David's New Experience

It was a hot summer's day and David was taking a shower. He was alone in the house and was taking his time washing his tall, athletic body. Once the shower was complete, David dried himself off and tied the towel around his waist. He walked across the landing to his room and made his way to his cupboard. As David moved thorough his room, he heard a noise behind the door. He turned around startled. The man facing him was his mother's new boyfriend who had been living with them for about a month.

Rob was nearly as tall as David, 5'11" to David's 6'1". He was an attractive man and though he had just entered his forties, he kept himself in good shape. Rob's muscular body was very evident to David in his torso hugging black top and jeans.

"What are you doing in here?" asked David. Rob didn't reply, instead he advanced on David. David put up his hand to block Rob, but Rob simply grabbed his wrist and twisted it behind his back. Rob reinforced his position by pushing David onto his bed. The younger man tried to use his free hand to attack Rob, but Rob also grabbed this wrist and forced both arms up David's back. After some quick adjustments, David heard two clicks around his wrists and realised he had been handcuffed. David tried to kick with his legs but in a flash Rob had cuffed his right and then his left leg. Before he had a chance to speak, David felt something being put into his mouth. He tried to reject the object using his tongue, but it did not work and just made him all the more aware that a penis gag had been orally inserted. Rob removed the towel from around the waist of David, leaving him totally naked. Rob then got up and left the room, leaving David to contemplate what had just happened. He had come out of the shower and walked to his room. He had then had his wrists and ankles handcuffed and been gagged using a penis shaped object.

David's mind was racing, "What is going on, why is this happening" were the thoughts that immediately sprung up. Rob interrupted these thoughts when he returned from the room he shared with David's mother. David felt something come over his head and was then plunged into darkness. He was blindfolded. Rob lifted David over his shoulder and carried him to the master bedroom. Try as he might, David couldn't break free from his restraints, and Rob had little trouble putting a collar around his neck. Rob attached a leash to the collar and bent David over the makeup table beside the wall. The other end of the leash was then fastened to the far leg of the table, so David effectively could not move. He was aware of his naked ass on display but didn't have too much time to think about it as he heard Rob return to his legs. After some adjusting around his ankles, David felt underwear slide up his legs and into position. It felt different to his normal underwear. David felt something move underneath his body and then slipped into place between his arms and his back. He then felt the garment get progressively tighter and realised to his horror that Rob had put a corset onto him.

The younger man figured out that he was being crossdressed and his underwear was a pair of knickers. The tightening of the strings continued at pace, until David could only take shallow breaths and started to feel light headed. Even still Rob pulled on the strings; the corset went tighter than David thought possible. In his light headed state, David next felt stockings going up his legs, first his right and then his left. Rob attached the stocking to suspenders on the corset. Rob removed the cuffs from David's legs but with the handcuffs, collar and corset, David didn't have the option to run. The younger man felt footwear going on and strapped, and when Rob was finished David was on his tiptoes. With a sinking heart David knew he was now wearing high heels. Although he had never crossdressed before, it was something that had interested him and the feel of the material wrapped around his torso and between his thighs caused a reaction in David. He started to feel aroused and he could sense his swelling dick pressing against the constraints of his knickers. Rob completed the look by briefly taking off David's blindfold and affixing a wig to his head, before replacing the blindfold. David only got a brief glance around, but he noticed that Rob was completely naked and spotted his seven inch penis was semi erect.

After a pause David heard Rob return to behind him and felt a cold gel on his ass. David realised that his knickers were crotchless and exposed for Rob's every whim. Rob spread the gel over David's anal sphincter and started to gently massage the area. David could not resist the sensation and felt a strange wave of anticipation travel up and down his body. Rob rubbed his penis gently around the area and David could feel it grow as it slid around between his butt cheeks. When it was fully erect, Rob spoke for the first time, instructing David to relax. David felt anxious about the situation, he had never had experimented with anal toys, never mind anal sex. Rob gradually slid his throbbing penis into David's virgin ass. The pain that David experienced soon gave way to a new feeling of fullness. Rob continued to insert until he was fully inside David. He gently started moving in and out, the lubricating gel doing its job to allow easy motion. Rob's thrusting increased in pace and David could feel pressure on his prostate, which combined with the sensations from the bondage and the clothes made his erection even stiffer. Rob continued to pound David's ass and by this stage both men had started to grunt, David's grunting was muffled by his penis gag. The grunting and pummelling persisted until David felt a splash in his colon and he knew his anal virginity had been taken.

Rob sat down for a few minutes while both men recovered. David was still aroused and his hard on had not gone away with Rob applied some more gel to his ass. This time it was a butt plug that entered David's ass, sealing in Rob's sperm and re-stimulating David's prostate. The stimulation only increased when David heard a click and the plug started to vibrate. David felt a garment go on around his legs and up to his waist. The skirt pushed his thighs and knees together and he realised it was a hobble skirt. Rob removed David's blindfold and untied the leash from the corner of the table. After a gentle tug on the leash he got David to tiptoe over to the full body mirror. David was shocked with what he saw; his masculine body had been transformed by the corset, wig, hobble skirt and stilettos into the perfect feminine form. The anal stimulator maintained his erection and the bulge was obvious in the mirror. "Looking good" said Rob, before looking David in the eye and asking, "Are you ready for a walk downstairs?" David shook his head, he didn't know when his mother would be back and he also didn't want any of the neighbours to spot him in this predicament through the window. Rob gave another gentle tug to take him downstairs and upon David's refusal to move produced a short whip. After a few quick spanks on the ass, Rob looked again told David, "Now, are you ready to go downstairs?" David ass was smarting from the whipping, he did not want to experience that again. He stared at Rob for a minute and after Rob raised an eye brow, David gave a quick nod.

With Rob leading the way, David hobbled out of the bedroom and across the landing. The motion of walking pushed his stocking covered thighs together and he quite liked the sensation. At the top of the stairs, Rob lifted David again onto his shoulder and carried him down to the bottom. At the bottom, David was able to see out the window to his relief that neither his mother's car nor the neighbour's cars were in their driveways. None of the other residents of the street could really see into his house without coming up the lawn, so he was at least safe from voyeurs for now. Rob sat David down on the sofa and the action of sitting down only served to push the vibrating butt plug deeper into his ass. He let out a muffled grunt as Rob sat down beside him. Rob started to rub David's swollen member through the skirt and knickers and started to talk to David.

"I knew you that you would like all this."

"Is it the clothes? Do you like your silky lingerie? Does it make you feel nice and feminine? Does it feel nice on your soft skin? Do you like your silky knickers rubbing against you?

Or is it your corset and skirt? You look very feminine and sexy. I have lots more clothes for you to try. Lingerie, dresses, skirts, silky nightgowns; everything a young girl like you could want."

"Or maybe it's the feel of penises in your mouth and bottom that you like? With a real man's sperm inside you?"

"Or is it that you like being totally helpless, totally in the power of an older man as he turns you into the pretty feminine girl that you know you secretly want to be?"

David gasped as it all became too much, and his body was pushed into involuntary orgasm. His cock throbbed, and he began to ejaculate into his knickers.

"Somebody enjoyed themselves," said Rob. He gently tugged again on the leash and got David to stand up. He removed his skirt and butt plug and cleaned David up with baby wipes. He then led David into the kitchen and placed a towel on the worktop. Rob lifted David up and got him to sit on the towel. Rob moved in between David's legs and removed the gag from his mouth. He stood in that position and stared into David's eyes. David's hands were still tied and the corset still pulled on his waist, but otherwise he was free. He considered shouting, or trying to run, but instead he went over what had just happened. It had been the most erotic experience of his life and Rob was right, he had enjoyed himself. Rob had not moved from his position and David gave in to his urges. He leant forward and started to kiss Rob, gently at first and then more passionately. Both men knew that this was the start of something beautiful.