M had known for a long time that for her life was different. She’d had many relationships, she enjoyed the friendship and needed the warmth that came with getting close, but physically the sexual act left her bewildered. She’d had many lovers that could bring her to an orgasm but even then felt there was something missing, something far more pleasurable that could be achieved.
Over the years she’d taken chances, risks she would not normally consider. She knew there was a lot being put in jeopardy, that her health may have suffered. There had been a time when she’d woken with bruises on her neck and a lack of memory of the events that had caused them, but none of this satisfied that urge, that yearning. Nothing came close to reaching that utopia.
Then she met S. Like her, the man was different. It started as an online friendship in a chat room, one of the thousands of anonymous relationships that fill the internet in the depths of dark, cold nights. The only commonality in their vague profiles, M knew the area where S lived.
M enjoyed the easy conversation albeit restricted to words on a screen but quickly became bored and wanted to move on. It’s what she did. Then S showed vulnerability, when his persistent requests to speak went largely ignored he began to beg, offering anything to keep the relationship alive. In that M felt a vague buzz. It excited her.
Over the days that followed they continued to speak online but the pattern changed. M deliberately kept the time she was online spontaneous and random, demanding he leave regular offline messages but only occasionally responding. S continued to plea for more but obeyed.
The conversations quickly became sexual. S admitted he was aroused by all he imagined M to be, told her that he would masturbate while they were speaking online. M demanded that he post photographs, at first just of his penis but when she didn’t know if he was just copying images from the internet, she insisted he tie his cock in blue cord and post that. He complied without hesitation.
S confessed he occasionally wore women’s panties. When M started to question the feelings and emotions this man experienced he was at first coy. When M suggested she would not only let him wear her panties but would dress him in her clothes, he started to open up. When M persuaded him to imagine being taken shopping and bought shoes, stockings, basque, panties and dress, it unveiled a whole new world.
S’s messages became full of confusion and excitement. He confessed to imagining M spoil him with what she bought, pampering him by helping him bathe and shave his body, touching him by helping him dress. He said that he couldn’t find the words to describe how he might feel being dressed fully as a woman, but admitted to masturbating more frequently than he ever had before and enjoying prolonged orgasms, cumming like a horse as he crudely put it.
M didn’t know if this man’s sexual arousal was from some unfulfilled dream of being a cross dresser. When she pushed him to decide if it was a fantasy that he would ever act out in real life he became decidedly nervous. When she threatened to end their friendship he caved in immediately. He said he would do anything.
Those simple words changed everything. M knew she had control, absolute power to make this man do whatever she asked, whatever she imagined, and that obedience was a powerful aphrodisiac. M immediately became aroused. She had been turned on by sights and people before but she couldn’t remember the feeling being so instant. She felt as if her heart was missing beats. Her breathing became rapid. Her nipples grew hard.
When she stood, reached under her dress and slid her panties down her thighs they dropped to the floor heavy with secretions from her vagina. When she masturbated she reached a climax within seconds. It was intense and continued for what felt like hours. An orgasm like that is not something many women could forget or ignore. For M it was pure nectar, the food of the gods and something she had given up imagining possible.
M questioned if she felt any sort of true bond with S and severe misgivings about manipulating a man that was clearly vulnerable and perhaps unstable, but the feelings that existed in that moment of bliss were addictive. She knew she needed more and it seemed the easy route was by turning this fantasy into reality.
M plagued the man with questions. She became unrelenting in making demands, testing him to see if he would be truthful, checking constantly that he understood where the conversation was headed. The more she wanted the more he gave and the more the anticipation overwhelmed her. She started to masturbate regularly hoping for another orgasm like the first, but the more that eluded her the more she knew what she had to do.
They set a date. They traveled independently and met in a hotel, far enough that neither would be recognized by someone they knew yet close enough to not waste time. M had done her homework. She had chosen somewhere local to boutique dress shops and near to bars and nightclubs. She had picked a hotel with a spa and booked adjacent rooms. She knew S would be hoping to share a bed with her and probably imagined he might fuck her, but if that happened M wanted it to be on her terms not his.
They arrived early and checked in for their spa appointments; A facial, manicure and eye-brow tidy for them both. It was for M a routine luxury but she worried that S may get cold feet if she were not present. Then shopping; red basque and panties, black stockings, and an orange dress. M was conscious of the hushed whispers and strange looks when she explained that S would be trying them for size and again worried the man would bail-out, but she kept control, all the time getting excited at the transformation taking place.
Then came the shoes. M knew that S would have opted for heels and actually thought they would mould his legs into the most perfect shape but they had to be practical. She planned on enjoying a night on the town, flaunting the beauty of this man-woman, watching the reaction of the crowd. S had to be able to walk, comfortably and elegantly.
Next M helped S to bathe and shave, showing him how to use a razor on his legs without cutting himself. It was the first time M had seen him completely naked. His was not the body of an athlete or a porn star but he was in good shape and clearly took care of himself, a trait that M admired greatly. She found herself getting aroused, not from the power of manipulating this man’s behavior but of the simple act of laying hands on his bare flesh.
S was also aroused, his erect penis sticking out of the bath water, the tip of a proverbial iceberg. Like the captain of the Titanic M knew it could cause her problems. She was scared of admitting she might want this man, might want to abandon all she had fantasized and hoped for. She was frightened of letting him fuck her and sinking the ship.
The apprehension became contagious. As M started to work on S’s make up he started to ask questions. She has previously insisted that his obedience meant absolute trust in whatever she wanted and planned, that knowing what might happen was unnecessary. In the mix of confused feelings and emotions M could not help but answer.
“If we are going out dressed as two women, are you planning we get picked up?” His voice sounded hesitant.
“I can’t control what other people will think and do,” M replied, equally nervous. “But given my experience of going out with girlfriends, I expect to attract some attention and I would not be surprised if people talk to us.”
“If they do, are you hoping to invite them back to the hotel with us?”
“That will depend.” While M might have admitted that the idea appealed to her, she was not prepared to get into a situation she could not control. She had experience of picking up strange men. She liked the uncertainty and to some extent, the risk and the danger but the circumstances were now very different.
“I will not let anyone harm you if that’s what you’re worried about,” she said reflecting on her own thoughts. “I would never let anyone hurt you.”
“Thank you.” The worry lines creasing S’s face eased slightly. “But if you did invite someone back it would probably be a man. Am I going to get fucked?”
It was one of those moments that caught M off guard. It was not that she hadn’t considered the possibility, or even fantasized about what it would be like to watch but the idea suddenly had a reality she had not expected. She again felt that rush of hormones through her veins, that flush of warmth that ran from her face right down to her groin.
“If I told you that is what I wanted,” M asked, trying hard to control her breathing, “that I wanted to see you taken by another man, that I wanted to watch you being fucked, would you do that for me?”
“I would do anything.”
M recognized the fear and trepidation in the man’s voice, but he had spoken without any hesitation. He had agreed obediently and the effect on how M felt was overwhelming. She unfastened and took off her robe, then removed her bra allowing her hardening nipples freedom, then her panties. It was the first time S had seen anything of her body let alone her naked form. He was entranced.
“May I masturbate?”
M nodded her agreement and watched as the man took his hard cock in his hand. It seemed far larger than any of the photo’s she had seen, the head engorged and swollen. S jerked himself vigorously as M felt her own juices dribbling down the inside of her thigh. Then he came, spraying cum over the desktop, the floor and his chest.
M indicated that S should go clean himself up as she quickly took herself to her own room and shut the door. The sight of his cock, the thought of having it inside her, of having that flood of semen washing through her womb, took her to the edge. The slightest touch of her fingers against her own hard clitoris sent her over the top. She came violently and loudly, a paroxysm that shook her body over and over.
M could easily have walked back into the other room and told S to fuck her, could have happily spent the rest of the day just experiencing the many things a man could do with his hands and cock, and while that may have satisfied both of them, she needed more. Now she had S ready to go out as a woman she had to see what other joys it might bring. The power had her. She knew this addiction had to be fed.
M quickly showered and slipped on her own yellow dress, underwear suddenly seeming superfluous. When she returned she found S fully clothed, adjusting his blonde wig in the mirror. The sight was breathtaking. He lacked the shape and stature to fool anyone into believing he was a woman, and despite the padding in the front of the basque remained flat chested, but he was beautiful. M added the final touches of make up. They were ready to go out into the world, both nervous of what lay ahead; the man of how people would react, the woman that this peak of excitement may soon end.
Dinner was everything M had hoped and planned. The staff were attentive, the food was exquisite and the atmosphere divine. There were passing glances from other patrons but the smiles seemed friendly. If there were comments made they were discreet enough to be unheard. The bar and night club however were a very different story.
M had expected a mix of men and women and hoped for some sort of interaction. She had not anticipated the larger groups of stag and hen parties, or that most of the people would be already drunk. What should have been flirtatious behavior bordered on aggressive. What should have been friendly banter was crude and unpleasant; she hated the term ‘dyke.’ When someone grabbed her breasts on the dance floor she knew they had to leave, but not before planting a stiletto heel firmly and heavily on the perpetrator's instep.
As the pair sat in the relative peace of the hotel bar sipping ridiculously named and priced cocktails, M felt deflated. Her experiment had worked and she knew she could live off the memories for a long time, but she had expected a more climactic end to the evening. S had confessed that he’d enjoyed every second. M was pleased but the words no longer carried that magic, the spell had been broken.
When M took herself off to the ladies she was joined by a younger woman, a pretty brunet dressed in blue jeans and dark green cashmere sweater. M noticed her beauty rather than the person. She certainly didn’t notice how the woman hovered, trying hard not to catch M’s glances in the mirror.
“May I ask you something?” The voice was young and soft and floated past M like a cool breeze.
“Of course,” M said instinctively.
“It’s just that Paul has been watching the two of you. He’s too shy to do anything about it, but he has the hots for your friend. Are you two a couple?”
“Not in the way you might imagine,” M said, hardly able to contain the smile. “I was thinking we’d order more drinks. I’d be more than thrilled if you’d join us.”
Over the course of the next two hours and more alcohol than was sensible, M learnt that their new friends shared a house and were at the hotel arranging an anniversary dinner for Paul’s grandparents. It soon became clear that Paul was gay; his mannerisms and attention to detail spoke volumes and he could hardly take his eyes off S. When Tonya confessed, amidst a fit of giggles, they had never bothered to repair the lock on the bathroom and often walked in on each-other naked, M guessed the woman may be similarly inclined. When M brushed her hand against a denim clad thigh to have it immediately clasped and held tight, she knew.
As the barman started to show signs he wanted to close up it seemed the most natural thing in the world that the four go upstairs. When M took a seat on the sofa Tonya sat on her lap, not questioning why they’d remained in S’s room. When S collapsed on the bed with Paul and looked to M for approval, she simply nodded.
Apart from the occasional distraction of kissing, Tonya and M watched as Paul and S slowly but methodically undress each other. They looked on while the two fondled and groped each other, and were entranced when play turned to mutual sucking. Only M could see the questions, how S looked at her. Only M knew the man was following her every command and when Paul showed signs of wanting to fuck, only M could tell the submission was hers to decide.
Anal sex was, for S, painful. He had admitted to using toys but had never had a real cock inside him, and from what M could see, Paul was well endowed. M could feel the hurt, could hear the intense gasps as his sphincter muscle was torn, could see the tension as Paul slid his penis deep. All the time their eyes locked. S was doing this for M. She was not a cruel woman, she would never knowingly inflict pain. She hoped that pleasing his mistress was enough.
Her concern over what was happening kept M in the room. Her arousal was at a peak, she desperately needed that climax. She wanted to discover what delights Tonya might offer, the young woman so lovingly curled up in her arms, but had to stay. She had to watch over S until his work was done.
Long after Paul and S had fucked each other senseless Tonya stood and announced she should get her flat mate home. M watched the woman glide across the room only to return and write a phone number on the inside of M’s arm. No words were exchanged, just the sweetest of smiles.
Alone, M helped S remove the last vestiges of clothing and make up and got him into bed. She undressed and climbed in beside him wanting to at least share the warmth and softness of her body. M would have allowed S to fuck her but with the smell of Tonya still in her nostrils, and the memory of her touch, she was not disappointed when S fell asleep.
M crept from the bed and dialed the number only to hear a phone ring in the adjacent room. She stepped through the door hardly caring what magic had made this vision of beauty re-appear. Tonya smiled from the bed with nothing but love and desire in her eyes then submitted willingly as M started to undress her, sliding the sweater over the woman’s head, revealing the most beautiful pert breasts. Slipping jeans over Tonya’s beautiful white thighs was a little more clumsy, but the first glimpse of purple satin panties pulled tight against the woman’s wet lips, equally enthralling.
It wasn’t long before both were embracing, fondling, kissing. M felt as if she had to experience every cell of this breathtaking body in fear it may vanish. She was hungry for every taste, every touch. She kissed Tonya in places she had never kissed any woman before, not wanting to miss any possible sensation.
M was aroused, more than she’d imagined possible. Watching S had been powerful and had her at the brink but this was different. As much as M wanted Tonya, it was clear that Tonya wanted M, but rather than control, rather than direct how their lovemaking played out, M wanted to just give in to all that was happening.
She found Tonya kissing and licking her, even sucking on her toes while massaging her feet. The woman placed her lips against M’s eyes ensuring they stayed shut, before placing the gentlest and most loving kiss on her mouth. M found the woman biting on her nipples, gripping and pulling with her teeth. M felt the woman’s fingers slide easily into her vagina and anus as if exploring how it feels for the first time, and when one finger wouldn’t go deep enough, it was replaced with two and then three.
M expected her orgasm to come quickly as they had previously but Tonya managed to keep her at that peak, manipulating her senses, carefully avoiding the things that would make her cum. M felt as though her heart would break under the strain. She imagined her lungs would fail to keep taking in enough oxygen when her breathing was so shallow. But still she lived, every nerve on fire.
When the climax did come, it started softly. M felt the first wave ripple through her body, followed by a second, more powerful than the first, then a third, They continued, each building on the one before, each getting stronger. M heard noises she didn’t recognize, deep guttural screams. She felt bodily fluid being squeezed out her vagina by each contraction, soaking the skin between her legs, running down the crease of her buttocks, forming a puddle on the bed sheets.
As M came, so Tonya moved to sit over her face. With her arms now pinned, M could only oblige this woman with her tongue and did so happily. She felt the tight puckered hole of Tonya’s ass, the smooth wet lips of her cunt, and finally the hard bud of her clitoris. M heard cries that were not her own. M for the first time ever felt another woman climax into her mouth.
Totally spent and exhausted, the two women collapsed into each other’s arms. After more soft kisses Tonya fell into a deep and contented sleep while M lay and relished the feel of the body laying next to her. M didn’t understand all the emotions flooding through her veins, she didn’t know she was falling in love. She only knew that for her, life was different.
