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Crossdressing

21

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with. She would drive me crazy when she donned a pair...Read On

8

Ladies Night at the Leather Bar Part 1

Lingerie Love in the Land of Leather

Chloe McGill never led me astray. I was a fulltime, tax paying citizen of Astrayville long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl has ended up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gangbangs and sexual trysts of all sorts and sizes.  She is the...Read On

27

becoming a cock worshipper

I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes.  I especially enjoyed watching a girl choke and gag and cover a hard cock in her spit. I also realized that my favorite scenes always involved a...Read On

4

The Best of Both Worlds 2

"Oh, God, Daniel!" Arya cried out in ecstasy, as her body came to orgasm. Sitting on top of Daniel, she let her body bounce on him, as he shot a load of cum into her with every upward thrust. She screamed excitedly with each push that Daniel gave until he was finally finished, and Arya rolled off and lay beside him. The sex had been both exhilarating and disappointing. As always, it...Read On

2

Sissy Blane in the Hart of the Valley

Having had the first date with Plumrose, Blane visits a t-girl club with Cindy

When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persevered and undressed properly, removed all makeup and even put my wig back on its wig head. But when I was finally between the covers my brain refused to cooperate, rethinking the night's events, imagining how they may have looked...Read On

9

Taking That First Step. Part 5.

Lana began to protest at being pulled toward the bed; she felt she had been punished enough. Her ass was on fire due to the spanking she had just received. Her protests were ignored. Lana was pushed face down on the bed and she felt Cassandra sit on her back before she could attempt to rise. She felt Cassandra attach something to her wrists. Lana opened her eyes and saw restraints....Read On

5

Special Soiree

The two sissies meet for their special party

“Amanda” was fully dressed when “she” opened the door. She almost shyly greeted her close friend “Suzette.” “Hi Suzette. It’s been a while,” Amanda said. Suzette had an unhappy expression on her face. “I know, too long.” Then she looked around clearly nervous. Amanda knew that sensation, and opened the door wider. “Please, come in.” “Thank you, Amanda,” Suzette said her confidence...Read On

19

Wife Gets Even - Chapter 1

A husband takes advantage of his wife over a bet but the wife gets a chance to turn the tables.

My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking....Read On

7

Taking That First Step. Part 4

Lance gets fully dressed.

It had been a long week for Lance. He didn't think the weekend would ever arrive. It was his summer job and kept his mind occupied during the seemingly endless days. He worked for a small company in their shipping department. The job was not very glamorous, but it paid well and kept him clean.  Even as we worked his mind thought about what Saturday would bring when he visited Cassandra's house....Read On

10

Taking That First Step. Part 3

Lance's transformation continues

Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen.  Upon exiting Cassandra reappeared...Read On

8

Two Cross-dressing COCK SUCKERS

It was a somewhat long and wide almost horseshoe shaped semicircle line that contained seventeen different men either bare ass naked or with full-frontal open-fly cock exposure that special Friday night last Dec. 24th. Yes, it was the finals of our Private Gay Club's BEST 2004 COCKSUCKER OF THE YEAR CONTEST. Just like each of the eleven preliminary monthly contests held before it, the rules...Read On

15

Taking That First Step. Part 2

Lance returns to the specialty shop

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room. Once in his room with the door locked behind...Read On

15

Further Exploration

Shauna and Jerry make a video.

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s...Read On

6

Jenny & Mike: Romantic Picnic

A nice romantic picnic that culminates into public pegging.

It was close to 10 a.m. and I was still in bed with Michelle sleeping peacefully next to me. Last night had taken quite a bit out of me. Having been used and fucked by two cocks was a huge turn-on. ‘Mike’ and ‘Carlos’ had given me quite a workout! I received the fucking of a lifetime. Sex with Michelle had always been great, but having a third person added a totally different edge. The...Read On

26

Taking That First Step

A story from the seventies

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop,...Read On

10

Sharing Jessica With Nick

We introduced Nick to Jerry's secret, leading to one hot evening in preparation for his initiation.

Jennifer and I sat at my kitchen table on Saturday afternoon sipping beers following our fuck fest with Holly and Nick the night before. Jennifer didn’t have to worry about picking up her kids until Sunday late afternoon and Jerry wouldn’t be home until later Sunday night. We had both woken up late that morning and just now sat down to chat about what happened the night before. Jennifer...Read On

Saturday With Al

One of those rare days with a new lover that doesn't disappoint.

After a great night of sleep, I awoke Saturday morning thinking of spending the day making love to Al. After coffee, I drew a nice hot bath and proceeded to spend the next thirty minutes getting clean and smooth. After drying off I applied liberal amounts of a lavender-scented lotion to keep me soft and smelling nice. I also made sure that my feet were quite soft as well, since that seemed...Read On

15

Never go into an alley

Pulled into the alley behind a dumpster

It had been months since I had the opportunity to dress En-Femme. With so much time having passed and not being able to indulge my feminine needs, I was about to explode. The tunnel was long and dark to fulfill that need, but I knew that at the end of it would be a light. Not realizing just how long that tunnel was, I had purchased a new blonde wig, a new pair of tight, low hip riding...Read On

28

Changing Room

I had finally worked up the courage to explain to my wife that I liked to wear panties. I dressed off and on in her clothes for years, and she didn't suspect a thing. Before that, when I was single, I had taken to snatching the odd pair of panties out of the dryer in whatever apartment building I was living at the time. When I was a little boy I had always wanted to be pretty like a girl,...Read On

9

Sissy sperm bank

I started the morning my favorite way, really the only way I know how: with my bull's big cock between my lips. This was one of those nice slow blowjobs that he liked to start the day with. I made it especially wet for him today, slobbering all over his thick shaft while lovingly looking up at his eyes. I grasped the base with my dainty hands and licked the head like a lollipop while smiling...Read On

19

The Compromise - Part 2

The fantasy compromise comes with an unexpected twist.

Andre and his three girls, me being one of them, piled into his car. Andre assumed his role as the driver, Mikayla grabbed shotgun, and my wife, Ally, and I got into the back seat. My heart pounded in my chest with nervousness, as this was my first time going out en femme. Ally no doubt saw the fear in me and scooched closer, taking my hand in hers. "Baby, don't be scared. We're just a...Read On

27

Daddy not Dad

I found out what by stepfather and his buddies were up to...

I discovered my bisexual inclinations fairly early in life, so by the time I was nineteen, I had done nearly everything you could do with any combination of genders and numbers. I'm a regular guy on the outside, but in private I am comfortable in both the masculine and the ultra-feminine role. I could pass on the street as a hot, high-heeled slut, blowing straight guys in their cars, or...Read On

It Wasn't Love But It Sure Felt Good!

Some nights just don't turn out like you thought they would.

Al called me first thing Saturday morning to express how much he enjoyed our time together last night. He also asked if we could do it again soon. I told him that we could this coming Friday if he was available. I could show him some of my other outfits and the pictures that he took of me as well. He gleefully responded that it was a date. As the week progressed ever so slowly, we spoke...Read On

4

Sissy Blane and the Hydraulic Inevitable

Blane finally has an encounter with Mr. Plumrose, the first installment to pay off a debt .

The story so far: debt-ridden Sissy Blane's first obligatory date with Mr. Plumrose is about to take place.   '...there's nothing good or bad, but thinking makes it so.' The truth of the old saying occurred to me as I awoke on the fateful Friday and was surprised to discover that I was looking forward to the events of the coming evening. Arising from my bed feeling energized I...Read On

26

First time for 'Everything'

First time out crossdresser gets lucky with trucker.

My story is like so many I have read before and which I only fantasized about, till now. This story is all true. I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first. I have been crossdressing for as long as I can remember, from sneaking a pair of my sister's knickers, to sneaking into...Read On

6

The Best of Both Worlds

Daniel had known from the start, what he was risking when he entered into a relationship with Arya.  There was a reason the woman had never settled down with any one person.   Always open and honest about her sexuality, Arya was bi with an equal level of attraction to both sexes.  She was also very sexually active, always telling her friends that she would never settle down with anyone, as...Read On

An Unexpected Love Story

What was supposed to be a night of dressing turned into a night of making love.

I was so looking forward to Friday. My latest order of lingerie was scheduled to be delivered and knew that I would have some time after closing to try it all on. I own a small business and I work alone on Fridays for this very reason, it gives me time to indulge my secret passion. Getting dressed really helps me relax after a stressful week and have a back room where I can also take pictures....Read On

29

I Just Wanted a Kiss

I was pretty high and told Mike what I needed.

Mike and I had been working together at Tony's Pizza for about a year. We were both twenty-two years old and we were both losers that didn't give a fuck. I lived at home in the room where my mom had changed me and tucked me in, I saw no need to move on. Mike lived in his sister's basement since his parents had kicked him out. We were both pot heads and we made enough at Tony's to buy some...Read On

10

A Night of Firsts pt 3

Pam has a first

We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh. I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me...Read On

10

From inside to full time

Debra moves from hiding to living full time

With the changes in my persona, there were a few in Tina’s. Again, not massive earth shaking changes but changes none the less. One of them was how we interacted especially in public. We were more like friends than a couple. No one would have been able to notice anything other than two people that knew each other really well. I once asked her about how she was acting.   Tina stated, “Well,...Read On