Cuckold Cheat

Part One

Chapter One

 

I met Tomassa at one of those horrible work-related conferences that no one wants to go to but the company dropped a ridiculous amount of money on the meeting, so everyone in the office had to go. I only half paid attention to the workshops. I’ll admit it. I was scanning the crowd for attractive and likely women. Tomassa was rather plain, but she had long, straight blonde hair and I couldn’t resist flirting with her. Maybe she was a few pounds overweight, but that would be overly critical and judgmental of me. It wasn’t as if I had a perfect body. Yes, I tried to stay in shape and work out, but I wasn’t gym obsessed.

Still, Tomassa played along when I approached her after one of the workshops. 

“That’s an unusual name,” I said pointing at the tag right above her breast.

Okay, sorry. I admit it. I aimed my finger more at her breast than her name. 

I can be an over ass more than I like to admit.

“My friends call me Tomi,” she replied.

“So...can I call you Tomi?” I asked.

She laughed.

It was that easy.

We sat next to each other at the terrible lunch that was served. It was edible, but just barely. 

We talked more than we ate. Half the conversation was about how terrible the food was.

“Want to cut out of here and get something decent to eat?” I asked her.

She looked around nervously. None of my coworkers were in my afternoon workshops. “Aren’t we supposed to stay the entire day.”

“I’d rather go home and get something good to eat.”

“How far is your place from here?” she asked.

Suburban sprawl is weird. It’s easier to measure distance is drive time as related to the time of day. “Right now? Fifteen minutes. After the workshops at five o’clock when everyone else leaves? Easily half an hour. Or more.”

She was reluctant. I could tell. Anyone could tell. But still she played along. “What do you have to eat at your place?”

“Mostly leftovers.”

She laughed again. “You know how to romance a girl.”

“I’m sure they’re delicious.” I got up from the table and headed to the exit. She caught up to me by the time I reached the door.

On the way out to the parking lot I gave her my address and she promised to follow behind in her car. 

My heart was thudding in my chest and I couldn’t believe my good luck. We kept things cool as we headed to our cars. We weren’t leaving a club where you were supposed to hook up with strangers. I saw her just as she got into her Honda Civic. Her face was flushed as if she were blushing.

I hoped that was a good sign.

I didn’t live in some super-exclusive place. I rented a place in a garden apartment complex. It was nice but not fancy. Tomi didn’t comment on it at all as we went into my place.

“So...what do you have to eat?” she asked as she looked around my rather plain apartment. The living room was little more than a nice couch, huge television, and every gaming system known to man. I’m sure it didn’t impress her. I didn’t care.

“I was hoping you’d supply that,” I said, moving too close to her.

She went back one step, pressing her back against the wall, but she didn’t look afraid and she didn’t protest. 

When I ducked my head to kiss her, she lifted her chin so that our lips met. 

The kiss was intense. 

She willingly accepted my tongue into her mouth. I sparred with her tongue and stroked the inside of her cheek for a little preview of what she had below.

I don’t know which of us broke the kiss, but when we both stopped for a breath of air and a moment’s reflection, she looked me right in the eyes. “You want me to supply the food?” Clearly she was bewildered by me. I didn’t blame her.

“Uh-huh,” I said before sliding down her body, lading on my knees in front of her. 

Tomi, like myself, was dressed casually because that’s what conference day was all about. She had a thick black belt that cinched her jeans tightly around her waist. The button-up blouse she wore did a terrible job of hiding her large tits. I hoped that was intentional. 

I ran my hands down her hips and to her thighs, feeling the soft flesh underneath the denim. I fantasized a minute about what her skin would feel like and then I moved on to find out exactly what it felt like. I fumbled a moment with her belt and she took over to loosen it. I helpfully popped the button open and unzipped her jeans.

“I’m sorry I’m so fat,” she apologized.

I hated her for just a second when she said that. She was looking down at me with her round face that was flushed red with embarrassment, or maybe with lust. Her blond hair perfectly framed it. Yes, she wasn’t perfectly proportioned with a model’s body, but that didn’t make her any less sexy to me. 

“Don’t say that,” I told her. “You’re beautiful.” I wondered if she had Polish ancestry with her hair and face. Maybe Danish. It didn’t matter. I wiggled her jeans over her hips. Yes, she was a little fleshy, but I loved that and kissed her tummy right above her cotton panties that were decorated with sheep. I glanced up at her questioning her sartorial choice. 

“I wasn’t planning on getting laid today,” she explained.

“They’re cute,” I commented before pressing my face into her crotch. I could smell her pussy. She was clearly aroused and I grabbed the elastic band of her underwear between my teeth. It was an ineffective way of stripping her, but I hoped it showed that I was playful as well.

“Fuck,” she cursed.

I wasn’t sure if she was worried or eager.

“Problem?” I asked.

“It’s been a while since I’ve...since I’ve had sex with someone.”

“Do you not want to?”

“Hell no,” she declared and yanked her blouse up over her body.

I was right. She had huge tits. They were barely contained by her bright pink bra that didn’t match her panties. Still pressed against the wall, Tomi kicked off her shoes and I yanked her jeans all the way off, leaving her in just her undergarments. 

My cock was hard and uncomfortable in my jeans. I wanted to go down on her to taste her pussy before we went any further. That was the way I judged women: by how their pussies tasted. 

I’m sure there are worse ways to judge. 

Before I could press close again and ease her panties down, she tugged at my shoulders, trying to get my shirt off. I helped her and pulled it off, tossing it aside.

“Stand up,” she said. “I want to see what you look like.”

“Really?” I asked, getting back to my feet, but taking the opportunity to get my sneakers off, stepping on their backs to expedite the process.

“I’m not going to fuck you unless I like what I see.”

That was a reasonable request and I unbuckled my jeans, opening them up, before pushing them down. Just like that I was naked in front of her. My hard cock bobbed around a little while I stepped clear of my jeans. I felt a little foolish in just my socks, but I’d take care of that soon enough.

“Wow,” she said, reaching out for my cock. She gently ran her fingers up from my balls that were tight against my body, up along the shaft, all the way to the head that was just starting to leak some precum. Circling the head with one finger she let her hand slid back down a bit to lightly grip my shaft. 

I shivered at her control.

“I like your cock,” she complimented me.

“Thank you.”

Her fingers curled around me and slowly went up and down. She wasn’t masturbating me like I would do myself, but that was the point. Tomi wasn’t trying to get me off; she was trying to tease me.

It was working.

“Is this too forward?” she asked.

“No...it’s perfect.” I closed my eyes and let her manipulate me for a minute, but then I grabbed her wrist and stopped her. “Except I don’t want to cum that way.” 

“Do you want to fuck me?”

I opened my eyes. “Yes.”

“Here?” she asked looking around the living room.

“Bedroom.” I took her hand off my cock and started to lead her through the apartment. It wasn’t that big. It didn’t take long. My bed was a mess but I didn’t care and she didn’t comment. Only when we were in my bedroom did I notice the ring that pierced her belly button. There was a small charm dangling from it.

Tomi didn’t protest when I moved her onto the bed, shoving the sheets and blankets aside. She was on her back and I was on top of her. We kissed for a minute, my hard cock pressing on her thigh before I started kissing my way down her neck. I planted a bunch of kissed in her cleavage, but I didn’t remove her bra, not yet. It was still too soon.

With more kisses I worked my way down her body, briefly tonguing her belly button and the little ring and charm which made her gasp, before I stopped at the edge of her sheep-covered panties. 

This time I used my hands to pull them down her hips and legs.

She helped.

Her skin was perfectly smooth and pale except for her shoulders and chest which were generously covered with freckles. It was still early spring. Her body was still white from having been hidden from the sun all winter. There were faint red marks on her hips where her underwear, just a little too small, cut into her skin. 

Between her legs she had shaped her pubic hair into a neat strip, a couple of inches wide. For a woman claiming that she hadn’t had sex in...a few weeks? Months? A year? I didn’t know. For a woman claiming a lack of sex, her pussy was well-groomed. I kissed above her mound and then to the side. She didn’t shave. It was perfectly smooth. Maybe she waxed or had it laser removed.

Just that little detail let me know she took some pride in her body and was a sexual woman.

That was perfect. 

I pushed her legs apart and her scent rose up from her pussy. Running my tongue through the blonde curls, I found the top of her slit and then her clit. 

My cock throbbed when she gasped at the touch. I wiggled my tongue against the tiny bit of flesh and she tensed up, squeezing her pillowy thighs against me.

“Should I stop?” I asked her.

Her eyes were clamped tightly shut. “Nooo,” she moaned.

I moved my tongue lower, into her pussy. She was wet. She was tart and sweet and musky all at the same time. The inside of her tunnel was as smooth as the inside of her mouth.

Her knees went up toward the ceiling, giving me better access to her pussy.

“Can you cum from oral?” I asked her, taking a quick break.

She answered me by enthusiastically nodding her head. I traveled back up to her clit and got to work on it. I sucked. I licked. I slipped a pair of fingers into her pussy and stroked the front wall searching for her little hidden spot behind the pubic bone.

Tomi was a very sexual woman. I brought my best game to her pussy and it only took a couple of minutes before she was gasping for air. When I sucked hard on her clit she pounded the mattress with her fists before her entire body shook and a little trickle of her natural juices filled my mouth.

It was only polite to swallow.

Pulling my face up from her pussy I smiled at her. “Did you cum?” It was a cliché question, but I wanted to ask it because I knew I had made her cum. Unless, of course, she was the best actress I’d ever been with or seen.

I’ve seen a lot of porn.

“Fuck yes,” she answered. “Are you going to use your cock on me?”

I knelt up and moved to the side of the bed. I was good and hard. She was wet and panting to be penetrated. “Yes. Just let me get a condom.” I opened the drawer next to my bed and got one out.

“You don’t have to use one. I’m safe,” she said as I rolled it on.

“Better safe than sorry,” I said as I got back into position. Her hand went right to my cock and guided me in.

I had no regrets about fucking her or going down on her.

There are lies and then there are lies. Lies of omission aren’t as bad of a lie, but that’s my opinion.

And what’s cheating really? Looking at another person’s body? Flirting? Kissing? Mutual masturbation? Oral sex? Penetrative sex with a condom? Penetrative sex without a condom?

Pick a line. Wherever you put the line, someone has cheated.

Once I was inside Tomi, I realized that not only did her pussy look perfect and taste perfect, but it felt perfect to my cock.

It might have felt better than my girlfriend’s pussy. Or maybe it was the thrill of fucking someone new for the first time combined with cheating. Either way, the sex was, to use the cliché, fan-fucking-tastic. I didn’t regret fucking her at all. 

I don’t want to brag, but I’ll do it a little. I made her cum twice before I finished. Once on her back and once doggy style. She didn’t seem to have a preference for which position she came in. I liked seeing the full flare of her ass when we fucked doggy, but it was just was satisfying to kiss her while we did it in the traditional missionary. 

Maybe she peaked a final time when I finished inside her, but I’m sure that was just my imagination.

I didn’t pass out and neither did she, but we faded into that hazy afterglow that accompanies amazing sex. I wasn’t sure how long we half-slept there in my bed.

I can tell you, however, precisely when I was awoken from dozing. 4: 37pm. It was the exact time my girlfriend walked into the bedroom of my apartment. She had the right. We’d been dating six months and she had the spare key. She almost always stopped at my place after work because I lived alone and she had two roommates in her bigger and nice place, but mine had privacy.

Except for when I had a guest over.

This was the first time I had a guest over that I had been fucking.

Did you forget that this was a story about cheating? I hope not because there’s going to be a whole lot more cheating going on before we get to the end.

Her first words at catching me in bed with another woman?

“Really Travis? You couldn’t go to her place?”

I sat bolt upright and Tomi clutched the sheets to her chest, hiding her tits. “Uh...here was closer?” I had no idea if that was true or not, but I felt the need to say something, even as stupid as it was.

Perrin ignored my stupid remark and looked at Tomi. “Get your clothes on and get out. I need to speak with my...boyfriend.”

With those words she turned on her heel and left the bedroom, politely closing the door behind her.

“Oh fuck, oh shit,” Tomi cursed. “What are we going to do?” She was in full panic mode. I didn’t blame her. I wasn’t sure if Perrin’s cool was worse than if she had turned into a raging maniac. 

“We’re going to get dressed and you’re going to leave,” I said as calmly as possible. I tried to make it seem like I did this all the time. I didn’t. It was the first time I had cheated on my girlfriend.

Technically it wasn’t cheating, but still…

Tomi jumped out of bed and grabbed her bra and underwear. Her fingers were trembling as she tried to hook the bra together. I helped her. It was the gentlemanly thing to do. I grabbed a pair of shorts and a t-shirt, putting them on as she cast her eyes around the messy bedroom. Her eyes were wide and fearful when she saw that I was dressed. 

“I left the rest of my clothes out in the living room!”

“Well, let’s go get them,” I said, heading for the door.

She stopped me, putting her hand on top of mine as I grasped the doorknob. “I can’t go out there naked like this!”

“You’re not naked,” I said with a calmness I didn’t feel.

“In my underwear!”

“Just pretend you’re wearing a swimsuit. A bikini.”

“That doesn’t help! Go get my clothes and bring them in to me!” She was trembling with fear and I felt bad for her. I sighed.

“Fine.”

Out in the apartment proper Perrin was sitting at the table that occupied the space between the living room and the kitchen. She had poured herself a drink and was calmly sipping from it while scrolling through her phone.

I couldn’t meet her gaze.

I grabbed the pile of clothes that Tomi and I left behind and quickly returned to the bedroom. Tomi grabbed them from me and quickly finished dressing while I watched her. It was disappointing because she had a lovely, curvy body and I was reasonably certain I would never get to see it again, let alone fuck her.

I tried anyway.

“Can I get your phone number?” I asked as she stepped into her shoes. 

“Are you fucking crazy?!” She glared at me. “Your girlfriend is out there!”

I shrugged. “She might not be my girlfriend for much longer.”

Tomi rolled her eyes at me. It was expected. “You are fucking crazy,” she declared and made a dash from the bedroom to the front door, mumbling, “Sorry,” to Perrin as she left.

Perrin said nothing but did look up when I appeared.

“Did you use a condom?” she asked me, putting down her phone.

“Yes.”

I couldn’t read her expression. “That’s good.”

Before an argument could start I blurted out, “You always said we had an open relationship!”

“Go get it,” she said to me, ignoring my protest and attempt at circumventing any discomfort that we were both in for.

“Are you...are you serious?”

She gave me a look. I was certain that Perrin loved me and was open-minded, but this was a big step.

For the both of us.

“Go get it,” she repeated. “We both agreed to this. You’re the one who made the mistake.”

Did I actually make a mistake or were my actions subconsciously intentional? There was no easy answer to that question so I did what she asked. 

What she wanted was in the bottom drawer of my dresser in a black velvet bag closed tightly with a drawstring. It was surprisingly light but solid. I brought it out to Perrin.

She smiled when I handed it over to her. “This was your idea,” she reminded me as she opened the strings.

“Yeah but...fantasy is different from reality.”

“You’ve worn it before,” she said and shook out the elegantly shaped metal cage into her hand.

“But...only for short periods. For fun.”

“You won’t have it on forever. And this is for fun.”

For you, maybe, I thought to myself. “How...how long?”

“Get your cock out,” she said as she inserted one of the keys into the lock and opened up the device. It separated into two pieces plus the lock. I had worn it before, but only when we were playing around in the bedroom. Only for a few hours at most. Now...now Perrin wanted to make it permanent.

Well,...almost permanent.

I did what she asked, unzipping my shorts and pulling out my soft cock. It seemed smaller than usual. It was cool in the well air-conditioned room, but maybe I was just worrying unnecessarily.

Perrin frowned at my manhood. “Yeah, maybe you’d better take a shower first, “ she suggested. “And trim back your hair. Nice and short.”

“Should I shave?” I asked her.

“No. Not yet.”

I went to the shower and removed any traces of Tomi from by body. Her scent was replaced by soap and shampoo. I had an electric hair trimmer in the bathroom that I occasionally used on my hair when I wanted a quick buzz cut. This time I used them on my pubes, reducing the length of my short and curlies to almost nothing.