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My Girlfriend Dressed Me In Her Clothes

I was going out with a girl named Helen, who had witnessed an embarrassing bare bottom spanking from my father a year ago. When she saw this, she began spanking me too. At this point, I knew how much I secretly enjoyed this treatment and I guess that Helen was getting a bit bored. We obviously had to play it safe, since we couldn't let anyone find out what was going on. It had been going for a year now and honestly, we had just ran out of ideas to keep it fresh.

One day, I was at her house and her parents weren't around. I asked if she thought I earned a spanking and she just shrugged. The spankings had become much less fun and she didn't put as much force into them, so it was no surprise when she acted like this. I told her that I was going to use the restroom. When I got in there, I noticed a pink pair of panties on the ground. Helen was an only child, so I figured that they must have been hers. I picked them up and stared for a bit. Then I heard Helen say, "What are you doing with my panties, *****?" I turned and dropped them. I was speechless. She picked them up and told me to undress. I quickly obeyed and I was soon naked in front of her with a throbbing erection. "So...you do like them," she said. She helped me step into them and gave my bottom a pat afterwards. Unfortunately, her panties were a bit small on me and my erection stuck out. This made her giggle a lot.

"You naughty boy, dressed in my panties, what's wrong with you?" I hadn't fully caught on yet, so I remained silent. "Well, I suppose you like wearing them, don't you? You might as well wear a full outfit then!" She dragged me upstairs and brought my to her room. She completed the outfit with a pink bra (stuffed with tissues), a red summer dress, and red high heels. She finished up with makeup, including bright red lipstick. When she finished, she took a photo and said, "Now, if you ever break my heart, I'll show this to everyone you know and everyone I know and anyone else I can."

She proceeded to place me over her lap, flip up my dress, pull down my panties, and spank my bare *** with 100 strokes from a hairbrush. Then she pulled my panties back up and told me to sit next to her. "You know, I've never kissed another girl," she said. I said, "But I'm not a girl." She looked me over and said, "You've got sexy red lips, it's close enough," and we kissed a while.

Then, her mother arrived home early. I hid in her closet for about an hour. I had to remove all the clothes on wipe off the makeup while I waited in there. Since it was just her and her mother that lived at the house, there were no men's clothing to offer to me. She handed me a towel and I walked home in that. My mom hadn't gotten home yet, so I was in the clear. To be honest, Helen and I were both qutie excited by this close call.
jorge12 jorge12 18-21, M 3 Responses Jun 19, 2011

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Hehe, sissy!

Well, that never happened, but my girlfriend continued to dress me in her clothes for a several years and still doe from time to time, but not as much anymore.

you should have remained dressed for her mother. you girlfriend would have enjoyed it more then you, not to mention her mother. she could have told her mother you were her sissy and would be so dressed at their home hence forth. Naturally you would have became their maid and would need to serve them, fix their dinner, drinks and clean the house, possibly even do their laundry. Her mother would have loved having a maid, even if it were a sissy maid. You should show this comment to your girlfriend. Everyone knows they are the stronger gender. They outlive us by 10 years on average, tolerate the pains of pregnancy which would destroy most men.