Panty Fantasies - Coleen's Magic

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A Sissy receives the ultimate night of transformation.
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He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn't _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.

Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile. The towels were Egyptian and felt wonderful. The whole penthouse suite was luxury but for the money he was paying her, it felt appropriate.

The money had almost stopped him before jumping in but after twenty years of desperate fantasies and a collection of partial experiences, he couldn't resist. She'd described things in such detail that he was completely convinced that she'd done this before. Some things had been left vague but tantalizing. Maybe it was desperation that took out the five thousand dollars but he preferred to think of it as hope.

His skin was tingling as he dried off. Her instructions had been very detailed and had taken him awhile to comply with every item. He'd cleaned himself all over and then used a special depilatory cream from his toes to his hair line. With some embarrassment, he'd given himself an enema. He'd never felt so clean and his skin so smooth.

Leaning close to the ornate mirror, he took a good look at himself: fit, toned, a little on the lean side, a little shorter than average, longish black hair that he kept combed back loosely. He'd never been unhappy about his build. The fact that he could dress off the rack at women's stores made his secret life ever that much richer. Most guys were too big, too tall, or just shaped too masculine. Maybe the genes of his mother had given him a just little extra curve here and there. It had been embarrassing as a kid but when his secret fantasy life had blossomed he'd cherished any little thing that made him feel more feminine.

Once he was dry he stepped back. It took him a minute to recognize himself. Gone was the moustache he'd had for the last decade and there wasn't even a hint of five o'clock shadow. He definitely looked younger and, if he wasn't just delusional, more... if not feminine, well, at least androgynous, less obviously masculine. He found himself daydreaming.

It had taken shockingly little time to set the whole thing up. He wasn't deluded that his particular fantasies were "mainstream" so he was pleased that Coleen had understood his descriptions so quickly and well. She'd added suggestions that had given his hard-on an almost painful rigidity in excitement. She'd spoken of applying her talents in very similar situations with other friends. She never spoke of clients or customers. Everyone was a friend which he felt was a nice touch.

He'd only discovered her after an awkward first visit to a swinger's club where he'd been too scared to join in the fun. He just couldn't get my courage up to strip down to his favorite lingerie in front of strangers though he had masturbated three times in the men's room.

Maybe it was his reluctance that caught Coleen's eye, but just before he was about to give up and head home, she asked to sit with him. She later admitted that she recognized his panty lines first and then the tell-tale bumps of his garter belt. For a long time he'd thought she was a run of the mill prostitute, even in a swinger's club. But she had such a warm and easy way about her that he found himself telling her some of his secrets. They'd exchanged emails. A follow-up dinner at a secluded restaurant brought the rest of his secrets to light and she revealed that she was a 'fantasy maker'. While their arrangement would have to remain a secret from any legal authority she claimed that she was not a hooker. Somehow her veiled anecdotes of previous experiences seemed more than just trying to sell him on the proposal. He admitted he could have been completely deluded but he felt they had a real connection. The rest had come together in a matter of days.

Glancing at the time, he only had a few minutes left. The experience he'd arranged was not one of submission to a cruel dominatrix. Nothing killed his desire and his erotic mind-state more than someone trying to hurt him or cruelty. No, Coleen would be in charge but sensuously and kindly. At least that was what had been arranged. Still he wanted to comply with her directions in every last detail to make sure nothing would upset the experience.

He walked out of the bathroom and on to the warm, soft carpet. Looking out through the breath-taking large penthouse windows he saw Chicago arrayed out beneath him in the setting sunlight. The Sutton Place Hotel had been an excellent choice and he loved her taste.

The robe slipped over his arms and shoulders like a caress. It was a women's satin robe that fit him perfectly and he started to get erect. The satin just felt so amazingly wonderful on his tingling skin that a moan escaped him. From his toes to his nose, his skin seemed so sensitive that even the light brush of the satin was thrilling. His skin definitely felt different but he loved it. The fleeting thought of masturbating caught his attention but Coleen had been very explicit about him not masturbating for two weeks up to their encounter.

The chunk of the suite's door's lock opening made him freeze. The door swung open and she came in. Her perfectly straight red hair flowed past her shoulders. Her emerald green satin blouse was modestly buttoned but was still cut tight enough to showcase the curves of her large breasts. Her hips and legs were accentuated by a pair of tight jeans that looked like they'd been sprayed on. High stiletto heels clicked on the tile of the suite's foyer until she reached the carpet. The door drifted shut and locked behind her.

"James!" she smiled as she walked up to give him a warm hug. He hugged her back and shuddered as he felt her body against his own and the robe shifted on him deliciously. She gave him a kiss on his lips, not quick and chaste, but also not overly lingering. "I'm so glad you could make it. We're going to have so much fun."

Her enthusiasm was a wave of energy over him and he couldn't stop smiling himself. He watched her put her purse, the room key card, and plastic shopping bags on a side table, taking the quick opportunity to enjoy the view of her bottom, her curves, and that fluidly shifting hair. The bags were clearly from Victoria's Secret, Frederick's of Hollywood, and Cupid's Boutique.

"Were the instructions clear enough?"

"Very clear and finished completely."

"Great! We can jump right in. Now remember we don't have to rush anything. This isn't a sprint. We've got the suite all night. Also, it isn't a marathon. When you're sated and tired, we can stop for the night. We'll see how it goes. We might be able to catch a little sleep together later."

Just sleeping with her sounded wonderful to him.

"As we discussed, I do have some techniques that are rarely used by others but I think really elevate the experience to something you've never reached before. If you think back to the first time you touched panties and wanted to put them on... the first time you slipped your sister Sarah's panties on you... the first time you braved Victoria's Secret to buy a teddy for yourself... That first time intensity is what we'll be experiencing tonight."

He nodded, not trusting his voice with his nervous excitement. His cock was rock hard and he hoped it wasn't leaking against the satin robe. She read his mind and glanced down.

"I think you're happy to see me," she gushed and that line between a purchased experience and sleeping with a lover was blurred in his mind again. He'd been to Vegas a few times to try and have his fetish indulged. The experiences had been enjoyable but there had always been a clinical side to it all, an emotional detachment. He felt none of that with Coleen. In fact, most of their dinner together had been talking about things besides sex. He'd really enjoyed her company.

She reached into her purse and pulled out a foil pouch. He recognized it as a condom. He gave her his hand as she got down on her knees, giving him a disarming giggle while she did so. She divided the front of the robe to reveal his smooth, hairless cock beaded with precum on the tip. She reached out one red-nailed finger to catch the bead on her tip and then lifted it to his mouth. He opened and let her rub the precum softly on his tongue. She winked and returned to her knees.

"Such a beautiful cock, James," she said softly, staring at it as her hands tore open the condom packet. "You must really please the ladies, so long and thick." Her words were like honey and he grinned at her praise.

"Here's a little trick I learned that I think you'll like," she continued. She took the condom out of the packet and placed it in her mouth. After a moment of moving it around behind her lips, she opened her mouth and began to take his cock in between her lips.

He groaned in pleasure as he felt her teeth and tongue gently pulling the latex condom on his cock, stretching and unrolling it down his shaft as his cock disappeared in her mouth. He closed his eyes and absorbed the sensations of her heat and wetness, her eager tongue. She was massaging his cock head with her tongue as her teeth unrolled the condom. His tingling skin made the pleasures even more intense. Looking down at her, her beauty, his cock disappearing into her mouth, he gulped and felt his orgasm rushing up on him.

"Wait, I..." he blurted but she continued getting the condom unrolled 3/4 way down his shaft when she couldn't take any more of him in her mouth. His balls clenched, sending his brain a blast of sexual joy and then throbbed and flexed, pumping out his cum. "Oh god yes..."

Coleen's hands gently grasped his thighs and she kept him fully in her mouth as he came, moaning softly as she enjoyed the feel of his throbbing cock and the flowing cum. When his wave finally subsided, she helped steady him as he felt momentarily weak in the knees.

"I'm so sorry, I..." he began as she pulled her mouth off his cock.

"No, don't worry, honey," she cooed. "I'm pretty flattered actually. I've never had a lover come so quick in my mouth." The condom was still firmly on his cock and the end was drooping and heavy with his seed. She cupped the end, feeling the amount and heat of it. "That's a lot of cum... we're lucky."

She carefully slid the condom off his cock, keeping the reservoir filled with cum carefully protected. He watched as she walked to the suite's kitchenette and got a glass. She poured the come into the glass, working the condom to get out every last drop. After fetching a fresh packet, she returned to him.

This time she slid his cock in her mouth without the condom and quickly cleaned it of lingering cum. His erection renewed quickly. She let it come out with a pop and licked her lips. "I might just have to steal some of that later," she teased before wiping off the remaining wetness and rolling down the new condom with her fingers.

"Come with me," she said with a purr. He followed her into the bedroom of the suite where he sat on the edge of the bed. The pink satin comforter felt wonderful against his bottom and legs.

Coleen brought a chair over and placed it facing him. She sat down and looked at him. Several moments went by as their eyes were locked before she spoke.

"Look at my breasts..." She slowly undid the buttons of her satin blouse, the green material slipping open further and further to reveal her large breasts held in the sheer black lace cups of her bustier which did little to hide her nipples and their hardness. The black satin bustier hugged her body tightly. Sliding the shoulder straps of the bustier off her shoulders gave her enough play in the material to slowly work the lace cups down. Her beautiful breasts became fully revealed, round and firm.

Taking one hand, she gently touched her left breast, cupping and squeezing it. He could see her nipple stiffen further. "Do you like my breasts?"

"Very much!" he blurted and he could feel how hard he'd become.

She began to run one finger very slowly around her breast, in a circle around and around her nipple.

"Watch my finger... Each time it goes around, you'll feel more relaxed, more comfortable with whom you want to be." The finger circled again slowly. "Relaxed and natural... relaxed."

He opened his eyes after an odd blink to see her still circling her breast but from her face he could swear she'd just cum. Her free hand slipping out of her unbuttoned jeans added to that conclusion. He could glimpse black satin panties in the little gap in the top of the jeans.

After a few moments, she stood and put the chair back. She waved him to standing as well. "Take off your robe, sweetie." He slid the satin from his shoulders and let it slide fluidly down his body to a heap around his feet. Even the current of air of its passing felt wonderful on his skin.

Coleen walked to the other room and came back with the Cupid's Boutique bag. Leaving it on the chair, she pulled out a pink satin blindfold and stepped behind him to place it on him. She pressed into his body as she reached around to adjust it on his face, her breasts making him shudder with pleasure as they pushed against him.

Once the blindfold was secure he could see nothing but a very dim grayness. She didn't leave but slid her arms under his and around to hug his chest. Now he could feel the undone snap of her jeans against his ass too.

"Breasts are womanhood," she began softly, talking into his ear. Her hands moved to his pecs and began to stroke him. They massaged his skin and he felt it all tingling. "Full of life they are very sexual. Full, round, supple breasts are beautiful, entrancing men and women alike with the desire to kiss, lick, and suckle them."

His chest was really tingling now and he felt her fingers pulling at his skin. Something was happening.

"Oh the pleasure they bring a woman... so sensitive and sensual... making her clit tingle when they are brushed and throb when they are worshipped..."

"Feel my full breasts against you; imagine how they would feel to have, their weight, their size transforming your figure into a gorgeous woman..." She was pulling more now and he felt a weight on his chest. "Beautiful breasts inside delicate bras or bikini tops, always threatening to escape and be free, to be seen and admired, to be lusted for..."

He sighed as a wave of pleasure washed over him and he realized that she was cupping and massaging his full breasts. Blinded by the satin over his eyes, he could only strain to interpret the sensations, the way she would move them, lifting them and stroking them, the tingle he'd feel in his toes and balls when she brushed his full nipples. He'd never felt these sensations before and he felt transformed.

"Oh god yes," he breathed and she let his hands replace hers. He felt them, warm and real flesh, truly transformed to have the young, full breasts he'd always fantasized about. She stepped away and came back after a few minutes.

"Good girls wear pretty bras on their breasts," she said softly, slipping the material around his waist and then pulling it slowly upward, letting the satin cups, the underwire, and the elastic straps all play against his skin. She guided his arms through the shoulder straps and then brought it up. His breasts strained the cups as she fastened the back hooks but he thought the tightness felt divine. He'd worn all manner of bras and lingerie wishing he knew what they truly felt like full with breasts and now he was experiencing every bit of it.

His cock was throbbing with his heart beat and he knew that he was more than ready for another orgasm. He realized that the cream Coleen had made him shower with had so heightened his sexy smooth skin's sensitivity that every brush of her skin or pretty lingerie was amazing. It was a thousand nights' fantasies come true.

Coleen loosened and removed the blindfold, letting him look down at his breasts in the pink satin bra. He continued to cup and stroke them happily.

"Oh my!" exclaimed Coleen gently. "You have no panties! Girls without their panties are just little cock-sluts, aren't they?" His mouth gaped but just before he recovered to say something she continued, "We'd better get you a pair."

He nodded although it was a bit half-hearted. He wanted the panties but being a little cock-slut sounds pretty good to him too. She fished a pair of pink satin string bikini panties out of the Victoria's Secret bag. He noticed they had the same black threaded ornamental stitching that he saw on the bra itself.

She knelt behind him and nudged him to turn a little so he could see himself in the full mirror. His hands were still cupping and feeling his breasts as he let her lead his feet into the panties. Then her hands pulled them slowly up his legs, letting the satin, the ruched elastic waist, the soft cotton gusset stroke his skin. He was trembling with pleasure as the panties reached his upper thighs.

"There is nothing," she began as she started to pull the material into place. "like the feel of satin panties, tight on a girl's bottom..." The waist pulled up and he felt the satin slide up and then taut over his own bottom. "And delicately over her pussy..." Her fingers brushed his asshole through the satin, tucking a little material between his cheeks.

She left the material bunched under his cock. There was no way it would nestle inside at its current state of raging erection. He owned plenty of roomier pairs of panties at home but they always fit him like a bag. He didn't want to give up how perfectly these panties seemed to fit him, touching his skin the right way in every place.

Moving around to his side, she pulled another pair of matching panties out and lifted them over his cock. He watched everything in the mirror as this beautiful woman draped the panties over his condom-wrapped penis and then began to stroke him with her hand.

"Pretty girl wanna cum in my panties?" she asked him. On top of the sensations racing through his body, those words blew his control.

"Oh god yes yes yes," he blurted as his balls clenched fiercely, electrifying his body with pleasure and then throbbed with powerful contractions and even more cum shot into the condom. He had to sit on the edge of the bed before the orgasm began to subside as his legs had gone silly on him.

"Mmmm, good girl," mused Coleen as she stroked all of the come out of his cock into the condom. She tossed the panties on the bed and teased the hanging bulge of come in the condom with her tongue as she looked up at him. One final ejaculation boiled up at the sight of that, pouring out, and then he was spent.

She quickly handled the condom and cleaned him with her tongue. Finally, his body was relaxing and his cock got soft. She deftly pulled the panties in place and smoothed the front of them with her hand. She kept pulling them a little this way, a little that way, tugging on the waist band, until she asked him to stand again.

"Do you like your panties?" she asked. He stood and looked in the mirror. He was stunned. He was looking at a beautiful woman with full breasts and panties smooth over her pussy. He saw no bulge in the panties at all and they looked perfect.

Coleen stepped behind him and tugged in the waistband a little on either hip until the satin was perfectly smooth between his legs. "You look good enough to eat..." she whispered.

He had to sit on the bed. As soon as he sat he had to lie down. His head was spinning in amazement and a rush of arousal. When he looked up, Coleen was slipping out of her blouse and heels and peeling down her jeans. She was left in a black satin bustier and matching satin thong panty.