tagTranssexuals & CrossdressersCrossdressing For My Boyfriend

Crossdressing For My Boyfriend


My name is Chris and I'm a 25 year old, white, bisexual male. I stand 5'9" and weigh 135 pounds with light brown hair and brown eyes. I've always had somewhat of a feminine body and I've always enjoyed being a "bottom" when with other men.

I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of me. Mark is 27 years old, 6'2" and weighs 195 lbs with brown hair and a very hot body. He works out a lot and plays some sports. You could say he's a very sexy jock with a very large cock!

After we met, we quickly became fuck-buddies and we loved every minute of it. I immediately became familiar with Mark's massive cock, which measures over 9 inches. It felt so good in my tight little ass. I knew right away this was the cock I had been craving all my life! We fucked constantly and ended up moving in together. I promised Mark I'd do whatever it takes to keep him satisfied. I loved giving him blowjobs and I loved the taste of his hot cum. Our favorite position became doggy-style, because Mark is able to slide his huge cock so deep inside of me and it always makes me feel like such a little slut. And of course I love being Mark's little slut!

Right after I moved in with Mark, he had a birthday approaching. Two weeks before his birthday, I asked him if he had any wild fantasies that I could fulfill. I was willing to do anything that he wanted. Mark was a little shy at first, but after a few drinks, he told me that he's always fantasized about me dressing in women's lingerie for him! I was somewhat surprised, but SO TURNED ON!

I immediately began stroking his enormous bulge and whispered to him, "That can be arranged."

I had always been a bottom and I have a very feminine body, so I knew I could pull it off. And the thought of me dressing in sexy lingerie for my boyfriend's birthday made me so horny! I could not wait to do it! The very next day I called my 22 year old sister Shannon at college and asked her for advice for picking out lingerie. She has always been so supportive of me and she didn't mind helping at all. Shannon was a little jealous that I had such a hot boyfriend that loved to fuck me all the time; but she agreed to help anyway.

The very next day, Shannon and I went shopping at Victoria's Secret and Frederick's of Hollywood. I bought several different lingerie outfits with Shannon's help and I could not wait to get home and try them on. I wanted to keep it a surprise, so I made sure Mark was at work when I was trying on my lingerie.

I purchased a wide variety of lingerie outfits, including a black lace bustier with fishnet stockings, a pink lace babydoll, a red bra and garter belt set, and a very sexy white lace corset. After trying on all my new outfits, I finally chose the white lace corset to wear for Mark's special birthday night. The corset also came with a matching thong and Shannon helped me pick out sexy white thigh-high stockings to go with the outfit. She asked why I chose the white lingerie. I explained that since this was my first time crossdressing, I wanted to look like a sexy little "virgin" in all white.

Shannon looked at me and said, "Trust me Chris; you won't be much of a virgin after Mark sees you in that sexy little outfit."

A few days later, it was finally Mark's birthday; the day we had been waiting for. He had to work until 6pm, so while he was at work, I got ready for him. I shaved my body so that I was totally smooth for him. I put on some perfume that Shannon recommended and then it was time to slip into my new lingerie. I slipped into my white corset and put on my dainty little thong. Then I slowly put on my white thigh-high stockings. I NEVER FELT SO SEXY! I lit a few candles just before Mark got home, and when I heard him approaching the front door to the apartment, I met him there wearing only my lingerie! His mouth dropped as he could not believe how fucking hot I looked!

I immediately went down on him before he could even close the door. His cock was throbbing hard and jumping with excitement. I pulled his pants down and began deep-throating his juicy 9-inch shaft.

I looked up at him and whispered in a very feminine voice, "My virgin pussy has been waiting for your big cock all day. I'm going to be your slut tonight."

It didn't take long until his hot, tasty cum shot deep into my mouth! Mark couldn't control it; he was so turned on. His cum tasted so fucking good! It was such a huge load of warm sperm, and I began to swallow it.

I kept some of Mark's tasty juices in my mouth and motioned for him to go into the bedroom. I knew I needed to get his dick hard again and I knew exactly how to do it. Mark took off the rest of his clothes and he sprawled on the bed. I jumped up on the bed and pulled both his legs up in the air. Then, with Mark's hot cum still in my mouth, I began licking his tight little asshole. I began to transfer some of Mark's warm jizz from my mouth into his supple man-hole. And he loved every minute of it! In no time, his massive cock became erect again as he watched me licking his ass while dressed in my sexy white lace lingerie. His huge balls started to swell as they began filling up with more cum. And this time I knew his cum was destined for my "pussy"!

Then it was time for Mark to fuck his little "virgin" dressed all in white. I quickly got on all fours with my awaiting ass in front of him. I smelled like Victoria's Secret perfume and cum. What a combination!

I whispered to him, "Happy Birthday baby! This pussy is ALL yours!"

Mark quickly slid my thong to the side and began eating out my "pussy". He got it nice and wet and after a few minutes, it was ready to take his giant 9 inch cock. He slid his long, hard shaft into my hole very slowly at first as he held me by the hips. With his stiff cock sliding deeper into my ass, he began to caress my body. Soon his cock was buried balls-deep in my tight hole! I could feel his huge mushroom head poking deeper and deeper inside of me. I felt Mark's cum-filled balls rubbing up against the entrance to my hole. His stiff cock was throbbing with joy deep inside of me and my entire body began to shake in ecstasy.

He examined my body and said, "Thank you baby. You look SO FUCKING HOT! This is by far the best birthday present ever!"

As he began to thrust his throbbing shaft in and out of my "pussy", I moaned and screamed like the little slut that I was. Needless to say, it didn't take long for Mark to shoot another huge, sizzling load of cum. This time though, his sperm shot deep into my awaiting ass. It was the hardest he ever came and it felt so good as his dick erupted inside of me! Shortly after, he collapsed on the bed with a smile on his face. I smiled back at him as I felt his warm jizz dripping down the inside of my legs and over my thigh-highs. I began stroking my cock and immediatley shot a huge load of my own sperm onto Mark's chest as I moaned in ecstasy! It was by far the BEST FUCK EVER!

I called my sister Shannon up the next morning to let her know how it went.

"How did he like the white outfit?" she asked.

I simply replied, "Let's just say I'm not much of a virgin right now!"

Report Story

bydmk241© 13 comments/ 145558 views/ 36 favorites

Share the love

Similar stories

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

heartlexiwhitman28, pi77 and 34 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Riki1942r06/19/17

I Know

I know just how hot it is. I have cross dressed for several of my Boyfriends in the past and, with a couple of them, it became the normal thing. Like Chris in your story, I had dressed in private formore...

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

Show more comments or
Read All 13 User Comments  or
Click here to leave your own comment on this submission!

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):

You 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: