tagTransgender & CrossdressersLong Time Friends First Time Lovers

Long Time Friends First Time Lovers


I had always had difficulty connecting with anyone or attracting women. Being 6' 5" tall and 140 lbs when I was 18 during my senior year of high school, my appeal to women wasn't very high. I was never the wrestler or jock material. Being from a small town in South Dakota if you weren't athletic you wouldn't get the ladies. So being the loaner I was I had already developed a liking to women's clothes. I had developed quite a collection that I would often wear bras, panties, and pantyhose, or thigh highs under my school clothes. I loved the way they felt against my smooth shaved skin. There were many times at school when I thought I would get found out, and am rather sure I would get my ass kicked badly if anyone did find out. But family being family I couldn't keep a secret hidden for long, considering my collection took up almost my entire bottom dresser drawer.

Being that I didn't have anyone in my life to go out with romantically. I spent a lot of my time with my best friend, Doug. We would go to movies, hang out playing playstation, or go to the bar and shoot some pool. Many times we spent almost all night at his house. But being Doug always talked softly around my dad. My father would say Doug was gay all the time to me, so they didn't get along very much.

One day Doug told me that his mom and his big sister were going to be gone for the weekend. They were going to some big flea market with his grandmother and aunt. He asked if I would like to come over and stay the night. I jumped at the chance to get out of my house. So I packed up some overnight clothes, and some sexy stockings and bra and panties with a nice black slip, and a pair of ankle strapped pumps. I didn't know if I was going to wear them but I so had the urge to get dressed up.

So after school I went to Doug's house. Were we watched movies played games, and even got drunk a little bit. But it was getting late so we got dressed for bed. I went to the bathroom and looked at my collection I brought with me. I chose to wear the charcoal bra and panties and the barely there thigh high stockings I had. Thinking they wouldn't be seen with a pair of socks and the stocking tops under my boxers and a t-shirt over the bra. Being more than a little tipsy I didn't care if someone did see.

So I went back to the bedroom, and crawled into the sleeping bag. Doug was setting up another movie to watch, and got a couple more drinks in us, before I passed out. I woke up the next morning with a warm comfortable feeling, and realized that my best friend had crawled out to of his bed and into my sleeping bag. Opening my eyes I saw my boxers, socks, and shirt lying on the floor in front of my pillow. I wanted to just die, I was just in my bra and panties and thigh highs. And wrapped around me was my best friend. So after about 30 min or so I just thought what the hell. Closing my eyes, I tried to fall back asleep. I felt my friend change positions I then knew why he was so uncomfortable. Doug had a raging boner pressed up against my panty covered ass. It felt wonderful; I slowly got up the nerve to slide my hand down around his tool and started to stroke him. He seemed to enjoy what I was doing to him, he would lightly trust against my hand and ass. Wakening to the pleasure of my hand around his tool, Doug asked me, "Why are you dressed like this?"

"I love to dress up," I replied, "Why are you in bed with me?"

Laughingly he said "I was drunk, but when I got up during the night. I saw that you had wrapped the sleeping bag between your legs and saw your boxers rode up and were showing your thigh highs, I just had to touch you."

Just taking advantage of a good drunk friend then?

Doug said, "Like your really complaining with your hand stroking me little missy."

Doug, I have never had been with anyone, but have thought about it a bunch of times. I mean I wear women's things because I like it. I would like to try to be in a relationship as a woman just to give it a try. I just didn't know who to ask or could trust with this.

Well little missy if you like this so far just relax and I will take care of you.

Doug I would like to go and get ready if that is ok?

Go if you want, just make sure your wearing these sexy panties and stockings.

I went to my bag and went to the bathroom and got ready, pulling out a nice black tight slip dress, and my sexy ankle strapped black 4" high heels that cost me 100 bucks. I walked out of the bathroom with my heels clicking so sexily against the hard floor. I come back to where we were to find that he had crawled into his bed and stripped everything off except a light thin silk sheet. This was nicely tented over his tool.

Wow sexy little missy you look so hot in that,

Well Doug, my dear it looks like you could use some help with that and I crawled up onto the bed and he pulled me down into a loving deep passionate hot kiss, he tried to French me but I was taken off guard by how direct he was. But when his left hand slid up my back and the right down my thigh it made me moan and part my lips and he wasted no time pushing his thick tongue into me

It didn't take long for our kisses to become almost hungry with passion and lust.

I felt Doug's hands on my shoulders with a little pressure I knew what he wanted but he wasn't going to force me to do it. But being so horny I wrapped my hand around Doug's cock and started to lick the now purple head of his thick 9in cock.

Performing light kisses and tongue work on him I got him so worked up he grabbed my hair and pulled my mouth over his cock. Forcing it down my throat, holding me there a second. Just long enough, I started to panic. He let me up to take a breath, and then right down to the base again. He worked me into a rhythm and then he let go of my hair and I was bobbin and sucking for the life of me. I was looking up at his face and watched his eyes glaze over as he lost focus.

God baby your one hell of a cocksucker.

I sucked him for some time licking his shaft and balls. Until he told me to stop and pulled me on top of him and kissed me deeply and rolled us over and spread my legs. He started kissing down my neck and body. Slowly peeling my black slip down, he locked his mouth on my tits. Licking, sucking, and pinching them between his teeth. Slowly he moved down my body to my waist. He let up and slid down to my high heels kissing my ankles and slowly working his way up my stocking covered legs. Slowly rubbing my legs wider apart, till he was just inches from my now throbbing man clitty still encased in my panties. He reached in pulling them aside and exposed my hard clit, which he took into his mouth rolling it around with his tongue. He spent the next 30 min bringing me to the peak of pleasure but never letting me cum. When I couldn't take it anymore, He pulled away and told me to roll over and get on all fours. I did pouting a little, wanting him to finish what he was previously doing.

Its ok baby you will cum here soon but I want that man pussy you have for me. And as he said that I felt my panties slide down my thighs.

I nervously said, Doug I have never done this before.

Doug didn't respond instead his expert tongue licking my now wanting love hole. With the new feelings he brought up I never spoke again.

He licked me until I was soaked and he got up saying, don't move honey.

Yes baby I replied closing my eyes just listening to him open his dresser and rummage around and then a pop and the sound of lube being squeezed from the tube. The sudden shock of cold as it was rubbed into my love hole. The bed shifted as he positioned himself with his rock hard tool pointing strait at me. Knowing that the head I was just sucking and licking will soon is plunging into my pulsing virgin hole.

Now just relax baby, this will be the best thing you have felt or will ever feel.

With that Doug pushed his engorged head into me. Feeling a little pain I instinctively pulled away. But he anticipated this and wrapped his hand on my hips and moved with me and sunk in a little deeper, making me cry out a little. He held me there for a min or so and then worked his thick cock in deeper. Soon I started to feel full warmth of his cock buried to the hilt inside me. When he with drew just to the tip I felt sad and empty, but without delay he slammed back to the base. It didn't take long for Doug to start building a steady pace. And with every thrust my body wanted more and more. Soon I was thrusting myself back onto his tool.

You have such a nice tight ass baby girl.

Shut up and fuck that big cock into me you prick, I replied

This just increased his pace even more. I knew what was coming; I called out Fuck me Doug Fuck my ass. I want to feel that hot cum inside me. I want you to fuckin use me like your bitch. He grabbed my neck with one hand, slamming his monster into me. I felt my own pleasure building along with his. I just lost myself into the wild passion of him just plowing into me.

Good God Corey!" was all he said, then he buried himself to the hilt inside me and I felt a thick torrent of hot cum burning its way into me. With the feeling of his cum filling me, I also started to cum too without touching myself. This also had the effect of tightening my love hole and milking his cock of all that hot cum. Jet after jet of my own hot cum landed between my spread legs and on my thighs and stockings. Seeing this I took my hand and scooped up all that I could. Never before having had the urge to taste cum, I licked it off my hand, every last drop.

With the last thrust into me, Doug and I both laid down with his tool still pulsing inside me.

"Corey honey would now be a bad time to ask you out on a date?" he said with a small chuckle.

I would love to Doug, but only if you buy me dinner.

Love to buy you dinner, but only if you wear something sexy again.

I said playfully, "Ok Doug, but only if you promise to fuck me good afterwards!"

I can't honey. I don't just want to fuck you; I want to make love with you. With that he wrapped his arms around me.

I loved you for a long time now Corey.

And then we both fell asleep.

I knew from that moment on I was his girl anytime he wanted me.

Report Story

bywolfinnights© 4 comments/ 61764 views/ 14 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartRjdelta14, Lucy2999 and 12 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (4 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (4)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: