Dude01's stories
01 - Bound and Crossdressed by My Friend
Story index at the bottom
By Dude01
Monday June 25th 2001 02:37:58 PM
Bound and Crossdressed by My Friend
My name is Tom and I'm 16. I have an interesting story about how I was crossdressed and bound. The friend's name is Karen and she's 15, 5'6, blonde hair, blue eyes, and a cheerleader. She's pretty attractive, but we're mostly friends so I try not to look at her that way. I'm around 5'10 with brown hair and eyes.
I've always been kind of curious about girl's clothing, but never had the courage to actually try it until this experience. The whole ordeal started with a pleasant chat conversation. I won't write the s/n's because I want to keep her privacy an issue, so here's the convo:
Karen: What are you doing today?
Tom: I don't know..watch tv?
Karen: cool
Tom: What about you?
Karen: I might go to the store and get some underwear and pantyhose..you know, girlie stuff
Tom: really? would you mind picking me up some of that? I am in desperate need...jk
Karen: no problem, I'd be happy to! lol
Tom: lol
Karen: I have an outfit that would go perfect with the underwear and pantyhose too
Tom: you don't say?
Karen: Yeah, you should come over and try it on
Tom: are you for real?
Karen: yes, it would be fun...it'd be fun to give a guy a make-over. C'mon tommy...
Tom: hmmm...well, I don't know
Karen: Come over this saturday around 12. My parents are going away for the weekend so i have the house to myself. this is the perfect opportunity, c'mon.
Tom: maybe, I'll see
Karen: Great, and ask if you could maybe spend the night too
Tom: alright
Karen: hee hee, this will be so much fun
Well, that was the extent of our conversation. Don't worry, there is bondage in this story. Four days later I found myself driving to her house. My parents knew her and her parents so they were ok with me spending the night. Plus, they thought her parents would be home...Anyway, when I arrived at her house she was waiting on the porch. I thought maybe she had forgotten, but no. I wanted to do this, but really nervous about doing it too. She came out and told me to hurry inside and go to the bathroom because we had a lot to do. I could only imagine what else she had planned. So it was just a make-over...can't be that bad, right girls? That's what I thought...
I went into the bathroom and she was standing there. She pointed to the elctric shaver first, then the razor. I figured it out and started to walk away, but then she came up behind me and cuffed my hands before I knew what happened.
"What are you doing?!" I shouted.
"You're not cooperating. Now, you can either stay in those all night and have me do this," she said as she began to tickle me. (She knew I was really ticklish from being my friend and all.),"or you can be a good boy and get yourself ready. It's not that bad, ok? I won't think you're less of a guy for doing this. This is just something fun we're doing. No one has to find out about it either."
I didn't want to spend the night getting tickled to death, so I decided to just go through with it. Besided, I wanted to try it out anyway...I only acted like I didn't because I didn't want her to think I wanted to. Was that confusing? Sorry. She left the bathroom and I was alone. She gave me more instructions by yelling through the door. I used the electric shaver to cut off the long boy hairs and then used the razor to shave off the little stubbles. Then, she said to put lotion on my legs so they didn't dry out, since this was my first shave. Finally, after about half and hour give or take a few, I was done. It took longer than I thought. Then came the next suprise...seeing what outfit she had picked out. I went in the room and that is where I saw the array of things laid out. There was a plaid skirt, blue blouse, bra, panties, a wig, and tan pantyhose. She turned around so that I could put the majority of the items on. I had trouble with the bra and panythose, but after a few tries I had it all on. Then she gave me two waterballons for..you know. Then, she adjusted the wig and put on the make-up and did my nails and found shoes. I was finally all dressed up as a schoolgirl. Then it happened...
"Ok, now what?" I asked.
"Lay down for a second," she said in a soothing voice.
Now, I should have known this wasn't a good idea, but I did as she said. I laid down and heard a couple noises, but didn't pay attention to it. I was too busy feeling the sensation of the clothes. Honestly, I began to like it. After not having worn anything like that at all, feeling it for the first time was kind of cool. Anyway, about what happened...she turned me over on my stomach and straddled my back. I began to ask what was going on, but then she stuffed something in my mouth and taped it shut. I was about to reach up to my mouth to rip off the tape, but then she pined my arms and taped them together at the wrist. I was really squirming, now. Then, she taped my ankles and knees. After that, she turned my over and taped me above and below my 'breasts' and my waist as well. I couldn't move.
Then she spoke, "I knew you wouldn't have let me keep you like that for much longer, so now I have to do this. Don't worry..."
She stood up and took out her camera. Doing this just us and that was it was one thing, but doing this and taking pictures was another.
"This had been so much fun, I just want to make sure we can do it again sometime. I'm sure you'll understand."
Then the tickling began. She began at my sides and worked her way down to my feet. I don't know if it was the pantyhose, but my feet were so tickles. I squirmed and wiggled, but it was no good due to me being taped up. She ran her long nails up and down my pantyhosed feet and across, side to side. I screamed into the gag, but it was no use. She was in her own little world of control. She sad on my legs facing my feet so she could tickle them with out me wriggling away. She tickled my feet for a half hour straight and I was about to die. Finally, she ended my torment for a while and flipped on the tv in her room.
Then she spoke once more, "Don't get too comfortable. Remember, you're here all night..."
If you want me to post the events of the rest of that night, I will do so. But, if you think what I wrote was already enough, that's cool too. Just give me some feedback as to what you want. Thanks for reading.
Dude01
Wednesday June 27th 2001 12:05:26 AM
Bound and Crossdressed by My Friend(2)
Well, since I got some good feedback on my story, I guess I should finish it. I wouldn't want to leave you all hangin, now would I? Ok, so when I left off I was dressed up as a schoolgirl and taped by my friend, Karen. She had just gotten done tickling my pantyhosed feet and turned on the TV. She said it was dinner time so she ordered a pizza. I was left up in her room taped like that and gagged until the pizza finally arrived. She opened the door to the room.
"Well, I was worried you might have ran off," she said with a smile.
She came over to ungag me. She ripped off the tape, ouch, and then pulled out what had been in my mouth. It was a pair of panties. "Don't worry, they're clean, Tom. Hmm, I'm going to have to figure out a name for you because Tom just isn't working with that outfit. How about...Tina?" she asked. "You are enjoying this a lot, aren't u?" I asked already knowing the answer. "Oh yes, this is so much fun. I can't do this kind of stuff with my girlfriends or boyfriends."
"I see. So I'm guessing this is something we'll be doing a few more times, huh?"
"A few? No, we're going to be doing this a lot more!"
Now, most guys would look at this predicament and ask, 'Tom, why did you get yourself into this? Any guy with any ounce of dignity wouldn't let a girl dress him up like this and tape him so he couldn't get undressed or get away. Why would you put up with this?' You know what the answer to that question would be? It would be this, 'I don't know. I've never done it before and it's a little fun and seems to get more fun. But, the real answer is I don't know.' Before I get back to the story, I have a quick question. How many guys in here have or would like for this kind of experience to happen to them?
Anyway, she fed my pizza and helped me drink my coke while we watched a movie. Afterwards, she helped me stand up and hop over to the bed. She made me promise not to fight back or anything once she undid the tape. She undid it and instantly handcuffed me to the bed. I knew she was going to do something, but I kind of wanted to see what it was she was going to do. She didn't gag me...instead, she did a few things I can't mention here on this forum, but it was quite enjoyable. Then, she started tying my wrists to the headboard until they were securely tied. Then, she took off the cuffs and tied my ankles to opposite sides of the bed. Finally, she gagged me again...this time she used a pair of dirty panties and I glared at her. She told me if I could get myself out in an hour, she would let me tie her up for the rest of the night until 10 the next morning. I couldn't really argue because I couldn't talk or move. I began to wrestle the ropes. Saying I wrestles the ropes was hardly what it looked like what I was doing, though. I squirmed and struggled, but I only succeeded in making my skirt rise several inches up my legs. I realized I wasn't getting out. She had used too much rope in a very strategic way. All I could do was wait and occasionally struggle with the ropes. Finally, she came back and looked amused. She tickled my helpless pantyhosed feet again and moved up my thighs to my ribs and then back down to my feet again. She tickled them off and on for the next several hours while I screamed and wailed into the gag. She never got tired of seeing me squirm and hearing my squeal like the sissy schoolgirl I had become.
Somewhere along the way, I had began to enjoy the experience. I had been interested in bondage long before this experience, but not crossdressing as much. I didn't realize the two could fit together and produce the experience I had. There is no way to feel more helpless and not in control while tied up in girl's clothes by a girl. When she finally tickled herself out, she climbed into the bed and fell asleep on me. She woke up occasionally to check on my bonds and to make sure I wasn't in danger of losing a limb. By morning, she decided I had had enough and let me go, but told me I had to wear the uniform for a while longer around the house. I did and we talked and hung out and that was that. I did get my revenge one day, but that's another story. I hope you liked this as much as the first part. The first part was more interesting, but oh well. Tell me what you think. Thanks for reading.
Dude01
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