Crossdressing

allfours

Carl, Carla and Hannah - Part 23

The stag night, and the morning after...

There was two weeks to go before Hannah and I would become man and wife. And then, although nobody else knew, we planned to live as wife and wife. In the meantime, the final touches were being made to prepare for the big day. I decided to have my stag night a couple of weeks before the wedding, and I included Tom and one of his friends in the party. Graham, like Tom, was bisexual, but it...Read On

Added: 09 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 3,726 | Tags: crossdressing  feminisation  anal  oral  threesome   | 2 Comments

kalira

Derek and Amy

Derek and Amy enjoy some time alone.

We're holed up in a nice little hotel room in the middle of nowhere. No one around here knows us and no one will bother us. Tonight's all about us. Once we get settled in I send him off to take a shower. Now that I'm sure he's busy it's time to get to work. Digging out my bag I lay out the outfit I've had prepared for a long time. The panties are black silk, as soft as butter. There's a...Read On

Added: 16 Oct 2012 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,098 | Tags: crossdressing  bdsm   | 4 Comments

allfours

Carl, Carla and Hannah - Part 20

Carla's night with Tom continues, and then Hannah has a surprise for her.

I lay down on top of Tom, and enjoyed the feeling of his arms around as he kissed me, telling me that I was great. I lay in his arms for a while, and we chatted about this and that. He told me a little more about himself, his failed marriage and what happened with a guy he met. All the time he talked in his low, sexy voice, his hands caressed my back, occasionally wandering down to the tops of...Read On

Added: 04 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,902 | Tags: crossdressing  feminization  bisexual  oral  transformation   | 2 Comments

CourtneyFux

Girlyboy Gone Wild - Part Five

After being a sexy school girl, I become a sexy Frenchmaid.

Having my clitty dick sucked by Dan really did make me feel pretty and sexy. He was really good and was able to swallow all seven inches. While he sucked me, I played with my titties while he looked up at me. I was looking down at his big 11 inch cock sticking out of my white cotton panties he was wearing. It was all so kinky, it thrillled me to be having so much fun at my all-weekend...Read On

Added: 01 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Words: 2,822 | Tags: crossdressing  oral sex  voyeur   | 2 Comments

allfours

Carl, Carla and Hannah - Part 18

An online meeting with Tom opens possibilities, and Bill shows Carla what to expect..

As the weeks went by, we got into a sort of routine. At work and for maybe a night or two during the week or when out visiting friends or family, I would be Carl, but for the rest of the time, Carla would be Hannah's live-in girlfriend. My hair grew slowly, and Hannah would style it with extensions so that I could still look fairly convincing without having to wear a wig, which pleased me no...Read On

Added: 24 Feb 2014 | Category: Crossdressing | Avg Score: 4.57 | Words: 3,535 | Tags: feminzation  toys  crossdressing  masturbation  oral  anal  control   | 2 Comments

allfours

Becoming Chloe - Part 14

The aftermath. Chloe and Vickie have a heart-to-heart.

"Shit!" I was immediately awoken by Tina's curse. I opened my eyes to see her gorgeous, naked ass fly through the door to the bathroom, so I turned to my naked wife next to me, still half asleep. "Good morning," I murmured. "What was that all about?" "She's late for work. She should be at the shop for nine and it's gone half eight." "Oh," I said as I moved to snuggle next to her. ...Read On

Added: 09 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,801 | Tags: crossdressing  feminisation  transition   | 7 Comments

allfours

Becoming Chloe - Part 9

Vickie has an 'episode' while out shopping for a bigger cock...

A few weeks later, Chloe was a regular weekend resident in our house. Once I was home on Friday evening, I would shower and shave, and then spend the rest of the weekend as Chloe. This included going out shopping and even the occasional meal out. I'd worked hard on my appearance, and especially on my voice, and now I felt confident that I could pass even close scrutiny by anyone. Of course,...Read On

Added: 25 Jan 2016 | Category: Crossdressing | Avg Score: 4.93 | Words: 2,236 | Tags: crossdressing  bisexual  lesbian  reluctance  toys  cheating  feminisation   | 7 Comments

kalira

Derek and Amy: Matt makes three

Amy's husband Matt joins the fun

My lover and my husband are in separate rooms changing into the clothing I've laid out for them. When they're finished they'll come into the library where I'm sitting waiting for them. This will be the first time they've touched each other and I'm not going to miss a minute of it. I'm sitting in a big padded chair diagonal to the door. My husband, Matt, comes in first. He looks...Read On

Added: 17 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Words: 1,574 | Tags: crossdressing  bdsm  anal  threesome   | 4 Comments

ThePhantom

The Magician's Assistant or How it began. Part 2

Ken's life changed dramatically since under going the transformation at Mistress Elaine's. His time at the gym was spent doing high reps with low weights, concentrating on his legs and rear. He added a lot of cardio and crunches and this gave him lean muscle mass rather than bulk. As a result his whole body took on a toned and sculpted look. He worked on his makeup almost every night and...Read On

Added: 20 Mar 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,397 | Tags: dress  attraction  kissing  blowjob  anal   | 7 Comments

leatherboy

Have A Good Feel, She Loves It! Part Three

The action moves to the dance floor and the delicious Linzey!

After half an hour I was ready to go again. I looked back to the days before I got onto the scene whilst I prepared to rejoin the party. I would watch the likes of Bukkake porn and say to myself “I’d love to do that” thinking that in reality I would never even get the opportunity to try it. And there I was washing my cum covered face after having two guys wank over it in the middle of a hotel...Read On

Added: 09 Sep 2012 | Category: Crossdressing | Avg Score: 3.5 | Words: 3,922 | Tags: transvestite  slut  leather  bisexual  roleplay  thigh boots  swingers  

Dividence

The Wedding Proposal, chapter VI

Reality catches up to me.

The dinner was wonderful. Tina was the sweetest sister-in-law I could ever wish for. We found that we had lots of things in common, and quickly bonded. She told me all sorts of stories about Tony, and I shared stories from my time as his friend. I had to concentrate to adapt the stories to the new ‘reality’, but as long as Tony played along it went great. He seemed a bit uncomfortable with...Read On

Added: 16 Mar 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,594 | Tags: party  dance  alcohol  fight  one night stand  anal  random encounter   | 3 Comments

Maid2frill

Mistress Sarah fucks Evie Chapter 4

The continuing story of Mistress Sarah and Evie

I knelt by the door, anxious for the arrival of my Mistress. I could feel my arse pulsing around the butt plug in anticipation of what was to come. As I knelt and waited I could smell the pretty floral scent of the perfume that I had sprayed on my neck earlier. I felt soft and girly from all the day's events. I was in a prime mode to be fucked like a sissy. Even though I was not touching my...Read On

Added: 09 Oct 2015 | Category: Crossdressing | Avg Score: 5 | Words: 3,237 | Tags: crossdressing  lingerie  mistress   | 1 Comment

allfours

Carl, Carla and Hannah - Part 22

Hannah gets a promotion, and Claire pays a visit.

A couple of weeks later, Hannah came home and told me that the rumours had been true, and Claire had been promoted. As Hannah had been at the company the longest in her department, everyone expected her to apply for Claire's old job, and the general consensus was that she'd get it. Hannah was determined to get it as well, telling me that the extra money would come in handy for the wedding....Read On

Added: 08 Mar 2014 | Category: Crossdressing | Avg Score: 4.57 | Words: 2,337 | Tags: crossdressing  transformation  feminisation  control  lesbian  threesome   | 2 Comments

sluttracy99

My Sexual Odyssey Part V: A Real Whore

A continuation of the journey described in part 4

The next morning as I awoke, I realized that in just a few hours I was to re-experience the previous day’s activities. This seemed too much too soon, but I had agreed. Of course I could always cancel, but then if I did so I would wonder how much I’d miss it and whether I would have acclimated to the frequency and intensity. I decided to just forge ahead and so I got dressed and left for...Read On

Added: 03 Jan 2015 | Category: Crossdressing | Avg Score: 5 | Words: 2,587 | Tags: autobiography  prostitution   | 5 Comments

tvk3983

Carolyn Makes Her Way (part 2)

Mike paddles Carol - Hard!

After I left the office of my former employer I went immediately to see an attorney. There were two things I had to do: one see about suing the hell out of my former employer and two: I needed to get my name changed legally to Carolyn instead of Carl. I chose this attorney because I already knew him, very well in fact, right down to the birthmark above his nice cock. He wasn't surprised to...Read On

Added: 05 Aug 2015 | Category: Crossdressing | Avg Score: 4.8 | Words: 7,595 | Tags: cd  bondage  spanking  oral  anal  pee  

allfours

Carl, Carla and Hannah - Part 21

Carla spends Thursday night with Tom, while Hannah hears of a possible opening...

A few days later, I rang Tom, this time leaving my number visible. We talked for a while, and we both agreed that we'd had a good time, and would like to see each other again. Before I hung up, we'd arranged for me to go over the following Thursday, as that was Hannah's night with Claire. Hannah and I spent the next few days thinking about the wedding, looking at suitable venues for...Read On

Added: 05 Mar 2014 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,322 | Tags: crossdressing  feminisation  control   | 1 Comment

allfours

Becoming Chloe - Part 12

A meal with a difference...

I walked through the door, and almost immediately all my resolve disappeared at the sight that met my eyes: my wife was sitting on the sofa with her legs spread wide with Tina between them, eating her out like no tomorrow! Vickie's knickers were wrapped around one ankle, and she held up her legs high to give her lover better access to her quim. It glistened in the late afternoon light with...Read On

Added: 03 Feb 2016 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,606 | Tags: crossdressing  bisexual  anal  toys  dominance     | 6 Comments

hoterotica

Steve the Crossdressing Cat Lover

Cat lovers are a breed of their own and my boyfriend, Steve, is one of them.

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please. Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land...Read On

Added: 11 Oct 2013 | Category: Crossdressing | Avg Score: 3.56 | Words: 1,132 | Tags: cats  crossdressing  wigs   | 5 Comments

allfours

Becoming Chloe - Part 19

Tina and Vickie have some news, and Chloe has an interesting evening...

You know, they say that the thing about working in a sweet shop is that you soon seem to lose your appetite for sweets. Well, working in a sex store is pretty similar experience. At first, I was amazed at the variety and array of different toys, magazines, DVD's, clothes and nick-nacks that were available. After a while, however, I began to be less and less amazed (and aroused!) by the things...Read On

Added: 27 Feb 2016 | Category: Crossdressing | Avg Score: 4.83 | Words: 3,391 | Tags: crossdressing  anal  strap-on  romance     | 4 Comments

sluttracy99

My Sexual Odyssey Part VI: A Working Girl

A continuation of the journey described in part 5

I decided to go to the club again that night, and talk to some of the people there. As nothing much happens until fairly late, I waited until an hour before midnight, then drove downtown. I entered the club and was greeted by the people who tended the entrance, to whom I was becoming a familiar sight. I looked for a table off to the side and searched for someone with whom I could converse. In...Read On

Added: 04 Jan 2015 | Category: Crossdressing | Avg Score: 5 | Words: 3,339 | Tags: autobiography  working  whore   | 5 Comments

AmandaCarrington

Toby: The Little Rascal

A follow up to "Toby's Story"

Annabelle's last minute phone call altered our plans for the evening. "You'd better come as yourself because Toby's fucking hanging about!" She sounded a tad perturbed. Maybe the fact that her son was encroaching on her 'me time,' explained her tone. Never mind the fact that I had already started my transformation. My two-week beard growth had gone, and I was in my wife's bra,...Read On

Added: 04 Sep 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,200 | Tags: crossdresser  masturbation     | 1 Comment

havingsomefun

A New Beginning (Part 3)

My first experience in public

It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement. Ellen was very much in dressing me up from...Read On

Added: 12 Aug 2016 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,274 | Tags: crossdressing  caught  outed   | 3 Comments

tvk3983

Jaime's Way (Part 3)

Jaime gets uncaged and left alone for a week - she doesn't lack for company.

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

Added: 08 Nov 2015 | Category: Crossdressing | Avg Score: 4.5 | Words: 8,895 | Tags: cd  oral  anal    

allfours

Becoming Chloe - Part 13

Ménage a trois...

Vickie sat down on the sofa and, spreading her legs wide, directed me to her snatch. I willingly let myself be guided to her most intimate parts and breathed in her womanly aroma. I wanted to savour her, so I took my time. I kissed her inner thighs, so different from Vickie's, and brushed my nose against the thatch of hair between her legs. I flattened the mass of curls, revealing her...Read On

Added: 06 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,457 | Tags: crossdressing  bisexual  lesbian  toys  dominance  oral  anal   | 7 Comments

allfours

Becoming Chloe - Part 15

An agreement is reached...

Tina's car pulled into the drive around ten the next morning. Once the front door was closed behind her, she greeted Vickie with a passionate kiss, and then did the same to me. It felt good to be in her arms again, and I knew it would be hard not to give in to her, but we needed to sort things out. The fear of losing Vickie to her had not gone away, so I needed to make sure we kept our feet...Read On

Added: 15 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,371 | Tags: crossdressing  anal  oral  toys  threesome  fff  bisexual   | 6 Comments

BadDog9

Exploration (Discovery II)

Shauna's second lover.

After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours. Not only had I...Read On

Added: 16 Sep 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,714 | Tags: crossdressing  oral  anal  coworker     | 6 Comments

tvk3983

Carolyn Makes Her Way (part 3)

Business is booming and so is his hand on her ass!

Once I dragged my tenderized ass out of bed, tender because Mike had used a cane on me last night, I dressed in pantyhose, a navy blue, loose skirt, a cream colored satin blouse, black pumps with four inch heels, and a bra. After applying my makeup I took a look at myself in the mirror, making sure I looked good enough to conduct an interview at the leather goods store we were opening in just...Read On

Added: 13 Aug 2015 | Category: Crossdressing | Avg Score: 4.86 | Words: 7,084 | Tags: cd  oral  anal  bdsm  water sport     | 2 Comments