Tag: teenage crossdressing

Part 3: “Hard” Lessons Learned

Part 2: All Dolled Up

Part 1: Fantasy Gone Horribly Wrong

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Part 4: Punished, And Liking It

Rob was shocked by what he heard. There in front of him was what appeared to be the only other female in the club (besides his own mother) yet was another crossdresser, just like him, who was dressed just as sexy but in a black dress and also wearing black Wolford pantyhose, just like he was. “She,” however, appeared to be several years  older, much like the other college aged dudes in the club.

“Oh, well nice to meet you,” said Rob, “I really love that dress and are those Wolfords you have on?” he continued admiring the confident beauty in front of him.

“Thank you darling, I wouldn’t wear anything else just like you,” replied Sandy, the other crossdresser. “What brings you here?” she then asks.

Rob decided enough with the whole psychology project excuse and explained to Sandy the whole story right from the top. First the trip to the mall to buy sexy lingerie and pantyhose, then racing home to try them on, next getting caught by his mother and, finally, being “punished” by going out to a bar and club with his mother as his teenage crossdresser self.

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Part 2: All Dolled Up

Part 1: Fantasy Gone Horribly Wrong

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Part 3: “Hard” Lessons Learned

Renee continued to eagerly suck on Rob’s member, or should we say blowing the Wolford pantyhose encasing it. Since it was his first blowjob, yet alone while transformed into a very sexy girl by his mother, he didn’t know what to do or what to expect, normal for a teenager. Yet he really didn’t have to as his erection did all the talking that was necessary.

Then came the point of climax a short while later as Renee kept to her task, not missing a slurp over the silky nylon covering his rod. “Ahhhhh,” Rob let out as he came with a pool of hot sticky love juice squirting out through his newly bought Wolfords. Renee was kind enough to lick it all off hungrily not wanting him to “stain” his pantyhose on his one night out as a woman.

“Did you like that?” Renee asked.

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Part 1: Fantasy Gone Horribly Wrong

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Part 2: All Dolled Up

Rob was still in deep embarrassment of having his mother walk in on what was the probably most exciting woman-to-be fantasy he had acted out yet. There he stood in with his new Wolford pantyhose gleaming over his legs, a Wonderbra fitting so perfectly giving his chest a womanly appeal and, let’s not forget, thong panties to match.

Then there was that red lipstick painted neatly over his lips as prime evidence he “borrowed” it from his mother. He knew he was at the mercy of whatever his mother’s reaction was but, when he heard her say she would take his car away, his thought quickly turned to losing his prized Christmas gift.

“We’re going to go out on a night in the town, you and me, and since you want to dress like me then you’ll go out that way too,” continued Wanda. Shaming him in public ought to teach him a lesson and will ultimately set him “straight” again, she thought to herself.

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Part 1: Fantasy Gone Horribly Wrong

It was the day after Christmas when Rob, who just got his drivers license and a junker of a car as a gift, decided to drive downtown to the shopping mall for a little specialty shopping with the money he received, also as a gift. You could say he was shopping for clothes like all the other teenagers with Christmas money to burn, except Rob had something a little different in mind.

You see, for several years Rob has had a fascination with pantyhose. At first it was just a simple curiosity trying on a pair found wadded up on the floor of his mother’s room. The silky feeling and shiny appearance on his legs, however, was enough to make it a habit of his “modeling” pantyhose on a regular basis. As an only child of a single working mom, he had plenty of opportunity to develop his fetish.

Yet as Rob had grown more fond to the feminine sensuality from wearing pantyhose, he began to experiment more with his own crossdressing having grown a curiosity for trying on more feminine things. Starting out with his mother’s lingerie, he slipped on her bras and panties along with his usual pantyhose. This, of course, made him incredibly horny even though the lingerie was a bit ill fitting for him. He wanted his own lingerie to wear.

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