*Since I forgot to put tags in the title, this story includes: cross dressing, feminization, femdom, cuckolding, oral, bisexual play and humiliation. Thanks for reading!*
“Come on out! It’ll be fine!”
Kevin took a deep breath. He and Sandra had been friends for years and it wasn’t as though he didn’t trust her. Still, there was a difference between trusting a friend and taking a step that he, himself, wasn’t sure he was ready for.
His chest was a little tight and that made it difficult to breathe. Only a little. It wasn’t as though the clothes he wore restricted him. They were snug. That’s all. Very snug. The blouse that showed off his shoulders had a neckline that cut across his obviously masculine chest yet, as he admired himself in the mirror, he adored how the floral pattern flowed down past his obliques. He wore a singlet under the blouse. It was black and provided a foundation that let the pattern shine, in addition to giving his body much more slender appeal.
The pair of tight, form-fitting jeans he wore made his hips and butt look good. As he admired himself in the body-length mirror in the store changing room, he considered that the trouble he got forcing them up past his thighs were definitely worth it.
“Alright,” he said to himself, taking another breath to steady his nerves. He pulled the curtain back that separated the dressing room from the rest of the store and stepped outside. The heels of the open-toed booties he wore clicked against the floor as he paraded himself out to where Sandra was sitting. He balanced well on the four-inch heels and was proud of that, something he had developed after years of practice.
“Wow,” Sandra said, “you look great!”
Kevin held on to the elbow of his opposite arm. “You think so?” he asked, his voice meek but hopeful that he had genuinely impressed her.
Sandra stood up. Even with his heels, she was still half-an-inch or so taller than he was. “You look absolutely darling,” she said, walking over and taking Kevin by the hand. She focused on Kevin’s face and furrowed her brow slightly.
Kevin’s cheeks flushed upon being so closely inspected. He was already embarrassed by the curious glances of onlookers who spoke in hushed whispers. He could see more than one person make surreptitious attempts to snap pictures of him and hoped he didn’t get home to find that photos of himself circulating on social media.
Sandra, on the other hand, did not seem phased by the attention he was bringing to the pair. She had convinced him to come shopping for clothes with her, reassuring him that it would not be an issue. Kevin had acquiesced but now realized that Sandra’s warped perspective on the situation came more from her higher level of self-confidence or, perhaps, her general aloofness when it came to other people.
“Sandra,” Kevin said, talking through forcibly pouted lips as Sandra pressed her thumbs into his cheeks. “People are staring.”
“Let them,” Sandra responded nonchalantly. “I told you that you’d look cute in these,” she said, apparently talking to herself more than to Kevin. “Good thing we bought them on the spot because I definitely don’t want to get in that line again.”
Sandra was referring to the line at the cashier’s counter where she had paid for everything they had bought on this little shopping spree together. Aside from the clothes Kevin was currently wearing, she had several bags of her own.
They left the store together and Kevin tried to keep his self-consciousness at bay while they walked together through the mall.
There were some staring and some taunting, mostly in the form of tongue-in-cheek catcalling but, same as earlier, Sandra paid it no mind. Her cavalier attitude made it easier for Kevin to relax and, soon after, he was almost as comfortable as he was when he cross-dressed in the comfort of his own home.
Together they made their way to a nearby beauty salon that Sandra frequented. She was on good terms with the owner and had already made an appointment, which explained why she was so particular about queueing up to check out earlier.
As with the clothing store and the rest of the mall, there were stares and whispers when Kevin and Sandra entered the salon but he was able to brush it off more easily now. He and Sandra got stations right next to each other and chatted while being doted on by the stylists.
By the time they were done, Kevin’s appearance had transformed. He looked at himself in the mirror opposite his seat and was amazed.
“How do you look?” Sandra asked.
“Great,” Kevin responded. The combination of a close shave, skin treatment, and makeup and made his normally masculine features sleek and feminine. A combination of contouring and proper shading had made him almost unrecognizable, apart from his hairstyle that, even though properly treated, was very ‘Kevin’.
“One more thing,” Sandra said as though able to read his thoughts. She gestured to one of the bags she had brought with her. The hairdresser who had been working on Sandra’s hair picked it up and removed its contents: a blonde wig.
“What’s that?” Kevin asked.
“Well it’s obvious, isn’t it?” Sandra replied. She stood up and walked behind Kevin, flattening his hair before placing the tips of her fingers at his temples. “We’re going to make you real pretty today,” she whispered. While the hairdresser prepared the wig, Sandra leaned in close. “I told you that I have a surprise for you.”
“Wasn’t today the surprise?” Kevin asked. “Sandra, I’ve had a lot of fun today, really. You don’t have to do any more.”
Sandra laughed. “I know I don’t have to,” she said. “We’re friends, right? I want to.”
“I can’t thank you enough,” Kevin muttered.
“Oh,” Sandra said, “but you can.”
She stepped away as the hairdresser took her place. She applied the wig to Kevin’s head and remained still throughout the process, still lost in thought as to what Sandra meant by her words.
“There!” Sandra exclaimed once the hairdresser was done. “She looks pretty, doesn’t she?”
“She does,” the hairdresser responded. “Very…chic.”
Kevin could see in the mirror that Sandra had a very satisfied expression on her face. “I think,” she said, “we need to come up with a name for you, don’t you think?” She took the strands of the wig in her hands and fussed with how they lay but eventually gave up, finding the hairdresser’s work to be satisfactory. “How about…Jessica.”
“Jessica works,” the hairdresser chimed in, but it was clear to Kevin that Sandra already had the name picked out even before she suggested it.
“Do you like that name?” Sandra asked, leaning close and whispering into Kevin’s ear. “Jessica. How does it sound?”
“It sounds…” Kevin hesitated, looking at Sandra’s reflection in the mirror, as well as the womanly visage he now presented. “It’s sounds great.”
“Good!” Sandra said. “You owe me now, Jessica. Think you can do a favour for me?”
“Y-yeah,” Kevin stammered. “Anything you want.”
“Good.”
####
Kevin and Sandra had lunch together. Now presenting as Jessica, they were free from the curiosities of those around them. When they left the mall, a group of men had even flirted openly with Kevin which not only made him happy, but very curiously aroused.
“Looks like you’re quite the hot little thing,” Sandra had said as they walked together towards her car. There had been a suspicious tone in her voice at the time, but Kevin wasn’t at the time able to determine what it had meant.
His and Sandra’s afternoon was mundane. After shopping, he had joined her for some errands before heading to the house she shared with her husband, Maurice.
Maurice was someone Kevin hadn’t always gotten along with. Partially, it was because of his unreciprocated feelings towards Sandra, but it was also that Maurice had always intimidated Kevin.
He was taller, in better shape, and more successful as a man than Kevin was. That didn’t sting as much as the fact that Sandra had met Maurice only a week after turning down Kevin’s advances, citing that it wasn’t the right time for her to get into a relationship.
Given time, Kevin had learned to accept the situation and even thought Maurice to be a good match for Sandra in the long run. He provided a lifestyle that Kevin couldn’t, and Sandra seemed genuinely happy. Still, sitting in their living room presenting as Jessica only exacerbated exactly how vast the difference there was between himself and a man like Maurice.
It was a few hours before Maurice came home from work. Sandra introduced Maurice to ‘Jessica’ and despite the nervousness, Maurice was more than cordial.
Kevin was unsure that Maurice couldn’t tell that under the makeup and form-shaping apparel was Kevin. More than once, he caught Maurice glancing curiously in his direction while Sandra was distracted. He also couldn’t figure out exactly why Maurice’s scrutinization not only made him blush but made him squeeze his thighs together in an attempt to hide the stiffening bulge between his legs. It was one of the few times that Kevin was grateful that his manhood was less-than-imposing.
Dinner was had. And a bottle of wine was shared between the group as they sat together in the living room. Sandra and Maurice dominated the conversation, which Kevin was relieved over since ‘Jessica’ did not exactly have the deepest history to draw from with regards to anecdotes. Kevin simply played along, laughing at Maurice’s jokes and stories that more than once included himself.
“So, do you have a boyfriend?”
Kevin snapped to attention. “What? Sorry.”
It was Sandra who had asked. She had a sly look on her face as she sat, curled up on the sofa next to her husband. “I asked if you have a boyfriend.”
“N-no,” Kevin responded. He was now comfortable speaking in his ‘Jessica’ voice. He was concerned that Maurice would find his voice odd, but he didn’t seem to notice. He probably thought that Jessica was a woman with a particularly deep or husky voice and had put the matter out of thought. “I don’t have a boyfriend,” he affirmed, “haven’t had one for a while.” Kevin let out a nervous chuckle, sipping from his glass to signal Sandra that he wanted this line of questioning to end.
“That’s too bad,” Sandra said. “You’re pretty, you should have a boyfriend. Isn’t she pretty, Maurice?”
“Yeah,” Maurice said. He parted his legs suggestively as he spoke, and Kevin couldn’t help but glance towards the fork of his legs where a sizable bulge grew down the leg of his pants. “She’s hot.”
“Jessica,” Sandra stated.
“Yeah?”
“Maurice just complimented you. You should return the favour.”
Kevin was confused but decided to play along. “You’re very handsome,” he said, laughing nervously.
“Thank you, Jessica,” Maurice said. There was something about the way the tone of Maurice’s voice that made Kevin nervous.
“Being married must be nice,” Kevin muttered in an attempt to move the conversation along.
“It is,” Sandra said. Her fingers were in Maurice’s hair, stroking at his temple in a manner similar to how she had done to Kevin in the salon. “A bit boring sometimes, though. It’s why Maurice and I have an open marriage.”
Kevin almost spat his wine out. He had known Sandra for ten years but didn’t know she was into swinging. He almost felt betrayed, considering that Sandra knew his secrets. At least when it came to sex. “An open marriage?” he attempted to clarify.
“Well…not open, per se.” Sandra moved her hand down Maurice’s chest and let it continue further until her fingers were massaging the bulge between his legs. “Maurice has certain tastes and…desires. And I like providing him with what he needs. What do you think a man like Maurice needs, Jessica?”
Kevin didn’t respond immediately. He was busy with his eyes transfixed on the stiffening bulge that had almost doubled in size at Sandra’s touch. “Umm,” he said, attempting to buy time, “I can only imagine.”
Sandra smirked and leaned into Maurice, kissing him deeply. Kevin didn’t know what her plan was but remembered her words from earlier in the day as he watched the husband and wife kiss on the sofa opposite him. He shifted uncomfortably, attempting to hide his own erection with crossed legs as the sight he had fantasized over while masturbating so many times played out before his very eyes.
Sandra’s lips moved to Maurice’s chin, then his neck. With a final glance towards Kevin, she lowered her head to his waist and fumbled with his belt, button, and fly before pulling his cock out. It was an impressive piece of meat, easily dwarfing Kevin’s diminutive cock. It was thick – almost as thick as Sandra’s forearm – and wrapped in thick veins. Sandra stopped paying attention to Kevin as she wrapped her lips around Maurice’s bulbous cockhead and worked on accommodating the monstrous shaft in her mouth.
Kevin wasn’t sure whether to look away or not. Whatever the appropriate response should have been, he was sure he had failed when he realized Maurice was looking at him with a satisfied expression. Sandra had moved to her knees and had already nursed Maurice’s cock to a raging erection. With Maurice’s hand on the back of her head for guidance, she had been bobbing her head into his lap for several minutes now. Such a loving-yet-vigorous blowjob would have made Kevin explode in her mouth within a minute or two, but Maurice remained composed even as Sandra’s saliva dripped down his length and coated his manhood.
“You like what you see?” Maurice asked when Sandra pulled herself from his member. She wiped her lips with the back of her hand and glanced towards Kevin again.
“I bet she likes it. You like it. Don’t you, Jessica?”
“Y-yeah,” Kevin stammered. “That’s hot. Real hot.”
“Wanna touch it?” Sandra suggested.
Kevin’s voice caught in his throat. He wasn’t sure what Sandra wanted him to say.
“Jessica?” Sandra asked, making sure Kevin had heard her.
“Yeah?”
“Do you want to touch my husband’s cock?”
“Yeah,” Kevin admitted.
“Do you want to suck my husband’s cock?”
Kevin swallowed. “Yeah,” he admitted once more, feeling his cheeks sting with shame. “Yeah, I do.”
“Come over here,” Sandra said. Kevin felt himself stand up. It was as though he was no longer in control of his limbs as he made his way over to the pair. “On your knees,” she further instructed. Kevin didn’t hesitate to comply.
Maurice remained still; eyes transfixed on Kevin. The only part of his body that moved was his cock which throbbed eagerly.
Kevin obediently dropped to his knees, placing a hand on Maurice’s parted thighs to support himself. Sandra took hold of the monster cock and pointed it towards Kevin’s face. It appeared massive from a distance but now, up close and only inches from Kevin’s hungry mouth, it looked terrifying. Kevin wondered how Sandra managed to fit it in between her legs and, in an instant, an image of Sandra splayed on her back and moaning in painful ecstasy flashed in his mind. His own cock ached, and a very girlish moan escaped his lips.
“Suck it,” Sandra said.
Kevin did not need telling twice. He took Maurice’s cockhead in his mouth and sucked hard. He could taste Sandra’s spit as well as the salty precum leaking from Maurice’s tip. He was determined not to let a single drop go to waste as he wrapped his lips around Maurice’s shaft.
“Told you I’d get you a good little cocksucker,” Sandra said.
Kevin glanced upwards. She wasn’t speaking to him but was talking to her husband who was laid back with a look of pleasure on his face.
“You like how she sucks your cock?” Sandra asked. She moved her hand from Maurice’s shaft to the back of Kevin’s head, coaxing him into taking more and more of the man meat. Kevin tried his best, but it wasn’t long before he gagged on the cock being lodged down his neck.
“God,” Maurice moaned. “She sucks so fucking good.”
Sandra giggled. “That’s right. She’s a good little slut.” She kissed Maurice while keeping her hand on Kevin’s head. She forced Kevin downward so he could no longer watch the pair kiss. Kevin was fine with the arrangement. Maurice’s praise spurred him on with enthusiasm and he sucked now without and inhibition, eager, even desperate to have Maurice spurt his thick, salty cum into his mouth.
Thankfully, Kevin could still hear the words coming out of Sandra’s mouth.
“Do you want to fuck Jessica, baby?” she asked in between kisses.
“Fuck, yeah.” Maurice replied. “You gonna watch?”
“Mmm…yeah. I want to watch you put this slut on her knees. Fuck her nice and slow for me. Only at first. Then I want you to hold on to her and really let her have it.” Sandra giggled. “Really slam that cock in her until she begs for mercy.”
Maurice moaned at Sandra’s words and Kevin could feel the cock throbbing in between his lips. Seconds later, several spurts of warm, sticky cum sprayed into his mouth. The load hit the back of his throat and Kevin sputtered, being taken by surprise at first and only afterwards attempting to recover. He sucked hard while Maurice bucked his hips uncontrollably.
“That’s right, baby,” Sandra said encouragingly. “Cum in that slut’s mouth for me.”
Maurice moaned one final time as his orgasm came to an end and Kevin pulled himself away after finally being released by Sandra. He sat on his heels, breathing heavily with a mixture of drool and cum dripping from his chin into the blouse that Sandra had bought him.
“Did you have fun, Jessica?” Sandra asked, winking slyly towards Kevin as she caressed her satisfied husband.
Kevin looked at the pair and swallowed. “Yeah,” he said, still unable to catch his breath. “Does this mean we’re even?” he asked.
“Not even close,” Sandra muttered. “Not even close.”
Source: reddit.com/r/eroticliterature/comments/byxkpl/jessica_emerges