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From confessionsinpantyhose.com

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.

Since he received quite a chunk of change for Christmas, he thought he might as well go all out and spend it on the good stuff. You know, higher priced pantyhose instead of the five-dollar pairs he typically purchased at a drug store, and decent lingerie that would fit him like it should for a proper woman-to-be.

Rob excitedly drove to the mall, parked and walked into the Neiman Marcus nervous as hell. Since it was the day after Christmas, however, the store was jammed packed with shoppers going mad everywhere. Rob figured the hoard of people would be the best cover for him browsing the lingerie section without attracting attention. This eased his nerves somewhat.

He first stumbled upon the array of Wolford pantyhose in front of him. He had seen countless images online of women wearing those Wolford Neon 40 with that gorgeous shine that he had to get them. In fact, he picked out two pairs, one in a suntan colored Gobi and the other in black. Holding the pairs in his hands was even enough to give him an instant erection.

Next, Rob  found himself in the middle of the lingerie section looking stealthily at the bras and panties surrounding him. There were almost too many to choose from but he glanced upon the Wonderbra push up bras which he thought would be perfect for his “flat chest.” Indeed it was as he picked out a black bra in his size and a pair of black thong panties and boy short panties in a size just larger than his mother’s.

Nervous again, Rob made his way to the line at the cashier. The ten minute wait to check out nearly killed him yet the thought of himself basking in his new silky Wolford pantyhose and sexy lingerie was enough to allow him to keep his nerve during his purchase. Before he knew it, he paid and was out the door with his bag of goodies and driving home.

Since his mother was still at work, when Rob arrived home he immediately emptied his bag, stripped off his clothes and went to work trying on his new lingerie, all for his own self. First, he slid the pair of suntan Wolford pantyhose over his legs. Then came the black thong panties and, finally, he strapped the black Wonderbra around his chest and shoulders. He then made a quick dash to the huge mirror in his mother’s room.

What a sight it was in front of him. His long slender legs covered in a brightly tanned glow. The thong panties draped over his pantyhose but not quite hiding the bulge emerging from his crotch. Then there was that beautiful bra fitting so perfectly and giving him a bit of a womanly bust.

Rob felt so sexy and feminine staring in the mirror that he began to tremble from the sensuality of it all. A moment so intense that he would remember it for the rest of his days as a crossdresser. In the meantime, though, he felt he needed to complete the “look” as he noticed his mother’s makeup sitting there just below the mirror.

So he grabbed the red lipstick, made a pucker with his lips and put it on like he’d seen his mother do a thousand times before. Rob set the lipstick down and watched himself joyously pucker and kiss in front of the mirror. Little did he know that someone else was watching the show from behind.

“Rob, what are you doing?” exclaimed Wanda, Rob’s mother.

In complete surprise that his mother came home early, and somehow not hearing her come in the door, Rob grabbed a t-shirt lying on the floor in a vain attempt to cover himself (or at least his erection) before facing his mom. The overwhelming feeling of being a woman suddenly turned into complete horror as he turned around to see his mother slack-jawed at the sight of her own son in lingerie and pantyhose.

Then there was the shock Wanda had of her own which turned to a sudden anger thinking that Rob was stealing and wearing her underwear. After realizing, however, that none of what Rob was wearing was her own, her anger quickly switched to confusion. Why was her son wearing lingerie that was much nicer and more expensive than her own?

“Where did you get that lingerie?” she asked.

“I bought it,” Rob said rather shyly.

Yet in Wanda’s rather backward thought process, and completely oblivious to the concept of crossdressing, she realized that Rob must be gay and is trying to compete with his own mother for men. Thinking she would have to set him “straight” again, she quickly devised a plan in her head to do so.

“So you steal my makeup and want to look like a real woman then?” Wanda asked with another question.

“Well yes,” Rob responded, still in shock and embarrassment.

“Then either I take your car away or this is what we’re going to do…” Wanda replied.

Wanda then set out with the first part of her plan which was giving Rob the option of having his car taken away or going out on a “ladies” night with his mother. Oh, little did Rob know that the plan she had in store for the night with her feminized son was suppose to “cure” him.


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.

Rob, not in a position to argue with his mother, reluctantly agreed. On to get dressed up they went.

“Let me see…,” said Wanda thumbing through the dresses in her closet. Actually, since Wanda was divorced and single, her selection of attire consisted more of the type to get a man’s attention, just what she hoped for Rob. She at last found a tight red spandex mini-dress she thought perfect for making her son appear very noticeably as a womanly.

“Put this on,” she says to Rob, with a grin, who is still in his lingerie and pantyhose.

Rob had never before thought to try on his mother’s “fancy” dresses since he really only began to experiment with trying on lingerie, apart from just his usual fantasies in pantyhose. Yet, as he slipped the tight red mini-dress over his pantyhose, then his bra and over his shoulders, he couldn’t help but to feel his earlier feminine fantasy, while solo, starting to come back to him again.

He found it rather odd given the circumstances, yet he went along with his mother’s order without uttering a word.

Wanda continued the transformation of her own son finding and placing an old, but still attractive, wig to his head. Then she grabbed some matching red high heeled open-toe sandals that just barely fit Rob but nicely highlighted the toes of his Wolford pantyhose. After, she removed his earlier smudged lipstick application and meticulously repainted his face to complete the look of an actually very convincing teenage girl.

After all, Wanda wanted every guy within view hitting on her son. Aside from public embarrassment, having to fend off dirtbags, that routinely harass her on a daily basis, would teach him another lesson. This, unfortunately, was just another one of her ancient remedies from the days of washing out your mouth for saying a bad word.

Little did she know she had a crossdresser in the making standing right before her as Rob stood in front the large mirror yet again admiring his now very womanly self. The curves in his dress helped by the Wonderbra, the black high heels highlighting his long pantyhosed legs. And there was that perfectly applied makeup by mom that made him convinced for the first time that he could pass for a girl.

As quickly as Rob started to fall in love with himself, he realized the other part of the bargain with his mother: having to go out with her, in public view. This put him in a state of panic. What will people think of him? Will he run into any friends or people he knows? Will he be made fun of for the rest of his life?

Oh the sheer horror!

Wanda got dressed herself in a more conservative look, that is, a similar tight dress in black and with a hem line slightly lower than Rob’s. She “borrowed” and ripped open Rob’s other pair of black Wolfords (without asking) and quickly slipped them over her legs (obviously an attempt to not allow Rob to outdo her with his sexy legs) . Then she found some black high heeled stilettos to complete her own look.

“Time to go,” she says to Rob as he reluctantly followed her out the door, still without saying a word and the fear of being “discovered” dreadfully occupying his head. They then drove down to the first stop in Wanda’s “plan:” her local dive bar, The Horseshoe. They arrived and made their way in, Rob trailing behind.

It was crowded in the bar at the time as Wanda, with Rob nervously in hand, wandered among the crowd of people who all knew her but were wondering who the attractive young woman was with her.

“Oh, this is my son Rob. He wants to play dress up today,” Wanda said loudly making sure as many people heard as possible. This paralyzed Rob into complete silence, putting him into an embarrassment that far outdid his mother catching him in her bedroom a bit earlier.

Yet the reaction of Wanda’s acquaintances was unexpectedly, at least to Wanda, of curiosity rather than disgust. This beautiful girl is actually her son? He must be practicing to be some kind of actor or something. Why else would a mother take his son out to a bar completely dressed as a woman who arguably looks far better?

Unbeknownst to Wanda, intentionally trying to humiliate her son, Rob took notice of the curious vibe of the people surrounding him which quickly eliminated his fear. He then gathered the best girl voice he could muster and confidently said hello in a rather high pitched tone to everyone around him.

Rob, however, didn’t realize his mother had just left him alone to talk to another friend at the bar, also intentional on her part. Or in other words, another part of her plan for the evening: let her son fend for himself, in a bar and in drag (that ought to teach him).

He was too busy, though, chatting with a rather young attractive woman he had just met who was curious about his transformation to a woman. Strangely, not curious as to why but how he was able to do this and look so spectacular. Rob cooly played to her curiosity by saying it was a social experiment for a psychology class. He then goes on about his each article of clothing he is wearing, from the Wolford pantyhose to the Wonderbra.

Rob seemed to have girl chat nailed down rather quickly. Not bad for a guy.

Then, suddenly, this young woman, Renee, cuts off Rob at mid-sentence, grabs his hand and heads for the bathroom. The women’s bathroom. Rob excitedly follows her inside without even a second thought. To him, it’s as if he was given a pass inside an exclusive club full of women, albeit ones that just needed to urinate.

Renee didn’t waste time in pulling Rob into a stall then grabbing his head into a passionate kiss with one hand. The other hand reached down to pull up his red dress at the waist and caress the pantyhose covering his ass. She couldn’t help but to grab it after.

“Your tights look so hot on you,” Renee says taking a moment away from the passionate kissing but returning to it again. Her hand then switched from his ass to caressing his instant hard-on jutting out from the front of his Wolfords. Rob, savoring the moment and still in the passionate kiss, reaches down for the pantyhose covering Renee’s ass and grabs it, with the silky feel making him even harder.

Renee suddenly stops kissing Rob, drops to her knees in front of him and, instead of pulling his pantyhose down, begins to slowly lick his joy rod but right through the Wolfords covering it.

Rob couldn’t believe what was happening to him as he started to moan lightly… in his girlish voice.

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.

Rob, still in the afterglow of his first hummer and at a loss for words, replied, “Um, well… sure.”

Renee gave a quick kiss to Rob, giving him some of her still-come-soaked tongue, then unlocked the bathroom stall, quickly straightened her hair, wiped her face clean and calmly walked out of the ladies room. Rob then soon followed suit, adjusting his now-wet pantyhose and red mini-dress. His makeup was even noticeably smudged yet he didn’t care, showing a huge smile he couldn’t help but to have on his face.

His mother Wanda got up from her seat at the bar and went up to Rob after seeing him walk out of the ladies room.

“Where have you been and… why are you smiling like that?” she asked in a rather worried tone.

Wanda, as old-fashioned as she was, was completely oblivious to the obvious signs of what transpired earlier in the women’s bathroom. Instead she became concerned that her son might actually be enjoying himself dressed as a young woman, and a sexy one on top of that. This was definitely not a part of her plan to teach her “supposedly gay” son a lesson to never crossdress (whatever that was) again. Or be gay either.

“Time to take Rob to a real place which should really embarrass him,” Wanda thought to herself as she grabbed his hand and made her way out of The Horseshoe. Rather angry at her faltering plan (but trying to hide it), she then told Rob her next “plans” for the evening.

“Now we’re going to really have some fun my dear,” she said to Rob, smiling, as she first fixed the smudged makeup on his face. Then they got back into the car and drove off.

Wanda thought the next stop, Mix Club, would do the trick. It was always full of younger people, as she would know, since she had usually frequented it being the “cougar” that she was. Rob would be hounded by so many younger college-aged guys that he will leave the place in tears begging his mother to take him home.

“Yes, that ought to set him ‘straight’ this time,” she thought as she was driving.

That’s we she thought at least.

They soon arrived at Mix Club, rather early in the evening, but with a lot people inside. A lot of young men, that is, which eased Wanda a bit knowing that her son would have to put up with the sausage fest inside being the only “girl.” That left Rob being the pretty young crossdressed girl with his pick of the guys. The thought of this made Wanda laugh to herself.

Meanwhile Rob was petrified at the thought of stepping inside. Although he could say he had a successful outing at the last bar, he had another girl he could at least (ahem) talk to. He wasn’t too sure if his crossdressing for a psychology project story would fly with the numerous amount of guys inside.

Wanda, yet again, grabbed her son by the hand and made her way inside. Immediately she spotted an old “acquaintance,” a college student she had met at that same club weeks ago. She left Rob behind to fend for himself knowing full well that, this time, he wouldn’t leave with a smile this time around.

Rob’s earlier confidence at The Horseshoe started to wane. He could hear those whispers as he walked through the club and among the younger men.

“Is that a dude?”

“I don’t know but I’d do that.”

Then Rob walked up to his only sanctuary, which had served him well in the last bar: the women’s bathroom. He walked in, no one around, entered a stall and locked the door, too afraid to come out. Yet, while sitting on top of the toilet, he couldn’t help but to recall the excitement of Renee sucking and slurping on his pantyhose covered penis a short time earlier.

In fact this made him so horny again as he lifted up his mini-dress revealing the pantyhose and lingerie he had bought earlier in the day. He then massaged his member over the pantyhose making it rock hard again and sticking out of the shiny nylon like a tent. He then began to wank it, hard, pretending Renee’s lips were all over it again. He rubbed his legs together enjoying the silky feel of his pantyhose, heightening his pleasure even more.

His fear of the masculine world that was just outside was momentarily replaced with his self-erotic joy. Yet just a few strokes into his masturbation, someone walked into the bathroom. Rob suddenly stopped his jerking off and remained quiet ripping off a piece of toilet paper to disguise what he was really up to.

“Excuse me,” said the voice, feminine but somewhat deep, from outside of the stall.

“Yes?” responded Rob, slightly delayed in getting his girly voice back together.

“Hi, I noticed your outfit as you were walking by.”

“I just love that dress and tights.”

“They look so sexy on you!”

Rob was rather shocked but flattered by what he had just heard. All of sudden his confidence came back as he flushed the toilet and pulled down his dress trying intently to cover up his hard-on. He unlocked and walked out of the stall to the site of an amazing beauty before him… another woman in a similar dress, but in black, and with what also seemed to be black Wolford pantyhose to go along with it.

“Hi, I’m sorry to bother you but I just had to say hi,” said the young woman. Yet Rob noticed something odd about her. “That voice, it sounds rather manly, but she can’t be…” he thought, “but she looks so sexy.” The next thing he heard, however, confirmed his suspicion.

“I also like to play dress up to too hun.”

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.

Sandy, not surprisingly, was completely sympathetic to Rob’s tale of what went on that day. She was even more impressed, however, by how he looked in that red mini-dress and how feminine he carried himself, being his first time “out” as a crossdresser. Of course, she couldn’t help but to be flattered at the fact that they were both wearing the same pair of black Wolford Neon pantyhose as well.

They both continued to chat on and on in the ladies restroom as they hit it off like two best friends. Really, nothing different than two girls discussing their favorite clothes and makeup. Sandy even left the restroom quickly to return with a gin and tonic for Rob so they could share a drink together.

As their conversation ended, Sandy gave Rob a kiss on the cheek leaving a lipstick print. “I hope to see you again soon,” she said, with a wink, and leaving the restroom. Rob was absolutely floored during his girl chat with Sandy, in fact, so much that he noticed he had an attraction to her.

“Could this feeling be real?” he wondered as he stared into the mirror looking at his red dress and beautifully made up face with the lip print on his cheek. He even wondered for a second if this made him gay yet the gin and tonic he just drank made it not matter even the slightest bit.

Out he finally went from the ladies restroom when he noticed, a short distance away, his mother making out with some random guy. “That’s my mom,” he thought sarcastically as he suddenly conjured up an idea of his own. Then, in an instant, he went to carry out his plan.

Noticing Wanda’s purse on the table right next to her, and with his mother obviously occupied, he strutted over and grabbed the car keys from inside of it. Next, he searched for Sandy, who was waiting at the bar ordering another drink, found her and tapped her on the shoulder.

“Wanna go for a drive?” Rob asked her.

“Anytime sweetie,” Sandy replied ordering two drinks that they would later sneak out of the club with.

Then out of the club and into Wanda’s car they went, giggling like the two convincing girls they were while slurping down their gin and tonics. As Rob started driving, Sandy began directing him to a hill just outside of town where no one for sure would be at this late at night.

An excitement filled Rob as he began to pass his hand over the pantyhose covering Sandy’s slim thighs. This was all new to him since he had never before been attracted to another male, albeit a very beautiful female crossdresser. He didn’t care at the moment, though, with the second gin and tonic he had helping that out.

Sandy, visibly flattered, gave rob a soft rub over his silken thighs and onto his package, emerging tightly out of his panties and pantyhose underneath. Then she grabbed his hand and locked it with her own like boyfriend and girlfriend or, really, girlfriend and girlfriend.

They arrived to the hill overlooking the city and, not a moment too soon, they immediately began to makeout, grabbing the pantyhose covering each other’s ass and enjoying the silky feel against one another. They both then became aroused enough to where Sandy had to finally ask the question.

“Have you ever been with another crossdresser?” to which Rob shyly replied, “No.”

“Don’t worry dear. We’ll go gentle,” said Sandy as she gently caressed his ass while lifting up his mini-dress to reveal the black shiny Wolfords. She then pulled down his pantyhose, then the black thong panties he had on underneath to reveal his naked ass. At last, she slipped on a lubed condom over her massive erection.

Rob was initially terrified at what he was about to experience which only intensified as Sandy began to penetrate him. His ass was being violated ever so slowly but leaving a pain he had never felt before, ever. Sandy, however, was aware of the virgin ass that was before her and the pain he was probably feeling so she didn’t rush entering into Rob.

But then the pain Rob felt started subsiding as Sandy finally penetrated as far as she could. Then another slow second stroke and a third until finally she was ramming him repeatedly, clapping on his ass, which Rob now began to enjoy as he moaned and screamed louder in his girly voice.

Sandy kept at her frantic thrusts until she finally came with a high pitched “Ahhh” in relief. At that moment Rob finally felt like he was a true woman, oddly enough, just like his mother. The feeling that he was just fucked made him feel like a cheap whore, yet was so intoxicating as it truly felt more feminine than he could ever dream of.

Then it was Rob’s turn to make the slut out of Sandy as he now pulled down her black Wolfords and slipped a condom over his own raging member. Rob, however, didn’t have to ease into Sandy’s experienced ass with care as she gave him the order to go “fast and hard” to which he happily obliged. His member easily penetrated her loose ass and he was clapping against it just as she did to him.

As typical for teenage boys, it took less than 30 seconds for him to come yet Sandy still enjoyed every last second being pounded by the much younger teenager.

Both Rob and Sandy began to kiss and pet each other in their afterglow while tossing out their used condoms and straightening out their dresses, pantyhose and lingerie underneath. Sandy even helped Rob to clean off his smudged makeup and reapply it while doing her own, making themselves ready to go back into the public again.

And off they drove back into town, playfully stroking each other’s nyloned legs as before, heading back to the Mix Club they were at earlier. Rob began to wonder what his mother’s reaction would be this time since he snuck off with her car while leaving her at the club.

“God, I hope she punishes me again,” he thought to himself with a huge smile.


From psychcentral.com

As far as I can remember I have been easily aroused by women wearing pantyhose. At the age of about 14 or 15 i started wearing pantyhose and masturbating with them. At the time i was ashamed to tell my girlfriend at the time about it. I continued this up until about 19 or 20, when i finally had a girlfriend who i told about my fetish. i thought that by sharing this with my significant other at the time that it would help but it did not. i would just want it more and more.

now I am in a long term relationship with a woman that i love . I have told her about my fetish and how i masturbate with her pantyhose and she said that she did not have a problem with it. She wears pantyhose for me rather frequently because she knows that i really like them. Even still i have cheated on her with a ex-girlfriend just because I wanted to see how a certain type of pantyhose on my ex would look. we did not have vagina sex ,but we did engage in sexual acts.

i feel bad for two reasons : 1. is that i cheated and 2. the ex girlfriend that i had my pantyhose encounter with i really don’t want to have anything to do with her but just with my fetish.

My obsession has really intensified to the point that i am doing more to achieve a stronger orgasm. Recently I had started to look for more ways to achieve a bigger orgasm, which has left me morally conflicted. I really feel like my fetish is out of control. In general my fetish for pantyhose has lead me to do immoral things that i would not do unless pantyhose are involved. i need help and want advice on how should i tackle this.


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