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ThePhantom

Crossdressing

33
vote
TaraNicole

Six Months

A girl's dreams cum true

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he...Read On

Added: 03 Oct 2012 | Category: Crossdressing | Avg Score: 4.87 | Tags: transvestite  crossdresser  stockings  anal  oral   | 9 Comments

48
vote
bethanngirl

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

Added: 03 Oct 2012 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  skirt  masturbation   | 11 Comments

3
vote
CourtneyFux

Girlyboy Gone Wild - Part Six

After being a sexy school girl, I become Fifi, a sexy French maid.

With both of my hands wrapped around Dan's big 11 inch cock, I felt just like a little girl in his classroom. I jerked him off with both hands while I sucked on the head of his cock, getting it ready for him to put in my tight little girly ass. I licked around the big head of his cock, smelling my sticky-wet, cum-soaked white cotton panties he was wearing. Oh, it was all so kinky and fun...Read On

Added: 02 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  oral sex  voyeur   | 2 Comments

4
vote
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 | Tags: crossdressing  oral sex  voyeur   | 2 Comments

4
vote
CourtneyFux

Girlyboy Gone Wild - Part Four

At my panty party, I get to suck four big cocks in one night.

Being a slutty sorority girl having sex with my professor was really fun. I was sitting in his lap with my back to him with his big 11 inch cock between my freshly-shaved legs and rubbing it against my hard clitty dick. My little white cotton panties were soaking wet in front with pre-cum. My teacher was playing with my titties while I stroked his big one. "I'm going to take your bra off,...Read On

Added: 30 Sep 2012 | Category: Crossdressing | Avg Score: 4.5 | Tags: crossdressing  oral sex  voyeur  

7
vote
CourtneyFux

Girlyboy Gone Wild - Part Three

Playing dress up for men at my panty party is lots of fun.

With my little sexy blue plaid school girl skirt pulled up, I leaned over the desk for teacher Dan to spank me. Dan reached down and pulled down the back of my little white cotton panties revealing my very sexy ass. I saw how big his eyes got when he saw two of the sweetest cheeks he ever saw. He looked up at me. "You have a nice butt on you, Courtney." I smiled. "I hope I get to sit on...Read On

Added: 29 Sep 2012 | Category: Crossdressing | Avg Score: 4.71 | Tags: crossdressing  oral sex  voyeur   | 4 Comments

6
vote
CourtneyFux

Girlyboy Gone Wild - Part Two

The panty party weekend brings new boyfriends into Courtney's life.

It was very flattering when Bill told me I have a hotter body than his ex-wife. Since it was his first time with a girlyboy, I knew he was being honest. A more experienced gentleman might have said it just to be nice. But Bill really meant it. In fact, he said his cock was already hard for me just from seeing my nice ass poking out of my turquoise thong. Bill was my 7:30 date, then I had Dan...Read On

Added: 28 Sep 2012 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  oral sex  voyeur   | 5 Comments

12
vote
CourtneyFux

Girlyboy Gone Wild - Part One

An all-weekend party in my panties leads to lots of sexy pleasure for the boys.

Wearing sexy lingerie for a man is my favorite way to feel like a girl. I've been doing it since I was 16 and have never been shy about it. Every few months, I get the urge to do it. So, this month I did it again. To find men to turn on with my sexy lingerie, I placed an ad on the local dating line: "Hi. I'm a hot girlyboy who likes older men. I'm having a party in my panties this weekend and...Read On

Added: 27 Sep 2012 | Category: Crossdressing | Avg Score: 4.42 | Tags: crossdressing  voyeur  oral     | 7 Comments

34
vote
kyliekained

The Adult Theatre

A true story with the name and location changed for a good lush friend.

I got to the hotel early so that I could get myself fully prepared to meet a guy I had been chatting with via a chat room. I decided to wear my favorite pink check mini skirt with my sexiest pink undies to match. I added a white silk blouse and a white garter belt with some white stockings. I took time applying my make up, making sure I had dark sultry eyes and perfect red lips, I wanted to...Read On

Added: 20 Sep 2012 | Category: Crossdressing | Avg Score: 4.78 | Tags: crossdressing  oral sex  anal  strangers.   | 8 Comments

19
vote
kyliekained

The Party

After two visits to Bill's I had been invited to a party.

Here I was nervous as anything at the railway station, I had just phoned Bill to tell him that I was on my way as promised. The journey itself was uneventful and I arrived in the next town on time. I walked out of the station my nerves getting worse and scanned around the people all milling around. I couldn’t see Bill and started to worry, my eyes were drawn over to a woman walking towards...Read On

Added: 18 Sep 2012 | Category: Crossdressing | Avg Score: 4.74 | Tags: crossdressing  anal  oral  spanking  group sex   | 7 Comments

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harrylime

The Substitute Soul-Mate

She spanked me hard and pulled my cock back to my ass stroking until I had to go.

THE SUBSTITUTE SOUL-MATE Obsessions are a funny thing. People, who are obsessed beyond the bounds of all logic, seldom are aware that they are a prisoner of their own twisted desires. In fact, in most cases, when confronted with the reality of their unhealthy emotions, obsessed individuals shrug it off as jealousy or bias or some other motivation, except, just telling the truth. In...Read On

Added: 15 Sep 2012 | Category: Crossdressing | Tags: crossdressing  anal  oral  toys  group  bisexual  masturbation   | 8 Comments

22
vote
kyliekained

My second visit to Bill's

This is the second part of Picked up in the toilets.

Here I was waiting to meet Simon, I had turned up an hour early. God I was keen after the week before, I just wanted more of the same. My mind whirred over wondering how many cocks I would suck and whether Debbie would suck me again. Would she tie me up this time? I just couldn't wait. Eventually Simon pulled up at the arranged place just like he said he would. I got into the car and we set...Read On

Added: 11 Sep 2012 | Category: Crossdressing | Avg Score: 4.9 | Tags: crossdressing  bdsm  spanking  trans  anal  oral   | 8 Comments

18
vote
NaughtyAmy

My first time outdoors

My first time dressed outdoors for sex

It had been about a year since my first time with a man and I had been with a couple more since. They were enjoyable experiences but I had failed to capture the thrill of the first time. I had continued to talk to guys online and a lot of them were trying to convince me to go for a drive with them to a secluded spot for some risky sex. I was reluctant for several reasons but the fear of...Read On

Added: 11 Sep 2012 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdressing  latex  anal  oral  outdoors   | 6 Comments

28
vote
DeedraCd

The Change Up - Part 4 - Tower Chair

Deedra shows how big a slut she is and becomes a member of Elsie’s VIP club!

Looking through the sheer curtains of the cabana, I see about a dozen people looking at both of us. Some I just met tonight and others that I don't recognize. Then Emily says to me, "Since you been a naughty cum slut again, I will have you service some of the VIP members tonight! Remember don't talk to anyone and only whisper into my ear." Cuddling next to Emily, I think back to the...Read On

Added: 10 Sep 2012 | Category: Crossdressing | Avg Score: 4.88 | Tags: group  oral  spanking  anal  crossdressing     | 8 Comments

2
vote
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 | Tags: transvestite  slut  leather  bisexual  roleplay  thigh boots  swingers  

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