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23

The First Time I Wore Panties and Gave a Blowjob

The first time i got to stuff my mouth with cock!

I've just slipped into a Victoria's Secret stretchy thong and have a good tent going, so I thought I'd share with you how I got started wearing panties and giving blowjobs. I found my bi-side later in life. I used to look a lot at straight gloryhole porn, where white women would slobber all over these big black cocks. It was hard to figure out my fixation on it, but eventually it dawned on...Read On

34

Chrissy's First Bookstore Trip

Chrissy's First trip to an Adult Bookstore Arcade

After my first night dressed up like a girl in my very own clothes I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the...Read On

14

My first Cross Dresser and me

My first cross dressing experience

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said...Read On

35

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

26

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my...Read On

9

Caught and the Consequences Part 3

Husband caught dressing and the wife's retribution continues

Part 3   I signed the contract and handed it back to my wife, well my Mistress now I guess.   She took it from me and said ‘Good girl’ ‘As you will have seen you are now Philippa, now go and get all your male clothes.’   ‘Can I get dressed’ I said.   She slapped me hard across the cheek. ‘When you speak it will...Read On

12

Tennis

A panty sniffer is tamed

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew...Read On

18

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...Read On

11

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and...Read On

29

How my Best friend gave me what I always wanted

My Best friend discovers my naughty little secret

The day started from me being all alone in the house for a full day. My parents and sister were out and wouldn't be home until the next day. I decided that I would give my best friend a call and get her to come over to see me, we hadn't seen each other in quite some time. She was just as eager to see me as I was her and we were both very excited as we really enjoy each other's company. Now...Read On

21

My First BJ dressed En-Femme

I needed to confess this. It is not a story, but a reality.

I only cross-dress when the urge to be feminine comes over me. I mostly have dressed privately, but that has changed. The last four years I have ventured out in public. I was curious if I could pass as a female. Little did I know then, when I first went out in public what it would lead too? It is why I am going to tell my story here. I needed to confess and to tell someone even if it is to...Read On

26

A surprise helping hand

Getting caught paid off, in more ways than one

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I...Read On

19

Jack's Little Bitch

Learning to be a girlfriend

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right...Read On

16

Caught and the Consequences Part 4

Husband caught dressing and the wife's retribution continues

Part 4   I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me.   ...Read On

14

Lingerie and Domination

Lingerie Shopping and something more

I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected. I did not think she would be interested but I had mentioned in my reply that I like to dress in lingerie — panties in particular. I met her for a drink. She was younger ( 38 ) than me and...Read On

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

21

Punished

A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...Read On

27

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I...Read On

10

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

33

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

9

Dressing up

For some reason, guys like me in a dress

This is a series of stories rather than one story. It talks of my experiences as a crossdresser. My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who...Read On

21

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

10

A Gift for Daddy

A CD Sub gives her owner a new toy...

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him. "Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and...Read On

38

Debbie's Place

A crossdresser gets more than he bargained for

My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over...Read On

25

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

22

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

21

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

45

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

33

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

31

Ray and the Halloween Party Part Two

Part two of my wild night at the Halloween party and with Ray...

   When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....Read On