Intro
It had been a long time since John had seen his old friends Alexis and Erin. They had gone to high school together, and had hung out in the same group with some other good friends. Both were very pretty girls and John always wished he had dated at least one of them, especially Erin. She had been one of the knockouts of their school, with soft blue eyes and dirty blonde hair highlighting a cute face that was capitalized by beautiful soft lips. She had great tits, but her best asset was always well…her ass. It was nice and big and perfectly rounded, hovering above powerful thighs she used playing for the school’s volleyball team. Oh how John had spent time watching those games and fantasizing about what was underneath those short athletic shorts!
Unfortunately, back in high school while he was popular amongst his friends and classmates, he never did have a very good edge with girls in school. It had taken going to college for him to really quit being a pussy, to be frank, with the ladies. As a result, one of their mutual friends had dated Erin while Alexis had dated other guys and John was left out in the cold. Still, though it was never sexual he developed good friendships with them both over the years. So he had been excited to accept a job offer back in his hometown a year after graduating college, where Alexis and Erin both still lived.
A few months had passed since he moved in and “gotten settled” when he saw Alexis had started a cosmetics business out of her home one day on Facebook. That was the catalyst he needed to make contact once again. After talking to her on the phone, it was decided that he would come over for a pregame at 8 on Friday before they went downtown, and she would be sure Erin would be there too! Needless to say, John was excited to once again see his old friends.
Ch. 1
“It’s so good to see you!” Alexis flung her arms around John just as quickly as she had flung open her door. “It’s great to see you too!” he said, “It’s been too long”. She still looked the same as ever. Black hair with dark eyes perfectly touched with makeup, you can tell she had gone to school for it! She was shorter than Erin, and she had always been a little heavier too, but her large breasts and awesome persona made her attractive then as it did now.
After pleasantries had been exchanged, she welcomed him into her quiet little house in a neighborhood off downtown. She beckoned him into the den for a drink. “I hope you still like your whiskey” she said, pulling out a bottle of Maker’s. “Alexis you know me too well” he responded. Maker’s and coke all around was the perfect drink for the occasion, and one of their favorites from high school. “Erin should be here any minute” Alexis said, “so I’ll fill you in on the news before she gets here”. “Oh no, what’s she got into this time?” “Well, it’s really not that bad, she’s just coming off a bad breakup. Apparently the guy hit her, so naturally she broke it off. But she’s on kind of an anti-man kick at the moment, something about her not feeling safe around them. Don’t worry though, she’ll be glad to make an exception for you” Alexis said with a smile. “Well that’s just awful” John said, “I’m glad she ended it, she can certainly do better than someone who does something like that”. “Exactly” Alexis responded, pouring a bit more alcohol into her glass. “Oh look, here she is now.”
Erin walked in wearing a dress that hugged her body in the way only top tier girls can pull off. She was stunning, and her smiling face made her eyes look ready to melt anyone she met, and it took a second before John stood up to greet his old friend. “John it’s so good to see you!” she said, giving him a hug. The feel of her breasts against his chest felt amazing. He wanted her to never stop, but almost as it had begun it ended. “Here let me get you a glass!” Alexis said, stepping into the kitchen. That gave John and Erin a chance to greet each other and find out how each was doing. Erin was waitressing now, surprising since she had a nursing degree, but John didn’t question it. John was working in a bank, the standard 9-5 grind. Alexis returned with Erin’s glass, and soon the three of them were talking it up with whiskey and cokes in hand.
Throughout the evening, the three got progressively more intoxicated, and the conversation flowed as if they hadn’t had any time pass at all. They alternated between conversation and a casual drinking game or cards. John was starting to feel a bit of a connection between himself and Erin…he was getting the vibe it was mutual as well…but no, he was drinking and he wouldn’t let that delude himself into seeing something that wasn’t there. Still, every time they made eye contact and he saw into those beautiful blue eyes…”Oh wow it’s already 11!” Alexis yelled in the middle of conversation as she looked at her phone. “We should be heading downtown” John said, slightly disappointed as he was enjoying the three of them just talking and playing cards. “Yeah” Alexis said distractedly while looking at her phone, but then smiled and said “look who just texted me” while handing the phone to Erin. Erin began to laugh “what is this guy??” “I have no idea” Alexis said, laughing, “but I’m getting paid three times my normal rate”. Intrigued, John asked “So Alexis are you sure your only job is make up?” “OH stop” Alexis said laughing, “John, seriously this guy is too much. He’s actually a client believe it or not. He’s coming tomorrow to have me professionally makeup his face and beautify him. Apparently he wears drag and shit or something. He says he’s not gay and it’s just a kink or something, but all I’m saying is he’s paying me above my normal rates since it’s so weird. He’ll do it though since I work out of my house aka he doesn’t have to go in public.” Erin started laughing some more when she saw the look on John’s face. Now it was his turn to laugh. “No fucking way” he said, “I refuse to believe this is real”. “Look at the texts!” Alexis said as she handed him the phone. He scrolled to the top of the conversation. Alexis had named the contact “Girly Boy”.
Girly Boy: Hi this is for Miss Alexis. I’m interested in having you do makeup and hair but…do you only do women?
Alexis: Hi there! I do makeup and hair for everyone, are you interested in a package for a younger girl?
Girly Boy: Well actually miss…I’m a guy. I’m sorry I’m so embarrassed I could only work up the courage for a text. I’d really like you to make me up, and I’d be willing to pay double.
Alexis: Ok, is this a joke? Erin is that you? Ryan?
Girly Boy: I promise it’s not a joke…but I’m sorry I bothered you Miss Alexis I should have known better.
Alexis: If this is serious, in the effort of getting it out there I will do makeup on a guy, but I’ll be honest I’ve never done it before so idk how it will turn out, but I want triple my usual rates.
Girly Boy: Thank you so much Miss Alexis, I promise I’ll be good whatever you do will be great. I will pay triple.
The rest of the conversation was about Alexis saying it was bullshit while “Girly Boy” assured her he was real. He certainly had a submissive tone, while Alexis adopted a more domineering one. John wasn’t that surprised knowing her personality and Girly Boy seemed to enjoy the dynamic. He stopped read the texts after he got the gist of it.
John looked at Alexis. “Holy shit!” he said, handing her back the phone. “So what is he gay or something?” “No” Alexis said, “He’s called a Sissy. It’s a fetish. They’re guys that like to wear dresses and panties and act like women. Me and Erin looked it up online after I had him explain why the hell he wanted to come and get makeup put on him.” Erin nodded her head to confirm what Alexis was saying. “Wow” John said, “He’s coming tomorrow? Are you sure you’re safe with this guy? He’s obviously into some weird sex shit.” “No they’re all, like, really submissive to women” Alexis said, “I’m telling you if you look at some of the shit these guys are into there’s no way a Sissy would ever hurt a woman.” Alexis reactively made a quick glance at Erin. Erin seemed momentarily lost in thought as she nodded her head with an almost longing expression on her face. She stopped and then she looked at John, and for the tiniest fraction of a second there was a look of desire in her beautiful eyes. “It’s ok John, we warned him one of her friends would be here, so I’m going to come and watch the whole thing” Erin said smiling. “Do you want me to be there?” John said with a serious look on his face. “Aw John, you’re always so helpful. No I’m pretty sure he would bail if another guy was there, and I’m telling you, there’s no way he’s a danger to women. Plus Erin will be here and we’ve got mace.” Alexis said with a smile. She had always been adventurous; he wasn’t surprised when it bordered on sexual things as well. “Well you know I’ll do whatever I can to help y’all” John said with a smile. With that Alexis and Erin got a devilish grin on their faces and looked at each other. “What?” John said with a smile, knowing they had something in mind.
“Well…” Alexis said, “If you really wanted to help us, there is one thing that would be absolutely huge.” “Well what is it?” John asked, “I’ll do it, I’ll do whatever.” He wanted to reconnect with these girls, and see Erin tonight especially made him ready to get involved in things they were doing. Still, how much of that statement was the alcohol talking? Erin and Alexis looked to be calculating that question. It was one John might have given thought to as well. “Well” Alexis began, “I’ve never had a client like this before, and while I’m confident I can do it, I’ve just never put makeup on a guy’s face before…” She gave a little smile as she said it, half amused at her proposition and half nervous expectation of John’s answer. It took a second for John to realize what she was saying, that WAS the alcohol coming into play, otherwise he should have seen this coming a mile away. “Oh…” John said, his face turning from excited to negative rather quickly. “I don’t…” he began, but then Erin cut him off. “John” she said, sitting up straighter and leaning over the coffee table towards him. “It would mean so much to Alexis and I. We’d be very” – she opened her legs slightly, her dress allowing a fraction of a second glance at her panties if you were looking from the right angle – John’s angle – “grateful if you could help both Alexis and ME out by just doing this one little thing.” She emphasized how it would be helpful to her specifically. If John had thought there was a bit of a spark throughout the night between them, now he was certain. There was a tense stillness in the room as John processed everything. Nobody moved. “Ok” John said. “I’ll do it.” Alexis and Erin looked at each other and smiled. “Thank you so much John” Alexis said, “You’re such a good boy.”
Ch 2
It was now just after 11, and the alcohol was flowing through all three of them. Alexis was so excited. She excused herself to “get things ready” in her studio room at the opposite end of the house, down the hallway from the dining room. Erin stood up from her chair and walked to the opposite side of the coffee table, sitting down next to John on the couch. John poured more alcohol into his cup from the near empty bottle of Maker’s. He was nervous considering what he’d just agreed to, and probably regretting his decision. How could he hope to get with Erin if the first night he sees her in so long he spends it putting makeup all over his face? What was he thinking? “Are you nervous?” Erin said with a smile. “I remember the John from high school was usually nervous around me.” She reached over and put her hand on top of John’s hand that was resting on his knee. He looked over into her beautiful eyes. She was so gorgeous. “Now now don’t go reminding me of that” John said. “I’ve spent too much time redoing my actions with girls in high school in my head.”
“Oooh have you now?” Erin said mischievously, “and would you have done some things differently with me?” She was leaning in towards him now. The tension between them was rapidly mounting. He took a swallow from his cup. “There’s no need to be nervous around me” Erin said, and she leaned in and kissed him. Her lips were softer than he could have imagined. He put down his cup and placed a hand on her back. She held the other firmly on his knee. They broke for a second then kissed again. It was everything John had dreamt about after the volleyball games. The goddess from high school was kissing him at last.
“Ok you guys, I’m ready!” Alexis yelled from down the hall. Erin pulled back and John tried to follow her face with his. She used her soft fingers to push his chin back and giggled slightly. “I’ve been wanting to do that since I got here” she said, “come on now, let’s go help Alexis.” With that she took his hand and stood him up. He was intoxicated with more than just alcohol. He took one last swallow from his cup as she led him across the room. Down the hall they went until they entered Alexis’ studio.
The studio featured waiting chairs and a television set up at the far end near a door to the outside. There were two mirrors and chairs along a makeup counter to the right, a selection of women’s magazines on a shelf to the left. Next to the door Erin led John through was a table with a spread of cosmetic products and wigs. The real crown jewel of the studio however was a white leather chair; the first thought John had was that it reminded him of the ones at a dentist’s office. It was long enough for anyone to lay on completely from head to toe. It was raised so that once seated and reclined, the person in the chair would be about four feet off the ground, apparently the perfect height for Alexis to lean over you and apply her beautification technique. Alexis was standing next to the chair, palm outstretched towards the seat, as if she was showing off a new car in a showroom. With a wide smile on her face she said “Come on John, have a seat!”
Erin placed her hand on his back shoulder and guided him over to the chair. He turned around and sat back against the white leather, his head resting against the headrest, his arms resting on the arm pads. “Comfortable?” Alexis asked. “Yes actually I am, nice chair.” Alexis and Erin laughed. “Thanks John, I’m glad you like it” Alexis said. In a suddenly serious tone she added, “Now John, I want this to be as real as possible to how it’s going to be tomorrow, ok? We are pretending that you are my client for tomorrow afternoon. You’re right; I am going to take as many precautions for my safety as possible as I don’t know this guy, even though I think he will be quite safe. As such, I’d like to use these on you.” With that she reached under the chair and brought up a box John hadn’t noticed when he first looked at the room. It looked like it was more familiar with the bottom of a bedroom closet than a cosmetics studio.
“What is all that?” John asked. “It’s some restraints I purchased” Alexis answered. Sure enough, it looked like hospital restraints for someone’s arms and legs. I knew she was sexually adventurous, John thought, bought these for this one guy my ass. “These will ensure that guy doesn’t pull anything funny. I made it a condition of him coming here. Truth be told, I’m sure he will enjoy me using them. I’d like to figure out how they work on a guy’s body. I tried them on Erin when I first got them, but guys are bigger!” The thought of Erin being restrained in bondage on a chair by Alexis was so erotic it nearly made John gasp with ecstasy. Fortunately he had more composure than that for the time being. “Well, we’re already this far into it, might as well go the whole nine yards” John said and the three of them took a break from the tension with a laugh. “Such a good boy, I’m so glad you’re helping me” Alexis said, “Erin, would you help me restrain John?”
With that they took the restraints out of the box, putting them on his stomach. “I’ll get his chest, neck, and arms, you get his ankles and legs” Alexis said to Erin. As Alexis cuffed his arms at the wrist to the arm rests, Erin wrapped the restrains around his ankles to the leg rest. Once those were secure, Alexis moved and secured his chest to the back of the chair, pulling each tight. John wouldn’t be able to do more than wiggle in his seat against the restraints. He was at the mercy of the will of his two female friends.
“Just one more to go” Alexis said cheerfully as she started to secure the neck restraint “be very still”. He relaxed as much as possible, but the tension was unbelievable. He was nervous, embarrassed, but so turned on by these women putting their hands all over his body. Plus, he wanted to be a good friend. As Alexis was busy concentrating on John’s neck, Erin was securing the thigh restraints. Suddenly she grabbed his crotch and began rubbing his dick through his pants. It sent him into a full erection that caused his pants to pitch a noticeable tent. He went to raise his head and look down at Erin but Alexis pulled the restraint at the exact same time, locking his head back against the headboard. Erin stopped groping his crotch and pulled the restraint tightly into place. He was now officially locked in to the chair. Erin joined Alexis in his view and smiled at him. He was too overwhelmed by everything to smile back.
“Ok John, all strapped in!” Alexis said “is anything too tight?” The neck restraint felt like a tight collar, but it wasn’t too tight. He wanted her to secure tomorrow’s sissy as much as possible if he couldn’t be there for them. He could barely move anything else on his body. “Now I want it to be tight, so I want you to struggle as much as you can, that way we can see if anything needs to be adjusted. We don’t want anything happening tomorrow do we?” Alexis and Erin watched as John struggled against the restraints as much as possible. He couldn’t move his legs really at all and had a range of maybe two inches on his hands. He could do little more than grip the arm rest. He couldn’t look down at his body. He was stuck. “I can’t move anything” he said. “Well, it looks like sissies aren’t the only ones who enjoy being restrained!” Alexis said with a laugh. Oh shit, the erection Erin gave me! Of course she’d notice it, real funny joke Erin. John looked at Erin who just smiled devilishly.
“Ok, let’s begin” Alexis said, becoming more serious. “Now John, I want to earn a good tip off the guy too. If he comes back regularly, it will really help me out at three times my normal rate. In order to make that happen, I want to practice how I’m going to act with him. I’ve been reading about these guys on the internet and they’re totally into being controlled by their girlfriend or dominatrix or whoever. So please don’t be offended, but I’m gonna address you like I would a Sissy. Got that, Sissy?” Erin laughed. John felt himself blush a little, but then again that could just be the alcohol which he now wished he had about ten shots more of. “Ok Alexis”, John said. “That’s Miss Alexis to you, Sissy!” Alexis shot back. “Don’t forget to call me Miss Erin” Erin added, giggling. “Yes don’t forget my assistant Miss Erin!” John tried to play it off, saying “Ok Miss Alexis, Ok Miss Erin. Sissy John is sorry for being disrespectful!” He said it jokingly, but Erin and Alexis looked at each other with smiles on their faces with slightly bigger eyes. “Good boy. I like that, Sissy John. I’m going to use that tomorrow with my client!”
“Ok Sissy John” Alexis said, “Now I’m gonna make you look nice and beautiful.” With that she went over and got her makeup kit and brought it on a stool next to her. She pulled a lever and John’s chair changed angles so that he was now almost horizontal. He was looking straight into a bright light on the ceiling, and had to squint his eyes or look at Alexis’ face. Erin went out of his view. “Ok now Sissy John, I need you to keep your head pointed towards the light until I tell you otherwise so I can see what I’m doing.” He did as he was told. He could hear the pop of plastic caps of products in her makeup kit. She began to dab a sponge into some product. “Hold still ok?” Alexis said. “Ok” John responded. “Ok, what?” She countered, looking at him and pausing. He thought for a second before remembering the game. “Ok Miss Alexis”. “Good boy”. With that she went to work.
For what seemed like an eternity, Alexis stroked his face with various sponges, brushes, and what felt like creams. She moved from his cheeks to his chin, from his forehead to his nose, every surface of his face she touched with some sort of brush. She would occasionally say comments calling him a “good sissy” or “good boy”. It was so humiliating to John. He would hear Erin in the background occasionally, but could never move his head to try and see her. Finally, she said “now for the final touch” and popped the cap off a tube of lipstick. Erin came into view; her face looked in awe as she looked down into his eyes. “Now Sissy make your best kissy face for Miss Erin” Alexis said. “Yes Miss Alexis” John responded. He puckered his lips and stretched them out, waiting for Alexis to paint them red. She carefully applied the lipstick. “Now push your lips together and blow a kiss” Alexis said. John did as she told him to do. “Well Erin, what do you think?” Alexis asked. “Alexis holy shit, he looks amazing!” “Let me see!” John exclaimed. “Calm down Sissy let me sit you up while Erin gets a mirror.” Alexis said lightheartedly with a smile. She sat up the chair so that John was sitting at a reclined, but more upright angle.
Erin went over and grabbed a mirror and slowly walked towards John. “I seriously can’t believe it” Erin said. “I do good work what can I say?” Alexis responded. John was almost embarrassed at himself for being intrigued at how he might look. Erin held up the mirror. Starring back at John was like the face of a girl with far too short hair. To Alexis’ credit, it was what he imagined a Sissy would want in a makeup job. Perfect lipstick, eye shadow, all that crap. “Wow” he said. “I can’t believe you did that to my face.” “Well I’ll take that as a compliment” Alexis responded “hopefully the real Sissy feels the same way tomorrow”. “I’m sure he will” he said. Erin was still holding the mirror, looking mesmerized at his face.
She suddenly pushed the mirror into Alexis’ hands. “Now it’s time John gets his thank you for helping us” Erin said. Alexis set the mirror down on the stool. “Oh yes, I think he deserves a BIG thanking.” Alexis agreed. Both of them were looking down at him sensually. Immediately the atmosphere in the room changed. John almost forgot he was covered in makeup, strapped into a chair. All he could focus on was the two beautiful women in front of him. Erin leaned down and kissed him. She hesitated for just a moment right before their painted lips touched, surveying his face with wild eyes. Then she dove in and consumed his red lips, attacking them with unbelievable furry. The kissing was so intense he didn’t notice that Alexis had unbuckled his belt, casting it aside. He felt a hand grabbing his new erection and stroking it slowly up and down; it was only then he realized his pants were down to the thigh restraint, exposing his cock and balls.
He felt Alexis’ wet lips kiss the head of his penis as suddenly Erin tore back from his face, John didn’t have time to process it. He closed his eyes as he felt Alexis lower her mouth and envelope his penis in a full blowjob all the way to the base of his 5 inch erection. He moaned in ecstasy and didn’t notice Erin raising her skirt and ripping off her panties as she threw them on the ground. He opened his eyes to her hip touching his shoulder, her beautiful eyes staring in lust down at his own. She raised her left leg over his head and shifted her body so she was hovering over his chest. He looked down to see her perfectly shaved vagina glistening wet. She gave him a moment’s show before shoving forward and placing his lips into her own, those powerful volleyball thighs squeezing each side of his head, the weight of her glorious ass on his chest and shoulders. He furiously began licking and kissing her vagina and clit. Deep into the sweetness his tongue would plunge, his whole body straining against its binds. He was completely controlled by these two beautiful women, but it was an ecstasy that defined the most erotic moment in his life.
That moment of bliss was perfect, beyond anything he could have imagined. Yet just when he felt he could be no more aroused, Alexis’ pace quickened. Her lips ran up and down his shaft. Up and down and up and down at a wonderful pace, all the while her tongue salivated and ran all over his head, wonderful licks shooting darts of pleasure into his body. He could feel his orgasm building with each wonderful stroke. And he wasn’t the only one. Through the darkness of her locking thighs and ever-licked pussy, he could hear Erin’s moans begin to tell a tale of ecstasy. He moved his tongue to her clit and began and steady barrage of pressurized licks, her cries getting louder with every stroke of his tongue. Suddenly she moved back onto his chest fully, and he lovingly strained not only against the new weight, but also towards her beautiful, soaking pussy. She was feeling her own body, moving her hands from her face, with its closed eyes reliving the moment that had occurred seconds earlier, her open mouth where she held a finger to the corner for a second as her bottom lip ran under her top teeth, feeling the sensation. Finally her hands worked down to her tits, barely contained by a dress that was hanging on by a single shoulder strap. Her cleavage beckoned as she pushed them together, her hands feeling where his hands should be, if he able to move them. She half opened her eyes and their eyes met, her knowingly sensing what he wanted, but was only able to have if she allowed him his desire. “Alexis, stop” she said, her grin never fading, a perfect bead of sweat moving down her forehead.
Alexis ceased her rhythmic motion, and he felt the harsh cold of the room temperature air mixing with the saliva on his cock. “No” he said, and he strained towards where he thought her lips might be, even if he could move a few inches at best. “I almost had him ready” Alexis said, disappointment on her voice. It was true, another few seconds and he would almost assuredly have blown his massive load right down her throat. “I want to finish him” Erin said as she leaned forward and pushed her breasts onto his face. He eagerly kissed and licked as much as he could. Then he felt Alexis’ weight leave his legs and Erin moved back, then off his shoulders. The two of them looked down at the sight below them. John looked mad with lust, his exposed penis glistening from Alexis’ saliva, straining just as hard as the rest of his body. Ironic, as it was the only free-moving part he possessed at the moment. His face still looked as Alexis had intended, well largely enough. His lipstick has begun to smear.
“I want his cum inside me” Erin said, her eyes looking absolutely ravenous. Alexis smiled wide. “And I want to see if that tongue works as good as it sounds”. They slowly moved to switch positions. Alexis kindly gave him a moment to see Erin’s soft lips kiss the top of his penis as her beautiful eyes looked up into his. She gave one big lick all the way from the base to the head before taking him fully into her mouth. Then, just as Erin had done, Alexis lowered herself onto his face, her wet pussy ready to be eaten. As he began his licks, Erin kicked it into high gear. She wanted his cum now. Alexis began to moan slightly, she too was ready to cum. “Eat my pussy deep right now!” She said as he gave him a second of air. She held her body for a moment and looked down at him, making eye contact with an expectant look on her face. “Yes Miss Alexis” he said and she lowered herself fully on him. “Good Sissy John” she said. He exploded the most powerful orgasm of his life into Erin’s mouth.
Let me know what you think! Lots more to come as things only escalate from here.