate his shaft but I soon managed to take it all down my throat. Larry was obviously enjoying it as he soon began to leak copious amounts of pre-cum. I loved the taste and use my tongue to massage his cock head with it. Suddenly, he grabbed my head and began fucking my mouth. He was totally in control but it did not take long for him to send streams of cum down my throat. I managed to pull back a bit on his cock so I could suck every drop out of him.

"You are a good slut." he said. "I want you to model for me, dearie." I pranced around the living room and wiggled my butt - I had never been a particularly femme type before but my performance gave me such an erotic thrill that I knew I would be from now on.

Larry too me by the hand and led me to the bedroom. He quickly stripped and I admired his strong body - he is built like a linebacker although he is only about 5'-9". He works out with weights and his muscles were impressive.

Larry sat on the bed and ordered me to dance for him. I am not much of a dancer but I did my best imitation of one. He reached over and began to rub my ass through the silky panties I was wearing. "You like this don't you?" he smiled after noticing the large wet spot on the front of the panties.

"I love it, I love being your slut!" Larry pulled my panties down and had me get on the bed. I was on all fours and he began to play with my ass. It felt so good. Then he startled me when his tongue invaded my ass. I was soon moaning with pleasure. I loved it but it only intensified my need to be fucked. I begged him to fuck me. "I am going to fuck you bareback!" I was a little apprehensive but my lust overcame my hesitation.

Larry wanted me on my back so he could fuck me like a girl. He lifted my legs on his shoulders and spread some lube over his cock and then he started to shove his thick man meat into my boy pussy. It was tough going at first but he was able to sink it balls deep before too long. I loved feeling so full, I felt sexy with my stockings and silky top still on with Larry's shaft buried deep inside me.

Slowly, Larry began to fuck me. He pulled his cock back almost completely out of my ass and then plunged it back in. I felt a tingling sensation each time his cock banged my prostate. Larry smiled down at me and told me I was a good little slut and that he was going to breed my sweet ass. I loved being his slut. He kept a slow pace for quite a while and it was driving me crazy. I told him I loved feeling his cock go in and out of my ass. Larry's expression changed and he began to pound my ass. It was driving me wild. I got quite vocal - "Yes, fuck me hard! I need to have your cock pound my ass. I need it so much!" This seemed to excite him even more and he fucked me even harder. Soon I could feel the walls of my ass being flooded with his seed. Larry kept his cock in me for a few minutes after he finished cumming. He pulled it out and my ass was leaking his cum. I felt so sexy. Larry had me stay with my legs spread so he could take a picture of my ass with his cum leaking out.

After that, we rested for a while. Larry put some porn videos on and we lay back watching them and sipping some whiskey. After 2 or 3 short movies, my mouth was drawn to his cock which was still semi-hard. My tongue soon had it at full attention. I gave him a long, slow, sloppy blow job. I would lick his cock like an ice cream cone and then run my tongue all around his cock head. I loved worshipping his thick man meat. He told me he didn't think he could cum again. However, I was able to coax another load out of him. I kept sucking and licking for a few minutes after he came to be sure I didn't miss a drop. It felt so erotic, I stroked my own cock while I did this and I shot a huge load into my hand. I showed it to Larry and then lapped every drop of my own cum too.

We had a few drinks after that and we cooled off by skinny dipping in his pool. I spent the night there and when I woke up the next morning, Larry was lying on top of the covers with his cock lying there looking so appetizing. Naturally, I woke him by sucking his cock. He looked up and smiled at me. "You are such a good slut." This made me happy and I was able to suck another big load from his big cock.

We had some coffee and finally I washed off the make-up, dressed in my male clothes but wearing my lingerie underneath. We said goodbye but Larry told me he had some friends he would like to share me with. That idea really excited me. Then he said, I would have to be completely dressed as a woman. I wasn't quite sure if I could pull that off but it started me thinking. That is for another story, though.

loneguy01
loneguy01
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AnonymousAnonymousabout 1 year ago

Loved it

AnonymousAnonymousover 1 year ago

I totally am not fem nut love to dress fem anyway and I want to get fucked on my back taking my lovers cock deep inside my pussy

Riki1942Riki1942almost 4 years ago
Me Too

Me too! I love to dress up, especially for sex. I like to go the whole way with full makeup, breast forms, dress, pantyhose and heels. My boyfriend always cums up my ass raw and I only go bareback with him.

I know what you mean about being so turned on that you let a guy fuck you bareback. There have been a couple of times in the past, when I wasn't in a relationship, when I couldn't resist.

It always happened when I had been fooling around with the guy for a long time, gotten really horny, hadn't rolled a condom on him yet and we had gotten into a position where his cock was sliding around between my ass cheeks. I learned to put a condom on guys before things got that far along because, once I feel his cock rubbing against my hole, I'm too far gone to resist the need to have his load up my sissy hole.

I can also relate to what you said about how you "managed to pull back a bit on his cock so I could suck every drop out of him." When I suck a guy all the way off, I like to have enough of his cock out of my mouth that I can have my hand around it when he cums. I have never overcome my gag reflex, have never been that good at deepthroating and I prefer to not have him shoot it down my throat anyway. I like to take his whole load in my mouth so I can feel it in me and taste it before I swallow.

Riki

DeborahAnneDeborahAnneover 5 years ago
Dates

Iused to make dates on the ole AOL chat rooms, I would take my dress or skirt and blouse, my bra and inserts, a wig and high heels, as I always wear hose and panties it was so fun to appear and then have sex with the person I had the date with. Sure do miss those chat rooms can not find a man to please any more. da.cd@frontier.com

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