Crossdressing

cassandrababy

Adventure in St. Louis

Cassie's adventures on a night in St. Louis

A NIGHT IN ST. LOUIS Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make...Read On

Added: 18 Jan 2011 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  anal  oral  quickies   | 9 Comments

ChelseyR

In Wonderland, Pt. 3

'Tilly' spent the night at Chris Smith's house, waking to find it impossible to avoid Leila Smith, a friend, peer and beauty queen. She was not best pleased about the situation, but helped to protect Tilly's true identity in lending out a girls uniform, one purposefully as feminine as she owned. Chris was just about to give them a lift to school... I shuffled down the stairs,...Read On

Added: 08 Jan 2011 | Category: Crossdressing | Avg Score: 4.78 | Tags: crossdress  schoolgirl  kiss  alice  found out   | 2 Comments

salidin

A weekend with Nancy: part 2

Nancy, that was the best blow job I ever had, she's awesome, Dan replied.

 Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any...Read On

Added: 02 Jan 2011 | Category: Crossdressing | Avg Score: 4.8 | Tags: buttplug  heels  corset  collars  blowjob   | 1 Comment

webbyhose

Becoming an Escort

The nights second cock spurted hot sticky cum on my face and I greedily pushed into my mouth faking my enjoyment of that bitter taste. My “lover” dressed and left the room. I lay back on the bed where two men had fucked me that night and pondered how I had got into this position. Despite myself my cock was rock hard in its silk panties stained with my own cum. 3 weeks earlier I had told...Read On

Added: 30 Dec 2010 | Category: Crossdressing | Avg Score: 4.46 | Tags: gay  feminisation  first time  anal   | 7 Comments

salidin

A weekend with Nancy

It was staggering to think that it was only 8pm and Nancy was to be with us the entire weekend

  CHAPTER 1 Upon arriving home from work one Friday afternoon my wife informed me that the kids would be staying the weekend at some friends house, and that she had made some special plans for us. She then went on to say that she would be gone for a couple of hours and that while she was gone I was to shower and to shave myself from head to toe. Then I was to get my...Read On

Added: 28 Dec 2010 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  threesome  enema  strapons   | 4 Comments

Pamala2000

Pamala's first adventure

This happened to me years ago when i was in the Army

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101...Read On

Added: 07 Dec 2010 | Category: Crossdressing | Avg Score: 4.94 | Tags: crossdressing  sex  anal   | 18 Comments

baldie

My First Time

Fist time oral

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy...Read On

Added: 05 Dec 2010 | Category: Crossdressing | Avg Score: 4.88 | Tags: oral  gaymale  crossdressing   | 6 Comments

Karin

The Worm Turns Part 2: The Routine

After establishing a routine, a surprise visit by a man took my tranformation to a new level.

Before I even realized it, we had fallen into a pattern of visits to the sisters’ salon. On a weekly basis, I was having my hair set, my nails done, and my make-up applied expertly by some combination of Kim and/or Kristie. Often one would do the work while the other recorded the proceedings on video or with a digital still camera. Several of the photos made their way onto the mirrors of...Read On

Added: 22 Nov 2010 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  blow job  beauty salon   | 2 Comments

ChelseyR

The Guest

Is this in the job description?

"Do you want to keep your job or not?" She asked me. These were desperate times, I was up to my eyeballs in debt and bills, and the job at hotel was all I had. She had threatened to get me fired. I thought back to the beginning of this, wondering how I had got here. Slightly earlier "The lady in room 404 just called to say she had some kind of trouble with her wardrobe door,...Read On

Added: 22 Nov 2010 | Category: Crossdressing | Avg Score: 4.33 | Tags: hotel  guest  concierge  blackmail  tutu  ballet  leotard   | 2 Comments

Suzy

Audrey

True account of a night out.

The people involved in tonight’s tale are, Anne, her god-parent Audrey, and myself. A few weeks ago, Anne told me about her god-parent Audrey getting ripped off by the guy that was living with her. Apparently he’s been seeing someone else after moving in with Audrey for a year or so. During that time he’s persuaded her to buy a bigger house and get a mortgage to do so. Then things...Read On

Added: 19 Nov 2010 | Category: Crossdressing | Avg Score: 3.91 | Tags: true account.  

Aimee_Cd

Pure Innocence

Well, maybe not...

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on...Read On

Added: 15 Nov 2010 | Category: Crossdressing | Avg Score: 4.44 | Tags: panties  masturbation   | 5 Comments

webbyhose

Friend's Treat

A divorced man gets a treat

I had recently split with my wife and was feeling very down. I was invited to spend a few days with my old friend Dave and his wife Tracey. The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse. I...Read On

Added: 09 Nov 2010 | Category: Crossdressing | Avg Score: 4.92 | Tags: shemale  gay   | 9 Comments

ChelseyR

Tijuana

A truly unforgettable trip.

I finished telling Mia my story, and she stared at me blankly for a minute. "Would you do it again?" she asked me. What a question. The entire meaning of hitch-hiking had changed for me now. I was standing by the roadside in the outskirts of my city, trying to hitch a ride down to Tijuana. All the cars were just speeding past me, maybe it was something about my gruff beard that put them off,...Read On

Added: 09 Nov 2010 | Category: Crossdressing | Avg Score: 4.83 | Tags: road trip  crossdress  heels  sex  anal   | 5 Comments

ChelseyR

In Wonderland, Pt. 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door...Read On

Added: 08 Nov 2010 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdress  alice  schoolgirl  blowjob  humilation   | 7 Comments

ChelseyR

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

Added: 07 Nov 2010 | Category: Crossdressing | Avg Score: 4.8 | Tags: alice  crossdress  party  halloween  teen   | 7 Comments