The Stylist | 2016

No one will ever confuse me with Channing Tatum, but I’ve always been a physically active person, thin, and generally dated women who were the same. I never thought that I would be attracted to a woman who didn’t have most or all of the features associated with conventional beauty. My perspective was recently changed.

I graduated college this year and moved to a larger city for the first time in my life. This was exciting because I grew up, even went to college, in the same small town where everyone knew everyone and people started settling down into domestic life in their early 20s.

On the way home from class one afternoon, I passed a salon. I generally don’t want to pay a great deal to get my hair cut, but I needed it, so I stopped there and asked if they had anything available at the moment. As luck would have it, they did.

The receptionist summoned “Mandy.” Mandy was one of those girls who, in high school, I would have dismissively thought of as having a “pretty face”, “but fat.” Mandy indeed had pretty face, with warm, bright brown eyes and a pallid, but even and smooth complexion. Her wavy, black hair hung slightly past her shoulders. Yes, she was overweight. That was immediately apparent. But, her neck seemed elegant nonetheless. Her additional weight seemed to compliment the curves of breasts, hips and butt rather than to conceal them.

“I’m Mandy.” she said as she extended her hand.

“Tyler, nice to meet you.” I replied and shook her hand.

She took me back to her chair where she did some work with clippers. We had a casual, pleasant conversation. She told me about her favorite restaurants and bars in the city and recommended some things to do around town. Nothing struck me as unusual until she led me back to the sinks to shampoo my hair. What about happened next can’t easily be explained with words. This generally isn’t a sexual experience, but way she worked her fingers through my hair and against my scalp was almost orgasmic. It wasn’t long before I had a raging hard on and had to put my mind elsewhere to let it subside before I had to stand up again.

She took me back to her chair, finished cutting my hair and we talked throughout. There was no flirtation, though, just friendly chat. She was soon done, I paid, tipped her and left. As pleasant as the experience was, I didn’t think about it again until she saw me shopping at a nearby grocery store a few days later.

We had pleasant, but still superficial conversation as we walked around, gathering the items we needed.

“So, got any big plans for this Saturday night?” Mandy asked.

“Nope, probably just pizza, football and beer. I don’t really know anyone yet.” I answered.

“Oh, you don’t need to spend Saturday night alone. I live right off Dresden, and I don’t like cooking for one, anyway.”

I was slightly surprised by the forwardness, but not entirely, so I agreed.

That night, she was wearing jeans and a simple, white v-neck shirt that accentuated her ample breasts perfectly. Her ass wasn’t just wide, as is the case with some women carrying a few extra pounds; it was round, too. It looked as if it were going burst through her jeans. I knew then I had to have her.

Nothing happened at first. We had a surprisingly good dinner of Italian herb grilled chicken and pasta, not to mention our fair share of wine. After dinner, we sat her on couch, drank more wine, and began to flirt a bit.

It didn’t start quite how I thought it would, or quite like any other hookup in the past. The tension wasn’t broken when we both looked into each other’s eyes and locked lips. I was watching TV when I felt her begin to nibble softly on the bottom of my earlobe and felt her place her hand on my knee. Normally, I would have turned to kiss her, but there was something so sensual about what she was doing. I liked it, and I think she did, too.

Mandy began to move her hand from my knee up my thigh at an agonizingly slow pace. She placed the tip of her tongue right on the spot where the collar bone meets the neck and continued back upward. Goosebumps popped up on that side of my body. Finally, I felt her hand reach my now rock-hard dick. Some women will grab too hard and too aggressively. Some don’t seem to know what to do at all. Mandy lovingly massaged it through my hands, applying just the right amount of pressure, releasing, and squeezing again.

I sighed up and involuntarily jumped a little at the pleasure.

“Yeah, that’s right.” she whispered into my ear, and then nibbled on the bottom.

She then effortlessly pivoted and straddled me. We began to kiss, passionately. Her massive breasts pressed against my chest and I reached down pull off her shirt. When it was off, she unclasped her bra, letting her beautiful tits fall free.

Her breasts were amazingly firm. No, they weren’t the perfect specimens one could see in a men’s magazine but they were beautiful. Her nipples were large and hard, perhaps slightly larger than the tip of your index finger. They were an average shade of pink and pointed upward ever so slightly. I wouldn’t notice the latter until I had spent more time with them. Her areolas were substantial, with numerous goosebumps.

I took them into my mouth and began to suck immediately. I knew that I should start soft, then go harder, but I couldn’t help myself. I felt her nipples become as hard as iron on my tongue and between my lips. Mandy reached down and began trying to unzip and unbutton my pants. I gave her an assist and then lifted my hips so she could get them all the way off.

She then lifted herself up onto her knees so that she was straddling me, reached one hand behind my hair, grasping a chunk of hair and bringing my mouth back to her eager nipples. With the other, she reached behind my back and began to caress my penis.

I shuddered again when I felt her hand touch it. What she did was so simple, but felt so good. She ran her finger tips up and down and around my dick, so softly that they were barely touching it. Then, at just the right moment, she grasped a little harder, forming a ring with her thumb, index and middle finger, sliding it up and down the length of my shaft.

“You are so fucking hard.” she quietly cooed in her soft voice. “So. Fucking. Hard” as if each word was its own paragraph. Then, just went I thought her stroking may bring me to orgasm, she’d slow down again.

I grabbed her hips and rolled her off me. I unfastened her jeans pulled them off as fast as I could. I like to consider myself a considerate and patient lover. One who loves foreplay and giving pleasure as much as receiving it. Here, I would usually kiss and lick her clit for a generous period of time until she was soaking wet, squirming and moaning with delight.

“God, I want to fuck you so bad.” I said instead, as her as her jeans fell to the floor. She didn’t say anything, but reached down, grabbed me to pull me toward her signaling she had the same thing in mind.

I did.

Her pussy was warm – almost hot -, wet, and welcoming. The length of my dick slid without protest into her and we both moaned from pleasure. I could feel her vagina pulsing, the walls contracting and relaxing. I swear, I could have just sat there motionless and came from that alone.

I began to thrust in and out of her, trying to not go too hard and fast at first because I didn’t want to cum yet. Each of her legs were over my shoulders, her hips elevated slightly. I was in a semi-standing position that was not at all comfortable, but I felt too good to care about that now.

I quickly felt myself approaching the point of no return. Her soft, squeezing pussy was proving too much for me to handle. I removed my dick and rubbed the shaft up and down her clit, something I’ve found most women loved, and Mandy did too. But, not right now.

“No, I want your dick back in me.” she said, reaching between her legs and putting me back into her pussy.

“But, I’m gonna cum if I don’t-“ I tried to protest.

“I don’t care. We’ll fuck again later.”

I tried to hold back, think of something else, anything, to last a bit longer. That was successful for about 30 seconds, then I couldn’t hold back.

“I’m gonna-“ I announced.

“Let me jack you off, please. I wanna to make you cum.” Mandy said, in almost pleading manner, that was itself almost sexy enough push me over the edge.

I did, and I took my penis out of her vagina, she quickly knelt before me. One hand gripped the base of my dick, and she made a tight ring with her fingers as she had done before and began to stroke. Again, hard, but not too hard. Fast, but not too fast.

Soon, I exploded all over her. Cum flew everywhere. Some hit her cheeks, her lips, neck, chest. Some missed her entirely, hitting the couch behind us. Thick droplets of cum dribbled down her breast and onto her nipple.

“Goddamn!” I gasped, exasperated and absolutely pleased.

“That was fun!” Mandy said, now sounding more like a teenage girl than grown woman. “This should be a regular thing, don’t you think?”

“Oh, hell yes.”

And it was, and is. Mandy and I currently enjoy a casual friends with benefits type relationship, and we’ve had many delightful escapades since that first one the night she invited me over for dinner.