Chapter 1
"Do you think I have lost weight?" Kelly stood in front of her full length mirror. Kelly was a nice size 10, certainly in no need to lose anything. She tugged at the very loose band of her pink lacy knickers. "Look they are loose" she observed and she was right. Questions about a woman’s weight are always tricky and near impossible to answer correctly but her boyfriend Andy would have to try and answer as carefully as he could.
"No, you look good to me" he replied, it was not a relevant answer, but a safe one. Kelly turned to him; she was naked from the waist up, her big nipples stood proud on her C cup chest.
"No they look great" he answered, even after all this time he was still easily distracted by her chest.
"That’s not what I'm asking" she laughed "Look, these are loose."
"It’s probably the washing machine I keep telling you it stretches my clothes" he offered an explanation. She never remembered him mentioning it before, but it was plausible, it had to be something, her perceived weight loss had not been noticed in her tops or trousers. She shook it off.
"At this rate I'm going to have to buy new ones."
"Of course you will" Andy replied, maybe it was just a ploy to go shopping. "So what time will you be back?" he asked. Kelly was out on a girl’s night, they both had quite good social lives and whilst they did go out together often, they would commonly go out separately.
"Probably about 3" she replied.
"Ok, give me a call" he replied. "I can pick you up" he kindly offered.
"It's ok Max will give us all a lift, he's not drinking" she said.
"Is he going?" Andy asked in an enquiring tone. Andy was not a jealous guy, but Max was one of those guys that no man would feel that comfortable about their beautiful girlfriend hanging around with. He was a slim, black haired man, attractive to the point where even a guy could see his appeal, he spoke with a strong east coast American accent. He had been in England since he was a teenager but somehow he had kept a strong accent, possibly it was just a ploy.
"Yes he is going, I really don't know your issue with him" she replied.
"Well you know" he said, not offering any more explanation to his unfounded concern.
"Trust me, he really isn't interested in me" she reassured. It wasn't as if Andy was suspicious about Max and Kelly, he just found it a little strange that he would always accompany the girls on a night out. On the other hand he was happy he wouldn't be dragged out in the early hours, also that there was someone who would look out for the girls.
"What are you going to do ?" she asked as she started to dress. She had chosen another set of underwear, this set fitted perfectly.
"Oh I will just laze around, maybe watch something" he said.
"Uh huh" She responded. That was her typical response to his rather vague words. 'Maybe watch something' she knew that there was a high possibility of that meaning, 'I'm going to lie on the bed and watch porn all night' she knew what he did but it didn't bother her, she had caught him watching porn before, furiously masturbating his 7 inch cock. Rather than be outraged she had just helped him out as if it were, well guys have their needs, and if she wasn't about then why should she care.
Kelly always dressed well, certainly age appropriate and tonight was no different, she always took a little care, her skirt was not too short but enough for her to still look sexy. She studies herself in the mirror and was interrupted by the sound of the doorbell. She kissed Andy as she grabbed her bag and rushed out the house, Andy was left alone.
Chapter 2
It was barely past midnight when Kelly returned, one of the girls had been refused entry to the club and rather than go on without her, they all called it a night. Kelly opened the front door with the utmost care, if Andy were asleep the last thing he would want was a d*unken Kelly creating a huge racket. By the time she reached the bedroom door it was fairly clear that he was still awake, there is no doubting the sound of hardcore porn. She could hear a loud American accent "You like that don't you little bitch?" 'Ooh little bitch' she thought, what was he watching, something a little more hardcore than he liked to be himself in the bedroom. Kelly smiled, maybe she could have a little bit of role play, and maybe she could be his little bitch tonight.
Kelly placed her hand ever so slowly on the door handle, she thought through her opening line as a little bitch, and how his fantasy was about to be a reality. She pulled the handle down and threw the door open wide. She could not believe the sight before her.
"What the fuck" she exclaimed in shock, "Seriously Andy, what the actual fuck?" What she set her eyes on was unbelievable, he was alone, but she would have been less shocked, albeit more angry if he had found a genuine little bitch there on the bed with him. Andy looked fearful, and quickly pulled the quilt over him. He had managed to hide himself from view but had failed to shut off the video on the laptop, he scrambled over and flipped the lid shut. Somewhere in his mind he thought that the bigger reaction would be to the video, but that was not the case for Kelly.
From her initial screaming Kelly became quiet, her face still frozen in a look of shock. It was a form of check mate, they both realised that someone would have to talk first, but neither knew the words that would prove appropriate.
"Take that quilt off" She shouted, even at his size he looked frightened, embarrassed to comply with her simple request. "Andy!" she shouted once more. However this would end up Andy knew that he had been caught out and as damage limitation he removed the quilt.
"That’s why they are so fucking loose" she shouted at him. Revealed on the bed now in almost its full glory was a 6'1" man wearing Kelly's lacy turquoise knickers and bra. To the outside observer this would have been hysterical, the difference in sizes of the couple made it frankly ridiculous. Quite how he had managed to stretch the bra onto his wide chest was something to behold. The knickers whilst fitted, bulged under the strain of his still erect penis, the exposed head almost poking from the waistband. "What the fuck are you doing?" Kelly broke, her anger almost immediately dissipating into fits of uncontrollable laughter. She peered over and noticed the bedside 'fun' drawer still open. "Oh my god, have you been using my toys?" she blurted.
"No no, I just needed a wipe." came his bumbling explanation.
"Have you been sticking my vibrator up your ass?" she said more in jest than anything, however given what she had stumbled upon it was doubtful that anything now would shock her further.
"No, I'm not fucking gay, I just..." He tried to explain.
"Well you are the one on our fucking bed in my underwear, what do you expect me to think." her point was valid. "Oh my friends are going to love this." she finished. Before he could even react she had taken her phone out and snapped a quick picture.
"Kelly! What are you doing?" he cried, covering himself once again.
"Just going to show everyone what you get up to" she laughed.
"Don't you fucking dare" he scowled jumping out of the bed. Kelly held the phone behind her back out of his reach, as he tried to retrieve the phone. From the outside it must have been an even more humorous sight, seeing this big guy jumping around helplessly in very ill-fitting lacy underwear.
"Uh huh" she said mockingly, "Be a good girl, I won't share it, I promise" she told him. Andy knew she was telling the truth, if nothing else she had always been honest, and whilst he was unsure of her motivation, he knew that he was relatively safe. "I'm going to bed, and you can get those off.... and no not in that way" she said with a smile. Kelly disappeared into the bathroom as Andy took off the underwear and rolled back into bed. Kelly re-emerged from the bathroom in a full covering long nightdress. She turned off the light and climbed into the bed turning away from him. He moved over into the spoon position his still erect cock pressed against her ass. "You can stop that" she informed him.
"I’m so horny" he confessed.
"Andy, I couldn't be less horny now if I tried" she explained "you are lucky you are not sleeping on the sofa, dirty cunt!" her choice words ended the conversation right then and there, she knew that she meant what she had said.
Chapter 3
Saturday breakfast was the first time in the week that Kelly and Andy actually got to sit down and talk, they talked in the week in the evenings but this was a time to sit down and mull things over. Nothing had been said since they had woken, it was as if the events of the previous night had not even occurred, yet to believe that would have been a mistake, Kelly certainly was not going to bring up the subject.
"I'm sorry" he opened the conversation.
"What for?" Andy thought for a split second that he was off the hook and she wanted to erase everything from her mind, but she continued; "For wearing my underwear? Or for being a big girl?" she mocked. She was not angry, or even shocked, the night’s sleep had done wonders and now it just amused her.
"It's not like that" he answered
"So what is it like Andy, please tell me, I really want to know" she asked
"I just like the feeling, you know it’s different" he tried to explain. The words themselves did not seem to fit the masculine man now sat opposite her.
"Are you going to do it again?" she delivered her next short sharp question. Lying would probably have been the best option here, yet her chose to be open with her.
"Just once a week, if that’s ok?" he asked hopefully.
"Really?, you are actually going to do it again?" the shock had returned but Kelly kept herself composed to conduct an adult conversation, she needed to know his feelings even if she didn't like or want them.
"Just once a week, I'll buy my own" he blurted, as if the offer would radically change her opinion on the matter.
"Damn right you will" she confirmed. "Oh and I let you do this, and you let me do what I want" she offered a deal.
"Yes, yes anything" he agreed, without seeking the full clarification of what she was actually saying.
"Ok, no more talk about it, I will let you know when you can do it next" she finished.
"Of course" Andy said with a smile, his secret was out of the bag, and he felt as if a huge weight had been lifted, now he would be able to express himself, on her terms, but still that was more than he had ever hoped for.
Chapter 4
Andy sat on the edge of the bed, his smile showed just how pleased he was with himself. He had done as Kelly had requested, and ordered his own underwear. It was nothing like Kelly had herself, a purple silk set, he had found them online, on a site specifically for cross dressing and the size guide had worked perfectly.
Tonight would be the night he got to wear them, a text message from Kelly earlier told him to follow the instructions she had left clearly, and he was doing exactly as he was told. He didn't fully know what to expect, he had signed a sheet of paper allowing Kelly her unspecified anything, but it was worth it to feel the freedom he craved. It was not just Andy who had been online shopping, Kelly had done the same and laid out on the bed, were her own purchases. A set of keyed leg restraints, two pairs of handcuffs, quality ones with proper keys, there was no self-release catch as you find on the novelty ones, and a whip, it was clear what was in-store for him, and his cock swelled with excitement.
The wait was finally over, the home phone rang just the once, just as he had been advised, that was his five minute warning to be ready. Andy fastened the bra before putting it on, he had not yet mastered doing it up in position, but as he had nothing to put in them it was easy. He had considered filling them, but socks were even less convincing than his flat male chest. He slipped into the knickers and tucked his cock inside, there was no way he could be convincing with such an obvious bulge. Finally he set about the restraints, he needed to be in the doggy position, with his hands free it was an easy task to achieve. Finally he attached the handcuffs to the bed, and after attaching the first one, he threw the keys to the floor, it wasn't easy but he managed to use the bed for leverage to fasten the second, he took extra care not to fasten it too tight as he would have no way of loosening it. Andy tugged at the bindings, yes he was secure and at her mercy, now all he had to do was wait.
Kelly must have been just the other side of the door when she made the call, as her entrance was timed to perfection, five minutes, to military precision. Andy could hear her shoes on the floor, as he waited and waited, she was noisy, as if she was not alone, finally she stepped into the bedroom by herself.
"What do you think?" he asked. Behind the facade of her expressionless face her mind was screaming out 'what the fuck are those ?, shit my mum wouldn't wear those' whilst the set appealed to him, it was not to her taste or liking, but she kept her mouth firmly closed on the matter.
"Let's get this straight I'm in charge, tonight you are just a little obedient girl, you talk when I talk to you.... OK?" she informed him. Andy nodded in agreement, after all he knew the score, and he had handed over all control to her, for tonight anyway.
'Wow' he thought, this is exactly what he wanted, well if he had the choice he would have opted for her to dress as a dominatrix, in full leather, but it was not his choice and he knew his place. Instead she wore a short brown denim skirt, black tights and a tight fitting white blouse, her black bra underneath was hugely apparent. She walked around the bed studying her little girl and appeared in deep thought as to how she should proceed, if only he knew, nothing was random, everything had been planned.
Kelly stooped and picked up the leather whip, it was a novelty one, the kind you would find in Ann Summers, but novelty or not it had the potential to hurt.
Whack, the tip of the whip impacted his ass hard, it was a pain unlike anything he had experienced, a sharp pain and a following stinging sensation 'Ok so whips are not as much fun as I expected' he thought.
"So little girl, are you going to let me do as I please" she asked in a stern tone.
"Yes Miss" he replied, there had been no need to use the word Miss, it wasn't in her instructions, but he felt a bit of improvision would only improve the role-play.
"I can do anything I like, to me, to you, anything?" she asked.
"Yes Miss, you can do anything" came his groveling acceptance. Kelly bent down to observe his bulging package.
"Oh you like being a helpless girl don't you" she mocked seeing the state he had found himself in. She could clearly see a dark patch forming in the silk panties.
"Yes Miss, I like being a girl" he confirmed. Kelly grabbed his hard shaft in a brutal grasp, it was unlike any hand job he had experienced from her, but he liked her rough play. She masturbated his length hard causing his pre-cum to fill the panties like nothing she had seen before.
"Well it's not about that" she said as she released her grip "It’s about this" Kelly walked over to the bedside drawer. He watched as she pulled out a tube of lube, there was no fear in his face, it was if he had been expecting, wanting this to happen. Kelly lubed up her index finger, not hiding her actions in anyway. She walked to his rear and pulled the back of the panties to one side exposing his tight ass. Placing her finger at his anal opening she applied the smallest of pressure, her finger penetrated and slipped in with ease, there was not reluctance to her offending digit. It was a whole new experience, and this was just for Kelly, of course she had fingered herself, but never a guy’s ass, she did not even know if she was doing it right, but she carried on not concerned about him.
He was murmuring, it was not like her own personal anal experience at all, from the onset he was willing, and her suspicions were being proved correct. She slipped her finger deeper and deeper until the whole length was fucking her boyfriends ass.
"Oh you like that don't you babe, you like your girlie ass being fucked don't you" she toyed.
"Yes Miss, I like it" His admission amused Kelly, this would certainly not become regular bedroom play, but she fully intended on stretching him to his limits, literally. Kelly withdrew her finger and walked back to the drawer, this time producing a very small silver vibrator, she turned and presented it to Andy, his eyes seemed to light up at the prospect. Kelly shook her head and placed it back in the drawer, replacing it with a much larger rampant rabbit. From the vibrating ears it was over six inches long, nearly as big as his own fleshy member, maybe not the girth, but then again Andy had not yet managed to get his cock to twist and turn in such exciting ways. 'Well it will clean' she thought to herself, she had fully intended on using the silver one, but the reaction was not as she planned. Andy looked at it in a more cautious way, he had definitely tried the small silver one, she was sure of that, but this one, she had her doubts. Liberally she smeared every inch that would be inside him, with more of the greasy lube, she wanted to have fun with him, but not hurt him.
Andy had already learnt that any kind of protest would result in a heavy crack of the whip, but just looking at the toy made him quiz what would hurt more. Kelly’s suspicions were correct, on many a secret occasion he had experimented with the comparatively tiny silver vibrator of hers, and whilst he may have given a fleeting glance at the much larger rabbit, that had been as far as his curiosity had advanced. Andy looked behind him to the best of his ability, as she walked back to his ass. Andy jumped as Kelly added a generous drop of cold lube directly onto his ass. With her finger she smeared it around his tight puckered hole.
"You had better relax Andy, or this is really going to hurt" her words were delivered in an upbeat, even slightly sadistic tone. She placed the tip against him and pushed. Unlike before there was resistance, not just resistance due to physical limitations, he was clenching, as if he was scared of the imminent intrusion. Kelly pressed harder, there was no doubt in her mind that this was going to happen. "Relax, let me fuck your girlie ass." she firmly stated. Maybe it was the self admission of helplessness or maybe it was her words, but Andy relaxed. Finally his ass allowed the gradual ingression on the thick rubber tip.
"Fuck" he gasped as the toy entered his tight passage, His hands grasped at the mattress as if he was bracing himself. More and more pushed into his ass, she did not let up on the pace or pressure, this was going to go in, in one go. The more that went in the easier it became, Andy was panting wildly, if he was in any pain he wasn't saying it.
"Is it in yet?" he asked in hope.
"Nearly" she replied, it was part lie, of the 6 or so inches there as still another two to go. Kelly put her palm on the base and pushed the last two inches home.
"Fuck, fuck, fuck" he called. It wasn't pain, but it was a strange and somewhat uncomfortable feeling, it was like nothing he could have imagined, he felt full, he felt the compulsion to clench and eject the object from him, yet Kelly was holding it firmly in place. Slowly she began to use the object to fuck her boyfriend’s ass.
"You like that don't you, you like a big cock in your sissy little ass don't you?" Kelly taunted.
"Yes, I love it, I like my sissy ass being fucked" he confirmed. It was no lie, after the initial feeling, now he was experiencing pleasure. The pumping action massaged his prostate from deep inside, his near constant flow of pre-cum leaking from his sticky tip was the proof. Even not being touched directly he could feel how this could result in a satisfying explosion. Kelly reached below him and placed her hand on his wet sticky tip.
"You do like it don't you?” she gathered the largest handful of his sticky fluid with one hand, as she pressed the power button on the vibe. Kelly tucked the vibe back inside his panties, the elastic held it in place, burrowed deep in his ass, the vibrations still sending intense and pleasurable sensations through him.
"I'll be back babe" she said smearing his face with his own pre-cum. Still Andy did not react, she was playing her Role perfectly, and whilst she had claimed this would be about her, the pleasure was all his. He watched as Kelly departed the room, closing the door behind her. Andy stayed locked in position enjoying his girlie treatment, the sensations had his mind in a blissful place, it was not quite enough to send him into orgasm, but more than enough to keep him rocking on the edge.
Andy looked over as he heard the slight squeak of the door handle being turned. Kelly strode into the room in just a black lacy bra and knicker set, her long dark hair swept down over her back, her nipples quite clearly visible in her bra.
"Are you ready?" she posed her question.
"For what?" He replied anxiously
"This, Come on in" she called through the doorway. In casually walked a naked man, a naked man that Andy recognised, even without hearing his accent, it was Max. Max walked and stood side by side with Kelly. Andy gave a slightly despondent look, of all the things he had expected, it was not this.
"A 3 some, I should have guessed" he sighed, but it broke into a slight smile. Somehow in Andy’s mind he had believed that if he were to be involved in a 3 some, it would have been with another woman. He was accepting of his fate, he had chosen the freedom to dress like this in return for sharing his hot girlfriend but why Max, why the one guy that he had always had slight suspicions of.
"Yes something like that" she confirmed his suspicion. "Last chance to back out Andy" she stated.
"No, let’s do it" he said assertively, believing that his freedom was actually worth it. "But he's not fucking your ass" he added just the one rule, he didn't have exclusive access to her ass, she wouldn't let him near there, because as she had said, 'I'm not taking that big thing in my ass' "and condoms"
"Ok Andy, trust me he won't be fucking my ass, now shut up" she attempted to re-gain control of her sissy boyfriend.
"Oh and..." Andy winced in pain as the whip cracked harder than before on his ass.
"I said, no talking, you are going to use your tongue for something else" Kelly climbed onto the bed and threw one leg onto Andy’s shoulder, the other leg landed on his other shoulder, she reached down and pulled her knickers to one side exposing her moist pink hole to him, she was clearly and visibly aroused. Kelly used no vocal prompt as she reached up and pulled his head down onto her pussy, holding him with both hands and pressed him harder into her. "Now lick me like the obedient little slut you are!" she demanded. Andy could not reply, his tongue was already pressing into her wet hole. She prompted Max to join her at the head of the bed. "Are you ok" she asked with concern, even amongst all the action he was witnessing his cock still remained small and flaccid, exposed by his complete hairless appearance only acting to exaggerate his lack of arousal. "Come here" she beckoned him. Kelly leaned over releasing her grip on Andy’s head, but it did not deter him.
As Andy licked her, she slowly began to stroke Max's cock, she tried to coax him to life, and for a bit it worked, from being lifeless, it had a pulse, slowly the length grew, the veins and wrinkles began to erase. He was semi, but it didn't seem to want to grow more. Max looked concerned that he wouldn't function. "Close your eyes" she requested. Max complied, he felt the warmth of her soft mouth as it closed around his shaft. Further it grew, Kelly must have been sucking for several minutes, in truth it was longer than it would take to suck Andy to completion, yet still he was not in a fully ready state.
"No Andy" she shouted as he tried to flick his tongue against her rock hard engorged clitoris. The deep tongue fucking was bliss, but the clit play would certainly crack up things another level, and whilst she would cum, it wouldn't be now.
"Sorry Kell" Max said, his disappointment clearly audible in his voice.
"Andy, suck his cock" Kelly ordered.
"Are you serious?" he said in disbelief. Crack, Kelly was serious and he knew it, he just didn't know how to respond.
"Question me one more fucking time and I’ll whip your balls" she warned.
"It’s one thing you sucking his.." crack the whip impacted his balls, sending an excruciating sensation through his body, it was not like no pain he could imagine, worse than being kicked or being hit by a football there, his body clenched sending the still vibrating toy from his ass and onto the bed.
"Again Andy? Do you want that again?" Kelly moved to allow Max to get in a knelt position, Andy found himself eye level to another man’s cock for the first time in his life, was he ready to do this though? Crack the whip slammed into his balls a second time, almost at the bright red point of the first impact. Andy yelped and clenched his eyes tightly, as the pain rescinded he opened his eyes again. This time he didn't even question the action, he gingerly opened his mouth a little. He moved towards Max’s saliva coated head, which now just seemed so much bigger than before, he allowed an inch to penetrate his virgin mouth.
" Oh that's my willing little sissy slut" Kelly said encouraging her boyfriend. Andy knew how to receive a great blowjob, but giving one, he had no experience at all. He felt his mouth swell as he began to suck as he judged was expected. Directly there was no comparison, his thick long cock, was clearly much bigger than the 6 inches Max had to offer, but even this felt big. Still he sucked just the tip, frightened of the length. "Fuck his sissy mouth" Kelly taunted.
Kelly was calling the shots and both men were under her control, unlike Andy, Max complied to her orders with no questions. He began a soft thrusting motion pushing more of his length into his mouth. "Take it down" she instructed, willingly he allowed the deeper penetration, 4 inches of his meat was now plunging into his strong suction. Andy, would never reveal, but he was enjoying it. Even when he tasted the salty secretions of his pre-cum, Max was now fully erect.
Max withdrew his cock and its full potential now swayed in the air. Looking up Andy felt an unbelievable satisfaction, he had managed to achieve something even his fit girlfriend had failed to do.
"Isn't she a good little cock sucking sissy Max?" Kelly asked.
" Yes Kell, he is very good" Max confirmed. In the surreal situation he had found himself in Andy felt impressed that he had performed so well, in a way he felt more feminine than even the clothing had provided him.
"Are you ready?" She asked Max, as she handed him the leather whip. Max nodded his approval. "Fuck me" she demanded. Andy tried to move aside as far as the restraints would allow, to let Max in, literally in to his girlfriend. "No not Max, you fuck me" she said as she held his face in her hands. "Fuck me with your girlie cock" Kelly slid down the bed between his bound wrists and heavy manly thighs. She positioned herself by his self-lubricated solid cock and turned over, presenting her shapely ass to him.
"In your ass?" he exclaimed in welcome delight. If a threesome meant he could have her ass then he would welcome it wholeheartedly.
"No !" She stated firmly as she grabbed and guided his long thick shaft, "here" she helped him to her wet pussy entrance. It was a position not particularly suited for vaginal intercourse, but with an impressive length such as his, it was easily achievable. Andy pushed his entire length straight up into her soaking pussy. Kelly let out a gasp of pleasure, the position ensured his tip would brush her pulsating g spot sending waves of intense pleasure through her. As if spurred by the situation he proceeded to plunge into her inner depths with a ferocity that their solo love making had lacked, she was being fucked like she craved. However she needed to control things, to achieve the desired result, she would have to control him.
"Max" she called, she didn't need to instruct him any further, there had obviously been a conversation about how this would all play out. Max swung the whip onto Andy’s ass, not hard but enough for him to feel it, then again, and again. "Keep the pace Andy" she informed him as Andy slowed his thrusts to keep in time with the taps the whip provided. It was roughly about one slow push every second. Kelly looked over his shoulder to see Max preparing himself, he unwrapped a condom and rolled it along his shaft. "Your turn Max" she said. Andy immediately stopped. "No, no, keep going Andy"
"How is he going to fuck you?" Andy asked curiously. He could feel the bed dip as Max climbed up on the bed, yet still the realisation failed to sink in.
"Oh Andy, Max isn't going to fuck me, Max is gay" she dropped the bomb. The phrase was not random, it had been perfectly selected as a trigger point for the proceedings. Andy felt as the girlie panties were pulled to one side, for a brief second he felt a cold breeze on his ass, still lubricated from the earlier toy insertion. The cold feeling stopped the split second he felt a warm sensation. It held there for a moment as Andy pulled his cock backwards on his own outstroke.
"Fuck" he shouted as during his in-stroke he felt Max penetrate his virgin ass. Andy bucked a little as he tried to fight the intrusion. He was confused, he was frightened and slightly distressed, but bound as he was, he was in no position to stop it. Kelly rolled over onto her back as he exited her pussy. She held his shoulders tightly and stared deep into his fearful eyes.
"Take it baby, take his cock like the sissy you are" she mockingly advised. Her green eyes showed a wicked streak, a gleeful delight at the fate that had befallen him. "A good girl takes a cock" she continued. "Relax, relax" she told him, Andy calmed down. She placed her hands onto his ass and pressed him back inside her, she re-started the slow yet purposeful rocking. It wasn't the size that had disturbed him so greatly but the fact that now he was truly being treated like a sissy slut. "Yes Andy, that’s it, that’s good, yes?" she posed a question. The three of them moved together in unison, him sliding into her and Max gently taking his anal cherry.
Kelly released her hands from him and placed them back on his face, maintaining intense eye contact as she saw the look of fear dissipate, his eyes clenched tightly as Max's entire length pushed hard into him. "Oh you like it don't you?" she asked. It was not a leading question whilst his words could lie, his body couldn't and Kelly felt his cock swell inside her pussy with each insertion he received, it was so much harder than she could ever remember.
Andy thrust harder, causing Max to struggle to keep rhythm, anything that Andy did, then Max would have to match, and this meant that he would have to fuck him harder. Andy was enjoying it, really enjoying it, Kelly was enjoying it, and Max,well he thrived on sliding into this tight anal virgins ass.
Kelly threw her head back onto the pillow, watching the action was pushing her beyond her limits, she reached down between her legs and set about rubbing her hard clit. She knew Andy so well and knew that his breathing warned he was close to an impending explosion.
Simultaneous orgasm between two partners is hard enough, but Kelly was now tasked with trying to achieve this 3 ways, she knew that her own simulation could possibly match Andy's, but to bring Max off in time may prove tricky. She circled her clit with the juices drawn from her by Andy’s pumping shaft, her breathing rate increased as she felt the sweet feeling building in the pit of her stomach.
The room filled with noises as the pace increased, sounds of breathing, little murmurs from them all, the sounds of juices swirling inside Kelly, the slap of max's heavy balls impacting Andy's ass, muffled slightly by the knickers he still wore. Any apprehension had long passed, Andy even found himself pushing back against Max at the completion of each thrust. He hadn't even flinched when Max had gripped his hips.
"Fuck my girlie ass" he had even let slip, Kelly smiled at his obvious enjoyment.
"Yes, you like my cock in your ass girlie boy" Max retorted in his thick accent. Pounding even harder, his climax was also approaching and he did not want to be left out. The increased pace were more than Andy could take, his point of no return had passed and he was clinging onto his load clenching every muscle in his body, including his ass.
"Oh fuck, I'm gonna cum" shouted Max. Immediately he pulled his cock from Andy’s ass, the suction stripping the condom from his shaft. He lunged forwards and held his cock in his tight grasp, as a large spurt of thick white creamy cum exploded from his tip and left an impressive trail from Andy's lower back to his shoulder. The warm unfamiliar feeling set off a chain reaction, almost on impact Andy let go and relaxed sending a huge swirling wad deep into Kelly’s warm pussy. Kelly felt him bulge and the ripples of cum tearing through his shaft, the combination of her touching, the heavy intercourse and the cum treat she was having dispensed within her threw her into a convulsive orgasm.
Kelly screamed as an absolute pleasure swelled in her body. It was an orgasm of such intensity that she just wished to free herself from Andy’s pounding, however Andy pinned her in place ensuring she received pulse after pulse of his sticky cum. Whilst in many cases it may be the truth that the average male ejaculation is around a teaspoon, this was nothing like average, to Kelly it felt more like half a pint of his hot juice filling her, still he continued pounding, each outstroke seemed to pump the mixed juices from her depths and out onto the bed. Like a wounded beast Andy pushed hard into her one last time, raising himself up from the bed, his cock slipped from inside her, spilling juices all around. With a big intake of breath he slumped to one side face first on the bed.
Max wiped the last of his sticky expulsion onto Andy's soaked knickers before adjusting them back into place, barely covering his modesty and well used hole. He smiled at Kelly as he dressed.
"I don't think he will forget that for a while" he stated, as Kelly laughed. Max left the two of them exhausted on the bed.
Andy awoke, dazed and confused, as if he was coming round from a heavy hung-over state. He was still in the position he had been left in, still face first, dressed as a girl, and sporting evidence of the previous night’s debauchery. Max's ejaculation flaking on his flesh, Andy let out a pained groan.
" Good morning Princess" Kelly spoke, her words chosen to reflect the feminine state in which he still appeared. Andy groaned an incomprehensible reply, even with a full night of sleep he still fully felt the effects of his treatment. Andy rolled over to the edge of the bed.
" Fucking hell" he exclaimed as he rose to his feet, slightly stumbling. Kelly smiled as he waddled uncomfortably to his feet, his hand grasping his obviously sore ass. His autonomous morning glory visibly bulged in his knickers. She heard the shower run as she fondly recalled the excitement of his transition.
Andy returned looking refresh and rejuvenated, he stood in a towel, the women's underwear having being discarded now.
"Have you got it out of your system then ?" She asked the masculine man stood before her. His response was not quite what she had expected.
"Well I still want to dress like that occasionally, but no more threesomes please." he requested with a big smile.
" Ok, no more threesomes" she confirmed "but Andy, if you want to dress as a girl, you still need to be treated as one" she continued. "And I have something extra special for that" Kelly reached under the bed and pulled out an object, a purple strap on, maybe 6 inches in length. Andy smiled, a happy telling smile.
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