Crossdressing

bikerbear600

First Time With A Crossdresser: Part 1 of 2

Scott looks for something different after his divorce and finds Jenny

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on...Read On

Added: 17 Jun 2015 | Category: Crossdressing | Avg Score: 4.95 | Words: 4,921 | Tags: first time  anal  crossdress  transvestite  bisexual  oral  rimming   | 11 Comments

vanessagrrl

Memoirs of a Crossdresser: Chapter 1

My True Story Chapter 1:  I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should...Read On

Added: 01 Jun 2015 | Category: Crossdressing | Avg Score: 4.33 | Words: 1,627 | Tags: autobiography  crossdressing   | 8 Comments

ThePhantom

Once Again in silk Part 2

As sundown approached on Saturday I showered and got ready to attend the opening of an art gallery that a member of our organization was sponsoring. I selected the suit, shirt and tie and then I retrieved the white silk panties from the laundry room. I wonder if Darlene questioned herself on the fact that I accepted her request without protest? They were beautiful and just running my...Read On

Added: 10 May 2015 | Category: Crossdressing | Avg Score: 5 | Words: 1,368 | Tags: panties  suit  art gallery   | 5 Comments

tvk3983

Erica Loves It (Part 1)

Erica discovers sex

For my entire life, I've always thought it was so unfair that girls gotto wear all the really cool clothes. They were softer material, better color choices, and looked so much better. In fact, when I was very young I wore dresses whenever I got to play with the girl next door, but that was always for the tea parties and such we liked to have. But by the time I discovered sex and masturbation...Read On

Added: 30 Apr 2015 | Category: Crossdressing | Avg Score: 4.93 | Words: 9,139 | Tags: cd  anal  oral  dp   | 6 Comments

ThinkKinkyThoughts

The Bodysuit

A guy tries a new 3D printed female bodysuit technology

“The process is actually very simple Mr. Smith,” she said. “It is very much like 3D printing, just using different materials and in a printer that prints on your body. We can print anything on top of your body to make you look however you want. The technology was originally developed for use in movie special effects, but we have seen there are, well, more personal uses that some of our...Read On

Added: 14 Apr 2015 | Category: Crossdressing | Avg Score: 4.73 | Words: 7,177 | Tags: crossdressing  bodysuit  strap on  nails  hair  makeup  girlfriend   | 6 Comments

thatfemininUrge

A New Chapter

Sensual Bliss

A few things have changed. One, I have accepted my desire and need to fulfill that urge to become feminine and girly. Two, having accepted that, I also had to invest to make myself look, and become as girly as I could. That led me on a near year pursuit to create a better feminine appearance than just using two suntan body stocking to shape and hold my feminine curves. After months...Read On

Added: 05 Apr 2015 | Category: Crossdressing | Avg Score: 4.85 | Words: 11,068 | Tags: sex  head  blow job  suck   | 5 Comments

tvk3983

All The Way (Part 3)

Brenda goes the distance

When I awoke it was later than usual but considering the fact that I'd been through back to back fuck marathons in as many nights, I thought it wasn't bad. Slipping out of bed I stepped into a robe and went to the potty, before looking at myself in the mirror. I was a mess so I took the time to freshen up my makeup, washing some off before putting any more back on. Satisfied with how I looked,...Read On

Added: 04 Apr 2015 | Category: Crossdressing | Avg Score: 4.22 | Words: 9,299 | Tags: anal  crossdressing     | 5 Comments

tvk3983

All the Way (Part2)

Kathy and Brenda go out

When Michael stepped inside and closed the door, he gave Kathy the same kind of kiss as his wife had. He was quite an imposing man; short cropped blonde hair, very piercing pale blue eyes, a little over six feet tall and built sturdily, weighing somewhere around two hundred pounds. My heart skipped a beat when I took in the complete picture. Now I wondered how Kathy would convince the woman...Read On

Added: 30 Mar 2015 | Category: Crossdressing | Avg Score: 4.93 | Words: 8,202 | Tags: anal  oral  crossdressing     | 7 Comments

tvk3983

All the Way (Part 1)

Kathy makes Richard pay the price

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. ...Read On

Added: 21 Mar 2015 | Category: Crossdressing | Avg Score: 4.82 | Words: 7,352 | Tags: crossdressing  anal  oral  strap on     | 19 Comments

showit4u

Meeting my Ex-Girlfriend's New Boyfriend

being seduced at the bar

Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and...Read On

Added: 21 Mar 2015 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,794 | Tags: lace panties   | 9 Comments

thatfemininUrge

Going Down

the fun of making it spurt

I have always enjoyed my transformation into a woman when the urge for me to dress en-femme struck me. I would become excited at seeing my body, suddenly become curvy and feminine. It was not just a physical change in me. It was also a mental change. I became less aggressive, and I wanted to be dainty and soft. Naturally, it would al begin as I padded and cinched my body to become curvy. It...Read On

Added: 05 Mar 2015 | Category: Crossdressing | Avg Score: 5 | Words: 9,124 | Tags: blow job  oral  head  sucking cock   | 10 Comments

showit4u

The Meter Reader

Caught Wearing My Bikini

I'm basically a 'city boy' but one summer decided to rent an old two story farmhouse in the country. It had its good and bad points. The bad was that it was quite a way from town. I was working nights at a bakery and had to drive the twenty or so miles to work in the dark every night. The good part was that it was secluded. I could walk around the house in just my bra and panties, a short...Read On

Added: 20 Feb 2015 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,839 | Tags: unexpected visitor   | 15 Comments

jstephens

Taking Another Step

More than just words as we take another step toward our ultimate fantasy

It had been nearly a week since the scintillating Saturday when my fiancée and I had the most incredible meeting of the minds about our sexual desires. Unfortunately, as the days crept forward from that fateful afternoon, I began to worry that those moments were an aberration rather than a sign of things to come. In the throes of passion, we had done a bit of internet browsing for the...Read On

Added: 15 Feb 2015 | Category: Crossdressing | Avg Score: 4.86 | Words: 975 | Tags: sex  strap-on  panties  hetero  lesbian   | 8 Comments

SosaGood

My Mother's Boyfriend, My Slut

He seemed like a slut to begin with, who knew he really was.

 Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought...Read On

Added: 14 Feb 2015 | Category: Crossdressing | Avg Score: 4.71 | Words: 1,943 | Tags: toys  cross dressing  collar  leash  crop   | 15 Comments

jstephens

Laying the Groundwork

Extending the boundaries with my fiancee

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a...Read On

Added: 06 Feb 2015 | Category: Crossdressing | Avg Score: 4.76 | Words: 752 | Tags: sex  anal  strap-on  crossdressing   | 11 Comments

Dinata

A Night at the Ambassador

An early evening of debauchery earns kudos for a crossdresser.

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were...Read On

Added: 04 Feb 2015 | Category: Crossdressing | Avg Score: 4.69 | Words: 1,405 | Tags: crossdressing  stockings  heels  blowjob  fingering  theater  cinema   | 6 Comments

Dinata

Bookstore Crossdressing

Giving Up My Butt-Cherry

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. ...Read On

Added: 27 Jan 2015 | Category: Crossdressing | Avg Score: 4.7 | Words: 1,519 | Tags: anal male  crossdressing  bookstore  nylons  heels  gloryhole  booth   | 18 Comments

fitzythemartian

Married Crossdressing Fun Ch. 3

Mikki takes a new direction

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She...Read On

Added: 26 Jan 2015 | Category: Crossdressing | Avg Score: 5 | Words: 2,394 | Tags: lingerie  married  possible infidelity  anal   | 4 Comments

showit4u

My New Neighbor

Slender cross dresser can't resist well-hung guys.

I'm a slender, thirty-two year old, bi white male. I've been cross dressing since my teens and love the look and feel of wearing women's clothes. I'm not into all the heavy stuff like wigs, breast forms, padding etc. I mostly wear lace panties, bras, lingerie, garter belts, sheer nylons and heels. I was blessed with long legs, a slim waist, nice round hips and a very shapely little ass. As...Read On

Added: 26 Jan 2015 | Category: Crossdressing | Avg Score: 4.84 | Words: 1,958 | Tags: blowjob   | 8 Comments

showit4u

A Summer Night Cruise

Bi Cross Dresser Showoff

I'm a thirty two year old slender, leggy, well-hung cross dresser. I've been wearing panties since my teens and probably always will. The feel of sheer nylon panties covering my cock and hugging my girly little ass makes my eight inches rock hard the minute I slip into them. The only thing better than jacking off while wearing them, is letting another guy do it for me while I'm pleasing his...Read On

Added: 15 Jan 2015 | Category: Crossdressing | Avg Score: 4.61 | Words: 1,709 | Tags: lace panties   | 16 Comments

fitzythemartian

Married Crossdressing Fun Ch. 2

The relationship moves forward

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was...Read On

Added: 14 Jan 2015 | Category: Crossdressing | Avg Score: 4.57 | Words: 1,608 | Tags: bi  group  married  wife   | 2 Comments

vanessagrrl

Christmas Shopping

My favorite thing about the holidays is that I can freely shop for lingerie without feeling nervous. Plenty of guys buy sexy underwear for their wives and girlfriends so there is always a feeling of freedom at this time of year to shop and take my time. I could really spend hours in Victoria’s Secret looking at all of the pretty, lacey thongs, boy shorts, bras, and garters. On this trip I...Read On

Added: 11 Jan 2015 | Category: Crossdressing | Avg Score: 4.74 | Words: 1,514 | Tags: crossdressing  oral  anal     | 11 Comments

fitzythemartian

Married Crossdressing Fun Ch 1

Caz and Michael's marriage changes direction

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She...Read On

Added: 11 Jan 2015 | Category: Crossdressing | Avg Score: 4.36 | Words: 7,381 | Tags: bi  group  married  wife   | 3 Comments