Jayro Cerqueira da Silva — Photography

Rear Entry with Style

A stylish way in

I knew Rebecca wasn’t like any other girl I had ever met before. I ran into her at a few business-related events, and she was always dressed with effortless elegance. She seems so exquisite; I was almost frightened to talk to her, as I feared it would shatter my illusion of what she was.

I guess that’s why they invented alcohol, as after a few glasses of champagne, one is almost always ready to do anything.

“This is a good place for a classy woman like you to be hanging out in,” I said, expecting a good response, but instead I got was a flat-out rejection.

“Sorry, come back to me when you’re a little more sober,” she said to me.

“I’m not that drunk, come on, at least let’s have a conversation.”

“I’m over this already. Come back another time.”

I knew a woman like that wasn’t going to be very easy. Most of the girls I have been with put out on a first date or even the first meeting. I’d wine and dine then and then 69 them and put my cock in their pussies. It was normally unprotected sex, as they thought that I should be given the ultimate treat for even approaching them in the first place.

None of them, however, were as attractive as Rebecca was. I’d seen her in short skirts, catching glimpses of the tattoos on her legs, which added to the curves of her body, especially the ones leading up towards her ass.

So, I made my retreat, and a couple of my work colleagues had a chuckle at me.

“There’s no way you can make it with her; she’s an impossible fuck,” Mark said to me.

“I understand what you’re saying, but I’m going to fuck that woman sooner or later. She can’t hide how she feels about me. I know that she’s covering it up with that attitude.”

“Are you even sure she likes men?” Mark said to me, laughing as he drank champagne.

I was embarrassed for the rest of the night. I later saw Mark go with a fatter slut that had been eyeing him up all night. At least he got laid, I thought to myself. Maybe I should go with one of the other ones? They weren’t as nice as Rebecca was, but at least I’d be actually having a fuck. And who knows, their pussy might be really tight and wet.

Instead, I took my phone out and pretended I was looking at it. I snapped a few pictures of Rebecca, even taking a video of her as she danced around a little bit towards the end of the night.

I don’t normally choke my chicken, but that night I did, and I had some good visuals for it.

It was a couple of months later that I saw Rebecca again. I was at a wine bar that I often went to after signing new clients. We’re having a good time sharing some expensive wine courtesy of the company’s money when I saw Rebecca across the room. By the looks of things, she had been drinking, so there was an opportunity to approach her.

Once again, I couldn’t control myself and excused myself from my group and went over to where she sat at a table with one of her friends.

“Fancy meeting you again. Seems you have a refined taste for the finer things.”

“Yes, I’m not cheap. I wouldn’t be seen anywhere where a drink costs less than $50 a glass.” She gave me a brooding look.

“Yeah, I’m not a cheapskate, but 250 dollars for a bottle of wine is more than most people spend on alcohol in a week. I’m glad I have a company credit card.”

“I know it’s a little outrageous, but that makes me feel better than most people. I like the finer things in life,” she whispered in my ear.

“Why do you date male models or something? I thought those guys were all gay anyway.” I tried to make her laugh, but failed.

“For me, it comes down to cock size. It’s the 1% category that I’m after.”

My own dick wasn’t massive infact it was a little undersized. Then I thought most men lied about the length of their cocks anyway.

“It’s more to do with the motion of the ocean,” I replied.

“For regular people, maybe. However, I like a man who has a decent-sized cock. I can’t really feel anything if it’s shorter than 8 inches.”

I knew she could probably tell by the look on my face that I wasn’t packing anything that large. But I knew women often mock men about the size of their dick, but at the end of it, they didn’t really care too much about it.

“I guess if there’s a will, there’s a way for anything to work,” I said.

“Says the man who has a small dick,” Rebecca gave me a sly wink.

“To tell you the truth, I don’t have a big cock, but I do have a hefty wallet, and that actually means more in today’s society than anything else.”

“I guess that’s true, but if that were completely the case, you would be spending your own money, not you companies money, on your drinks tonight,” she scoffed.

“Well, I’ve made my business $1,000,000 today, so I think a few 100 on wine is warranted,” I countered.

“He made $1,000,000 today,” her friend whispered to Rebecca, but I had heard it. That comment had changed the tone of the conversation.

“I knew you were good, but I didn’t know you were that good,” Rebecca said. “I’m also professional with everything I do.”

“I didn’t see you leaving the party with any woman a few months ago?” She added.

“I wasn’t really interested in any of the normal women. I wanted someone exceptional.” I touched her arm, and that brought a smile to her face.

“I could tell. That’s why you were photographing my ass,” she said condescendingly. “ I bet you had a good wank that night.”

“A woman after my own heart,” I grinned. “How about I take you somewhere you’ve never been before?”

“But I thought you had clients,” she said to me.

“I think we’re just about done,” I said. I’d just ordered another bottle, and it had turned up, and they were already drunk; they didn’t even realise that I was gone or even there.

“There are a few single men there I think your friend might be interested in, so it’s a win-win for everyone.”

“But didn’t you understand what I said about big cocks?” Rebecca’s eyebrow raised suggestively.

“We’ll worry about that later. A classy woman like you needs to be wooed a little bit,” I said, locking eyes with her.

“Yeah, you’re right about that. I’m not easy, and I’ll make it extremely difficult for you, as I know you probably have got a small one.”

“You never know; it could be better in some areas where a larger one struggles.” I shrugged

“We’ll get to that later. I want to be entertained first.” She agreed.

We left the wine bar, and I took her to a rooftop bar just down the road, where we had a few drinks. She appreciated the skyline and purred at the price of the drinks that were extraordinarily expensive.

That wasn’t enough, so I got a taxi, and we went to a bridge where I knew there was a good view. I snuck out with a bottle of wine from the rooftop bar, and we drank it there and looked at the view of the city below us.

We talked for a few hours, and the alcohol and the conversation were obviously to her liking.

I pressed my lips to hers at an opportune moment, and she responded with her own. I was expecting some bad breath from all the wine to have drunk him but her lips tasted of lip gloss, and her perfume was intoxicating.

It got quite full-on as we felt each other’s bodies. She had it quite a sexy build, I could feel it under her dress. Her tits were full of silicone, and her ass was to die for, perfectly smooth and firm to the touch.

From there it was a quick uber ride to the hotel that I had booked before we left. It was a penthouse suite, approximately 1000 a night. Rebecca was impressed with the multiple bedroom choices as she explored the place.

We both had a shower and came out at the same time, and slowly we embraced again, and through the natural friction of our bodies, the towels dropped to the floor. I could see her pussy was aroused, even pulsating wanting to be fucked while her nipples were erect.

I appreciated what she looked like, but she looked down at my body, I didn’t even have an erection, despite having a gorgeous woman in front of me.

“It isn’t very big, is it?” She said to me, obviously disappointed. “It’s a pity because the night was going so well, but I guess we can try something.”

“I’m sure it can get bigger,” I said as we got into bed.

She worked her tongue on my dick, and it was like magic as it slowly but surely grew into a big and strong erection.

“That’s a good start,” Rebecca said as she got onto all fours and told me to pick a hole.

Her ass was beautiful, puckered up and tight. I spat on my Dick and put it in. “My favourite,” she said. “How did you know?”

“There are some places where a smaller one is better than a bigger one,” I said, doing it nice and deep.

“Gives me a chance to flick my bean a little,” she said, turning her head and then giving me a wink.

The realisation that she was a woman who liked to masturbate was a revelation to me.

“I see you are as fucked up as I am. Surely you have the vibrator you can use to get off with?”

With me still inside, she moved a little bit so she could pull out her vibrator from a drawer.

She put it on her clit at first and then inserted into pussy I could feel the device through the skin of her ass.

“Keep on fucking me,” Rebecca said. She rubbed the cream that frothed from her pussy and spread it on my dick.

“It’s fucking tight,” I said, perving at her tattoos that went up her legs to her ass.

I slapped her butt a few times, and noticed she was pulsating, almost choking at the mouth, as she was cumming like a virgin.

“Fuck this is better than any big cock I’ve ever had,” she said.

The vibrator was massaging my dick, and I could only grunt back.

“I know I seem like a sophisticated woman, but I love a penis in my ass.”

I pulled my Dick out, and she rolled around, and opened her legs wide. “It’s a beautiful looking pussy, and it’s nicely stretched out from the vibrator,” I commented

With no ceremony, I put it into her pussy and start fucking as roughly as I could.

While I did that, she slipped her cum covered vibrator into her asshole and started fucking herself.

“I’m going to cum,” I said.

She pinched the base of my cocks to stop me from ejaculating.

The horny bitch wanted to cum again, and I had to delay my orgasm because of it.

“Be a fucking gentleman,” she told me, her voice sounding like a dirty slut.

I continued up to the point where she started squirting all over my dick, so I pulled it out so she could watch me wank. At the same time, took her hand off my cock and egged me on.

I started decorating her pussy and stomach, which also had tattoos all over it. We watched with delight as squirt after squirt came out of my dick, and each one was more pleasurable than the last.

“I thought you were an elegant, classy lady, but it looks like you’re as deviant as I am.”

She loved that comment and told me: “This is just the start.”

Rebecca reached for my cock again, which grew rigid with her touch.

I’d underestimated the woman, and now she had me exactly where she wanted.