I. The Tomgirl
Monica has been eyeing Ash, one of the new cybersecurity officers that her university hired lately. He is quite a strange yet popular guy in his cosplay and anime circle. Ash is not an alpha male jock, quite the opposite in fact. He likes to wear girly clothes, even his working slacks have a feminine cut that makes him look like a petite slim young lady at first glance. He’s popular with a certain adventurous group of guys and girls that are into crossplay, or cosplaying a fictional character of a different gender. Girls like him as a fun way of exploring the other side of the pool so to speak while guys tend to request crossplay of characters that are too risque even for the most ardent female cosplayers. Oddly, he never escalates any dalliances into serious relationships. Perhaps he’s still not over spreading his wild oats on any field that he encounters.
She’s noted how different Ash’s appearance is to her loyal husband John. John is a down to earth office guy and loving father to their two young kids. He’s the rock that Monica has clung to through the years. Time just sculpted his handsome frame even better as he kept in shape to avoid heart complications that plagued his family.
Monica has thought about getting into an encounter with Ash for a long time. She has been loyal to John for the ten years that they are together and she thought one night of fun won’t hurt their relationship. In fact, he might just like to join the fun with Ash.
You see, Ash is as passionate about cybersecurity as much as his role playing hobby, due to how several of his cosplayer friends were attacked and stalked online. His mantra is “Trust but Verify” and is quite honest with his sexual partners. He ensures that he’s regularly tested and keeps condoms always at hand. This also extends to relationships as he will outright refuse any partner who is committed to or married to another person. Monica admired this trait of his and thought that he’s the safest pick for her night of fun. Too bad she has to give a little white lie to get him hooked.
One day she finally was able to talk to him alone after work. Monica wore a rather revealing top to enhance her bountiful breasts to help persuade him. Her pencil skirt was a few inches shorter than usual and it greatly accentuated her curves.
“Are you sure your husband is okay with this?” Ash asked as Monica moved a little bit too close.
Sure she’s years older than him but the sensation of having a professor seduce him is quite exciting.
“Of course he does!” Monica said, her tone almost betraying herself.
“He might even join us, wouldn’t that be fun?”
The last one was true. She intends to sample Ash and if she played her cards right, John might indeed join her in this spicy new adventure.
“Oh okay, maybe on the weekend Professor… I can arrange a hotel room for us.”
“Just call me Monica, dear…” she interrupted. “And a hotel room would be fine!” she added before walking away.
Ash nodded and smiled faintly and he bid the sultry wife goodbye. He’s never been to couples but since the wife and the husband are on board then I guess it won’t hurt to try a new experience.
Monica smiled to herself as Ash went home. She has caught her tomgirl.
II. The Weekend Trip
“Hi Honey!” Monica chirped as she planted a deep kiss in her husband’s lips.
It’s Friday night and her anticipation is killing her and she needs some of her sexual tension released.
“Woah! what’s gotten into you?” John said as he wrapped his arm around his wife’s waist. “Not that I don’t like it…”
She actually had several contingency plans in mind on how to get rid of her husband for the weekend and was pleasantly surprised when he told her about his fishing trip with the kids last Wednesday. She’ll be sure to be back home like nothing happened by the time they get back.
“Oh, nothing. The kids are asleep and you’ll be out with them on a weekend fishing trip” she said coyly, making circles on her husband’s buff chest.
“You know you can just join us, my folks would appreciate you helping handle those troublemakers. Besides, the weather tomorrow should be nice.”
“No, I really don’t like mosquito bites this time of year.”
“Last chance to have some family fun, you’ll regret it.” he said teasingly as held her close to his body.
“What if I give you a special treat tonight instead?” she winked as she held his hand and led him to bed.
That night Monica gave John a wild ride. Her husband was enjoying the show as she rode his dick, her auburn hair hiding her nipples every now and then. However, her mind is elsewhere as she imagined doing it with her new lover tomorrow.
III. The Hotel Room
“Okay Professor, I’m ready.” Ash said as he finished the touches on his swords-woman cosplay.
Monica was amazed at the details that the tomgirl put in his outfit and mannerism. Here he was, looking like a blonde medieval lady in a blue dress. He has the golden sword to go with the outfit in his bag but Monica decided that she doesn’t need that much detail so he just left it there. The professor wondered how he was able to make a convincing cleavage and pair of realistic, albeit rather flat, breasts but decided to ask him after doing the deed. She had seen this cosplay online and also its lewder version. There, she saw Ash showing his prominent ass to the camera with nothing but white panties and his wig. He was turned ever so slightly so that his chest remained hidden. A teasing arm is playing with a lacy bra which implies what he’s hiding. Had she not known his identity, she would rather be scandalized by the almost naked girl’s actions.
“Okay, now wear this blind fold.” Ash instructed. “It’s time to play!”
Monica eagerly wore the blindfold. She felt fingers gently tied her hands backward and the sound of chains.
“My, how kinky!” she said as said fingers led her to a room.
She heard the door slammed shut and locked. Then came the worrying sound of someone typing on a keyboard.
“Ash, what’s the meaning of this?” Monica worryingly said as she heard the sounds.
“Insurance, professor!” Ash said in an electronic voice. “You almost got me killed!”
“What?” came Monica’s startled reply.
“I went to check with your husband about this little adventure just to verify if he’s on board with this whole thing.” Ash continued. “He didn’t know and he almost choked me to death. I’m just glad that I’ve escaped with my life.”
“Wait, why would you do that?” Monica said, panic starting as she felt her skirt and shirt being ripped off of her body.
“Trust but verify, professor.” Ash said coldly as more keyboard tapping was heard in the distance. “It’s not just for couples you know.”
“No, please… I’m sorry. I’ll do anything!” Monica pleaded “I’ll even cover for you. John won’t hurt or contact you ever again. I swear! Just let me go.”
Monica heard more tapping at the keyboard which was followed by uncomfortable silence. Finally Ash talked after what seems to be hours.
“Fine… kneel and open your mouth!” Ash’s electronic voice boomed.
Monica did as she was told. Her bound arms made it difficult to balance but she managed to kneel.
“If you make me cum, I’ll let you go. But I’m keeping a video as insurance.” The voice continued.
The cheating wife felt a hot penis forced itself in her mouth so hard that she almost gagged. Still she pushed on, taking the cock deeper and deeper into her throat only letting it go so that she could take a breath. While not ministering the shaft, Monica nibbled at the hairy balls, giving them the same erotic treatment. There was a fury of typing again as she felt the cock convulse in her tongue. She expertly caught the tip and drank all of his load. Monica usually spit semen after blowing her husband but she thought that if she treated Ash nicely, she might be able to convince him to delete the video too. She can’t see the tomgirl but she tried her best to gulp down the baby batter and present her empty mouth for him to check.
“Very good professor!” Ash cooed tauntingly. “A deal’s a deal. Now pack your things and get out of here!”
She felt someone remove her chains and put a bathrobe to cover her nakedness. A set of fingers then guided her away from the room.
“You can remove the blindfold now.” Ash said.
She did so and saw Ash, still in his crossplay outfit but with a headset on, relaxing on the couch. An open laptop was placed on the coffee table in front of him.
So if he’s sitting there, then whose dick was she sucking back there?
“John!” she exclaimed as she turned around.
IV. A Little Talk
“You!” Monica stammered, her breathing heavy with anger against the relaxing tomgirl. “You are horrible mot-”
“OH PLEASE!” Ash interrupted loudly. His voice was strong and firm yet he did not stand up from the couch. “The alternative to this prank was way worse!”
“That’s true.” John said sadly. “Honey, you almost ruined our family.”
Monica stopped on her tracks and turned to her husband.
“Honey, look I’m sorry. I just wanted to have some fun.” Monica said to her husband apologetically. “I was sure to introduce you to Ash in the future.”
“I was ready to beat him up then and there. Then the whole university, no, the whole town would know about your affair and the three of us would be ruined.” John said, ignoring her wife’s apologies.
“That’s horrible, I swear I won’t do this again.” Monica said still looking very sorry about the whole thing. “I did not touch any other man before this. You’re the only one I love.” Monica then turned to Ash, he’s still mad but is otherwise silent. “I think I also owe you an apology.”
“Nah, we’re good.” Ash said dismissively. “Actually, your husband was very civil. I was just messing with ya back at the room.”
John then smiled as if remembering a half-hearted joke. “Well, when I yelled that he will not fuck you, he didn’t yell back or even taunted me. He just business-like asked if fondling is allowed and if penetrating my ass is still on the table. That was weird yet intriguing… So I let him explain what the hell is happening.”
“We hatched this prank to teach you a lesson, Monica.” Ash added, his scowl changing to a more relaxed laughter. “I’m sure John loves you very much but he also thinks that you should pay for your plans behind his back. Ya get what you deserve but not to the point that this will escalate faster AND we guys had some bit of fun.”
“The fishing trip was my idea to get you off guard and also as a final test to see if you’ll turn back.” John said. “The kids are having fun with my folks. I’m just glad that we pulled this prank well.”
Monica felt dumb, she is a very intelligent woman but she’s not good with all this cheating stuff. Maybe it’s not only men who thinks with their little head.
“But what about the video?” She asked.
“Oh that! Wait a bit.” Ash said as he removed a thumb drive from the laptop and handed it over to Monica. “I didn’t actually see what happened in that room. Anything sexual was all John.”
Ash turned the laptop screen towards the couple to show that the screen was just a messaging app. “John and I were communicating via chat. I actually have other acts in store for you but my accomplice back there can’t hold his cum.” He jokingly glared at John who just laughed it off.
“It didn’t feel like John’s, it was way larger than normal…” Monica protested.
“Too much information, woman!” Ash cringed.
“I have to admit.” John said. “That the whole you being bound in chains while wearing only lingerie was a great turn on. I’ve never been that aroused since our honeymoon!”
“Too much information, man!”
“Your blowjob skill was also amazing, like you are blowing me like your life depends on it.” John continued. “I have to warn Ash that I can’t stop myself from cumming.”
Monica looked at the small thumb drive which contains something that can break her family and career. She then gave it to John, knowing that she doesn’t have a say in the matter. Her husband took it and then promptly smashed it to bits to the relief of both Ash and his wife.
“What now?” John said.
“I had my pound of flesh.” Ash said as he carried his bag and headed towards the door. “What’s next is between the two of you.”
“So, a few beers after work this weekend?”
“Uh sure, as long as your wife’s fine with that or if she decides to hang out with us.”
“I’m sorry.” Monica said as she glanced back to her husband who was sitting next to her at the hotel room’s bed.
“It’s fine, honey.” John said soothingly as he held her close in his chest. “It’s all good.”
The couple cuddled this way for a little while until John broke the silence.
“So… uh do I get to fuck him? With you joining the fun of course.”
“What?” Monica said as she pulled away from her husband to see if he’s serious.
“I asked him if he’s still open about the whole thing if our plan went well.” John continued. “He’s still game as long as everything is above board.”
John handed Monica a piece of paper with Ash’s handwriting. It contains several sexual acts that he’s willing to do with the couple. Besides each act are two blank lines where she and John can give their consent. John then handed his wife a pen.
“Ash insisted that we do it this way since people might be able to hack this info if we did it electronically. You put your name on here and I’ll fill up mine on the things that I’m comfortable doing. Like this one.”
John pointed at the “butt stuff” option.
Monica looked at the paper and then back to her husband. Had she communicated her needs honestly, then they wouldn’t be in this mess. She was grateful that he’s as adventurous as he’s understanding.
“No honey,” Monica said as she handed the pen back to her husband. “You lead and I’ll follow.”