Author's Note: This is my first erotic story in this website. You're feedback and constructive criticisms are welcomed! Let me know if you want a sequel.
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.
