Fantasy Vs. Reality

My wife of 11 years had a very close friend that was all I had ever hoped to spend a few hours with alone. Vivian was, and still is, a beauty. She was physically fit, tall as well as leggy and flexible as all hell and still teaching gymnastics. My ex had none of those traits. Although for 7 years we had an adequate sex life I would not call it stellar, and it became very monotonous. I had always fantasized about other women as I had sex with my wife, who had become so unimaginative. Sex meant spreading her legs and letting me put it in her. I will admit that I had a healthy amount of “Vivian” scenarios in my inventory. As our marriage disintegrated in other ways, sex was the first to go. Vivian continued to spend time with my wife and I, and we would go out as a threesome or foursome with her husband to dinners frequently. Of course, my wife was trying to get her to take her side in our marriage woes until one day Vivian stood up and told my wife that our problems were not open for discussion, that she and Jerrimy were having problems as well. He wanted nothing to do with having “rug rats” and she was wanting him to impregnate her. Thus, he became impotent unless he had it in a condom. “I want so start a family, but he can’t fuck me without a condom.”

That ignited a desire to impregnate her in my mind.  

That night as I slept in the spare room, I focused all my fantasy thoughts on how it would be to have sex with Vivian. Light enough to carry around, flexible enough to fold up and drive into her camel toe, the one that always showed through her yoga pants. I wanted to make her firm little breasts jiggle and bite her erect nipples. I bet she was a screamer…Yes baby here it is, take my load deep into your fertile cunt. God I think I even moaned a bit myself as I had my first orgasm in a long time. 

A year later my divorce was final. The ex was still in contact with Vivian, and I guess they were crying on each other’s shoulders. I was a free man and trying to get back into the social scene as a 29-year-old that had married way too early. I, like many others, had confused sex with love and the fact that the ex had put out on the first date had my 17-year-old brain screwed up.

I had taken a small apartment up-town on the second floor, and I would see them occasionally. Masturbation was getting very old by now, so I decided to go out and look to see what was shaking in the area bars. I started with a sports bar, the least likely to find a woman in, as a warmup.

As I was reaching the bottom of my first scotch a hand slid onto my shoulder. “What’s a guy like you doing in a place like this?” Vivian whispered in my ear. I choked on my scotch like a fool, eliciting a cute laugh from her as she slid into the next stool. The bartender came over to see what was up. 

“Two of what he’s having,” she said as I recovered. There was enough light from the huge bank of TV’s to see that Vivian was dressed in a black body stocking. After some chit-chatting her leg pressed into my thigh. That was all the signal I needed as I ran my hand up to the promised land, where it met no resistance from her, other than to clamp it there with her other leg. It was apparent what was going to happen and that there was no need to be coy or superficial. “Vivian, I have jacked off a hundred times thinking of fucking and impregnating you.” 

“Is that so? I am honored.” 

“Yes.”

“Was I good?”

“Always a great finish.”

“Well let’s go, I think we have more important things to do than talk.”

“My place is two blocks from here. Shall we go?” I said as I downed the last of my drink and paid the tab. Vivian was looking in her little black clutch bag, found what she was looking for and smiled. We left holding hands and that shifted to me wrapping my arm around her tiny waist feeling her hips sway with each step. Walking slowly, I moved my hand up to fondle that firm breast. I was as hard as a rock and she grabbed it, causing my knees to buckle for a second. I found her nipple and determined that she was not wearing a bra as I pinched it. She moaned and said, “I see that you want to be a risk taker, but we better save a little for later.”

That was a strange line, but oh well. In my mind I was already peeling her out of her leotard, body stocking, tights or whatever they called them, clamping my mouth on that hard nipple and sucking on it furiously. When we got to the top of the stairs I was fumbling with my keys like a fucking teenager on his first date with a real girl. She just stood there smiling like the Mona Lisa. The ‘come fuck me now’ look on her face was all I needed to see.  The lock finally yielded, and we were in.

She did a cursory look around to see the apartment. The unmade bed, sink full of dishes and stack of pizza boxes on the table. Some well-placed laundry piles were also in view.

“I see you weren’t planning on getting lucky tonight, Sport.”

To try to recover the hot sexual tension between us put my arms out to hug her and said. “No I wasn’t but I hope we can pick up where we left off just outside the door.” 

“Ok we can try, You got a rubber?”

“No. You're not doing anything?”

“Well no, not at the moment. I have a female condom we can use, if we have to.”

“If we have to?”

“Or take me up the ass, if you want to. I don’t mind it at all. I actually cum better that way.”

I was attempting to straighten out the bed covers as best I could while we negotiated the where how and when of our impending fuck.

“I am not a fan of anal at all, just not my style,” I said.

“Ok.” She said as she peeled the body stocking off by herself. A tiny black thong was all that was left on her. Obviously, there was still hope.

I stripped down and saw my cock was at about ¼ stiff. She got into bed, and I did the same. “No entry until I say so. Is that clear?” 

“Yes dear.” I went right for the breasts, and she slowly jerked me back up. 

Vivian opened her leg and repositioned herself next to my face, and at the same time started to give me a sloppy, noisy blow job. Again, not what I had envisioned, nor was her pussy. It was all full of labia folds hanging out like a wad of chewed bubble gum. I knew I had better reciprocate though, at least it tasted ok. Just as I thought I was doing a good job nursing on her clit she said, “Let me get ready, watch if you want to.”

With that she opened her purse and got out a rather large package and opened it. This latex baggie had an additional rubber ring that she folded and shoved deep into her pussy with two fingers. There was a hideous floppy baggie thing hanging out of her cunt. “You must make sure you are in the middle of the condom. It is pre-lubed, but I will guide you. You can go for it now.”

I repositioned and aimed for the center of the baggie, but my cock wanted none of this and it wilted again. Vivian started jerking me again, harder than I like, but got the job accomplished enough for me to put it in. I sank into her as deep as I could, and she locked her feet around my back. I started thrusting slowly, trying to accustom myself to the sensations of fucking a big rubber baggie. Her cunt was not nearly as tight as I expected. Vivian was bucking her hips to keep the rhythm going and I suddenly had to switch to a fantasy to keep it hard. I kept thrusting and thrusting, thrusting and thrusting, thrusting and thrusting. My cock was burning. “Hey partner, you got any lube around here? You're burning me up.” 

“In the nightstand,”  I muttered, so close to nutting in her. I was stuck to the latex as I pulled out and almost dislodged the thing, but she held it in place.

Lube retrieved, and I applied a copious amount into her latex baggie. I reinserted myself and picked up her ankles and put them on my shoulders, leaned forward and folded her up and resumed fucking her. I did focus on watching her little titties bounce as I was going to town, but I could not seem to cross over to an orgasm. Finally, my body gave out and I put her legs down. My cock shrank and slipped out. 

“I am sorry Vivian, so sorry.”

“Don’t be dear, I came a couple of times. Want me to jerk you off?” 

“No babe, he is on fire right now, I am sorry.”

“Don’t be. I got off twice, but my desire left when I saw this apartment, it was just like Jerrimy lived here.” I watched as she pulled the baggie out and laid it on the nightstand with the wrapper. It did nothing but enhance the amount of puffy, fire-red labia hanging down. It absolutely grossed me out.

She dressed and said, “I will let myself out. See you around mate. You do have great stamina.”

That night I did use the female condom to masturbate into. It was a unique feeling of freedom and a very different sensation as I finally emptied my pent-up load. It will take me a while to get over that night of reality. So many things went wrong that night, but a new fantasy of dominating the sexual aspect of an interaction has taken hold.

Vivian has been crossed off of the fantasy list now, but I purchased a dozen female condoms of different types to experiment with.  They are expensive but I do wash and reuse them. The Polyurethane ones and baby powder are my new go-to masturbation sleeves. 

They offer a completely new sensation other than jacking off in a male condom.