Friday, October 30, 2009

Halloween Shopping

In a couple earlier posts, I told you about my friend Anna who witnessed my humiliation with an escort and had cucked me with her boyfriend. Anna had introduced me to a friend of hers named Renee who was also an escort and familiar with the humiliation of sissies. In a couple earlier dates, she had paraded me around a shopping mall having me try on bras at Frederick's and trying on high heels at a couple different shoe stores.

This particular night took the cake and was one of the most embarrassing things I've done. It was a couple nights before Halloween. First I called a store (I think it was called Fashion Cents) and asked if I could try on girls clothes because my girlfriend was making me dress up. The clerk I talked to was very enthusiastic about it and told me to come in and they would be happy to help.

I was wearing back-zip jeans and platform sneakers and a slightly feminine top. When we walked into the store, I stood there sheepishly while Renee went straight to the counter and told the girls who we were. THREE of the clerks walked out with Renee, and they were smiling and giggling. Renee told them I needed a short dress, something kinda slutty. One of the girls noticed my jeans and pointed out the back zipper to the other clerks. They thought it was funny and sweet at the same time that I would wear what my "girlfriend" told me to wear.

Renee had with her a bag of underwear and shoes that I had prepared. After she selected a couple dresses, skirts and blouses, one of the clerks pointed us to the fitting rooms. Before we went in, Renee stood there and started pulling out the various items for all to see and handing them to me. "Here's your bra. Here's your pantyhose. Here's your little lacy panties. Here's your high heels," etc. in a voice loud enough to be heard by the others. Standing about ten feet behind her is one of the clerks taking it all in and smiling ear to ear. My face was red hot.

We went into the fitting room and Renee had me put on all my underwear while she laughed and called me a sissy, again loud enough that I'm sure the other girls in the store could hear. She would laugh and say things like, "Oh my GOD! Looks like you ENJOY wearing panties!" I could hear them giggling outside.

Renee had me step outside of the fitting room so they could see me in this micro-mini stretch dress. They loved how my shaved legs looked in my pantyhose and high heels. She had me put on a short denim skirt with a very sheer blouse and then she paraded me around the store looking for other things. I was so embarrassed trying to cover up my front so my lace bra didn't look so obvious. By this time there were other young women in the store and they were staring, grinning and giggling. I was totally humiliated and totally turned on.

Back in the dressing room, Renee thought up something that would make the whole scene even more embarrassing. She took one of the dresses to the counter and asked them to the remove the tags because she was going to have me pay for it and wear it out of the store. She said she was taking me over to her girlfriend's house so she could see her sissy boyfriend.

She came back and handed me the dress. She gave me my wallet, bundled up all my own clothes, and walked out. I tried to protest, but she just said in a loud voice, "Pay for your dress, and let's go!" Then she walked out of the store, leaving me wearing the clothes I would have to pay for and wear out of the store.

I waited in the fitting room for a minute or so looking at myself in the mirror. Here was this sissy wearing girl clothes, nylons and heels. No wig. No makeup. Just a pathetic sissy. I sheepishly walked out of the fitting with all the clerks and some of the customers grinning. My hands were shaking as I handed the clerk at the counter my money. She was saying that she wanted to dress up her boyfriend like this sometime. A very attractive woman customer at the counter gave me a very condescending smile and said, "It sucks to be you, doesn't it?!" I just said, yes, and she laughed.

As I walked to the door, I was saying, "I can't go out like this!" About that time, two teenage girls walked in. Both stopped in their tracks, looked at me, and laughed. One of the clerks was at the door, and asked me why my girlfriend was making me do this. I sheepishly said, "She caught me trying on her panties a couple times." The clerk gave me a mock scornful look and said, "Well, then, you deserved this, didn't you? Shame on you!"

As I hit the door, one of the clerks called out, "Come again!" She didn't know how close she was to the truth.

The store was in a strip mall. I made a bee line for my car, where Renee was waiting laughing her ass off. I heard some laughing and an "OH my God!" behind me as I tried to run in my high heels. By the time we got in the car, I was on fire with embarrassment. She drove and kept telling me what a sissy I was and how all the cute young clerks and women in the store knew what a sissy boy I was. I pulled down my pantyhose and panties and started wanking while she said, "That's right, stroke your little clitty for me, sissy fag! Moan and cum like a girl for me. Let me hear your cum like a girl. Cum in your hand so I can watch you lick up your little messy for me!" I whimpered and cried and dribbled into the palm of my hand. Renee quickly commanded me to lick up every last drop while she called me a loser. I was drained and totally humiliated.

But it wasn't over. When we got back to my room, she put on my strapon and made me suck on it while she stood in front of a mirror. She told me to look at myself in the mirror so I could see the sissy cocksucker. Then she gave me a very sound spanking until I cried. Finally, I was made to "walk the wall." She had me position myself on the bed with my ass against the headboard and my feet on the wall. I had to raise my hips up over my face so I could cum in my mouth. She again had me suck her cock and wank while she derided me. I dribbled a load into my mouth and on my face.

I still get off re-living that night.

11 comments:

Anonymous said...

Nashville Anna?

ANY cucking is a good thing!

JamieLin said...

Yes, you know I love a good cuckolding!

Little Pantyboy said...

Yep, it was Nashville Anna.

Hi JamieLin! Long time!

Sheen V said...

If only that were me!

Teresa Bowers said...

Cute story!

sissycrissi said...

Lovely story dear, so delightfully humiliating, and so wonderfully exciting! But what will I do now -- you have my little clitty so hard and wet . . .

Chaste Hubby said...

Love the post! Thanks for sharing!

herfemtoy said...

This is one of the best stories i have ever read... and i frequent all the story sites. The shopping part is my fantasy. You lucky dog.

herfemtoy
http://www.flickr.com/photos/herfemtoy/

Chrisissy said...

Really great story, would love to have a similar experience but not sure if I would be able to complete the task but in this case there would not be other options!

Anonymous said...

Oh yes, I dolled my guy on Halloween too? Becky

Anonymous said...

Ladies I have a tip, for guys who rent costumes and don't or forget too pick them up? Forced me at the last minute,to go to a thrift store put some kind of costumes together at the last fricking minute Pre Halloween party we were invited to? I'm putting together a sexy witch outfit! For him? And punishment costume a sexy from the 60s a airline stewardess uniform with spike heels added! I also made he be wearing a pointed cone bra, and a girdle hooked up to his Nylons! With nylon panties added ! Danielle.