“Do you want to cum in my mouth?”   As soon as she said that, my heart skipped a beat and my fucking lost a few strokes.  It was so mater of fact, like “Do you want cream in your coffee, Sir?”  It was the first time a woman had asked me that question, and I had had lots of partners in many sexual settings over the years before.

Chicago… 30 Years Ago… A  Memoir

It was winter, and typical Chicago weather… cold and snowy.  I was in charge of the bar at a nice restaurant in the shadow of the Sears Tower, just west of the Loop.  We were one of the sponsors for the yearly production of A Christmas Carol at the famed Goodman Theater, and offered a package Olde Fashioned English Feast in the Dickens tradition with transportation to the theater and back for ticket holders.  The final performance was on New Years Eve and the restaurant was hosting a party for the staff and backstage crew of the theater after the show.

The turnout was pretty good… who doesn’t like free food and drink.  One of the guests was alone and hung out at the bar talking to friends, and as the partygoers left for other parties or home, she was talking to me.  Not flirting, just talking as she seemed lonely, and I was enjoying the attention of a pretty girl half my age.  I found out she was a lighting technician and was now out of a job, so the closing was bittersweet, as she was not needed for the next show.  Beth was an attractive woman in her early twenties with a full figure, but seemed ill at ease in her dress, like she was not used to dressing up, and certainly wearing heels.   As the party wound down and I gave last call, she asked me if I would dance with her… that was how she put it…. and I told her I would love that.  By that time of night, the music was slow and dreamy and she put her arms around my neck and melted against me.  I was just there to dance, but could not stop the stirring in my pants and I knew she could feel me stiffening against her.  We didn’t talk or get romantic, but it felt good to hold and feel each other. We danced the last dance and went back to the bar. I started to clean up the bar and she hung around watching.  I was deciding what my move should be, when she asked me if I wanted a ride, since it was “snowing and you have to take the train home”, she said.  She had made the move, and I appreciated the ride.

Her car was an old yellow Datsun, named Woodstock.  I don’t know why women like to name their cars, but my second wife’s baby-blue VW Beatle was named Wolfgang.  I hate driving in the snow, but she was good at it and we got to my place safely.  Of course I asked her in and soon we were on the couch kissing and getting naked.  I always liked to leave a woman’s bra and panties on and suck and kiss through the material before removing, which I thought was sexy and hadn’t had complaints so I guess they thought so too.  Beth had small conical shaped breasts with long nipples which I sucked and nibbled as she stroked my cock, letting go as I slid down her body to kiss around the top of her mound and stroke her inner thighs, circling closer to her panties.  Soon kissing and sucking, drawing the silken fabric into my mouth.  I am tempted to say I ripped them off with my teeth, but I didn’t and gently slid them down her legs with one hand as I palmed her mound with my other, thumbing the hairy slit.  She was pretty silent and I hoped she was enjoying the sex, as I kissed and parted her lips with my tongue, sucking her clit into my mouth.  I felt her hand on the back of my head as she began to thrust her hips up toward me.  Her eyes were closed and I could see her fingers squeezing one of her nipples.  I wanted to try to give her an orgasm but I also wanted to fuck her and my cock was winning out, as I moved up and rubbed the head of my dick up and around the entrance to her well lubed slit.  God, I was moaning and she was still silent, breathing between her teeth as I pushed inside her.  After a few strokes, like an idiot, I asked her if she liked it and she dug her nails in my back.  Beth’s full ass felt good in my hands as I squeezed and drove my cock slowly in and out of her pussy.  I rose up so my shaft was rubbing against her clit before pushing back up inside.   I asked her if she liked to be fucked from behind, she said yes but not to stop what I was doing.  Thinking I was going to make her cum was having an effect on me and I imagine she could sense it, because out of the blue she said, “Do you want to cum in my mouth”.  Now, that blew me away, quite literally as I plunged deeper and faster saying “Yes!”.  Soon, I rose up and she grabbed my cock pulling me toward her.  I made it as far as her chest covering her neck with my jizz.  She drew the head into her mouth and sucked me softly.  Beth stayed the night for sleep and more sex.

We got together a few more times to have dinner or go drinking and have sex, until one night she came into my neighborhood bar and introduced me to her boyfriend.  Now that was a surprise.  She said she might be going back to college, we lost touch and I never saw her again. But, I will never forget her and the night she asked me if I wanted to cum in her mouth.

My first experiment with Risky Sex was when I was 14 or 15…  

We were on a train to San Francisco with a church group.  My pal and I met some girls from another town, and we had this little pint of whiskey we had swiped from a grocery store and we thought we were pretty hot stuff.  The girls were our age, or maybe a little older, and they started talking about sex, of which we didn’t know too much.  Well, the one I was sitting next to put her jacket over our laps, slid her hand into my pants and started rubbing my cock.  I did the same till I felt her wiry pubic hair and tried to finger her pussy, but the angle was wrong so I could only rub the lips.  I didn’t know what the hell I was doing; but it was exciting, I was hard, and I came quickly.  She laughed and rubbed the jizz from her hand on my jeans, and that was the end of that.

While we were doing that, trying to be so stealth, one of the female chaperones walked by and stared at us.  I was kind of scared the whole time we would be caught, and about died when she looked straight at me, but nothing was ever said.

That was the first time someone touched my cock other than I, and it would be some years before someone, other than I, made me ejaculate.

You are lying on the kitchen table I’m sitting on top of you my left hand pushed against your chest at the base of your neck holding you down as I squeeze your nipples as hard as I can pulling and twisting them you have tears in your eyes but I think you like it you’re telling me to stop but there is no one nearby to hear you my pants are unbuttoned and my penis is out hard and stiff I need to stroke my cock and I tell you that I’m going to remove my hand from your neck and if you move I will slap you and if you scream I will push a towel into your mouth I ask if you agree and you nod your head eyes wide open breathing hard I can feel your hips moving beneath me and you have stopped straining and struggling as much I’ve begun to pump my cock now and reach around and push my fingers against your wet panties pushing them into your cunt you are moaning now whimpering and I can feel the jizz building and I begin to squeeze and pull on my ballsack hard as I can furiously stroking my cock as I stare into your eyes I can’t hold back any longer I arch forward and spill my semen onto your neck your mouth is open and I know you want my cock in your mouth to suck the last drops but I relax back and begin to swirl the head of my cock against your nipples coating them with my jism before leaning down to suck them into my mouth I tell you I want to fuck you and you shake your head no pleading with me to let you go and you are struggling again Gwen stop it I shout and ask you if you know what happens to bad girls and you shake your head fear in your eyes I’m off you now and flip you over on the table your legs are hanging down your ass is turned up I’m pushing against your back holding you down and begin to spank you not too hard at first and your yelling is beginning to turn me on I see that my cock is beginning to get hard again I slap you harder now In between each slap I squeeze your ass cheek or push my fingers against your cunt lips you’re crying but I know you like it I think I’m stiff enough to fuck you I tell you that and you begin to struggle again saying no when I slap your ass three times as hard as I can you stop moving sliding your panties down off your ass and pushing my fingers inside you I get them wet with your juices so I can lube my cock before pushing it against your opening you plead no and I tell you if you don’t relax and accept that you’re going to get fucked I’ll fuck you in the ass instead I guess that was a good threat because you stop fighting and I begin pushing the head of my cock between your cunt lips just sliding it in and out just the tip teasing you as you begin to moan and start begging me to fuck you to push my cock inside you and fuck you hard the kitchen table is beginning to slide along the floor as we fuck furiously you pushing up to meet my thrusts and you tell me not to shoot inside you that you want to see me cum but I’ve decided to come on your ass and as I pull out I begin to spurt and pushing my penis against your anus I cover your pink hole with my cum lick it up and push your tongue inside me you say as I try to catch my breath.

Afterwards, I get dressed, you pay me, I leave.

Today I was on a country road and passed a horse farm.  A friend’s kids had taken horseback ridding lessons there a few years ago, and I had picked them up for her a few times.  They were learning English style and that was fun to watch as it involved discipline and jumping over barriers.   The woman who owns the horse farm is an attractive tall brunette with a lanky form and a sweet disposition.  She was a champion rider and her horse barn boasts many ribbons and trophies. Other kids I knew learned Western style riding, at other horse farms, which was more racing and games with barrels and such. They would all participate at the county fair each year and it is fun to watch and take photos of the kids in action.

It was always a treat when the teacher would ride at the fair, to see her and her horse perform, going through the paces and hitting the jumps.  At the ranch, she dressed in jeans and loose western shirts, but at the fair she would be in the English riding uniform of black jacket, starched white shirt and tan breeches with tall black boots.  She was impressive and incredibly sexy.  She is also very married.

I always look for her when I pass the farm and sometimes see her in one of the fields with her horses.  I would love to fuck her.  I thought of that as I drove by today, fucking her.  I suddenly wondered if being an experienced horse rider, no matter English or Western, would make a woman better at fucking.  Better at Cowgirl Style?  For her to climb on top and ease my cock inside her and begin to buck.  Would all that saddle time give her movements other women might not know or think to do.  I’ve always enjoyed a woman lying on top of me, her weight pressing down, just holding her in my arms or squeezing her ass in my hands, slowly grinding into each other.  Then she, sliding up and beginning to move back and forth, up and down, squeezing my penis inside her vagina.  I had one lover who could do that and then switch around the other way without losing my cock from her moist embrace.

Fucking Cowgirl Style requires technique and imagination, is not for everyone and I’ve found not all women are good at it or enjoy being on top.  Some said they didn’t like doing it, as it made them feel they were being slutty.  They usually liked the lights out too.  They were fun to have sex with and try to shock. I loved to try to get them to talk dirty.  To maybe teach to be on top and enjoy the feeling.

I enjoy being on the bottom, as the view is scrumptious and I love to squeeze her breasts and pull her down to take a nipple in my mouth and suck as she is sliding up and down on my cock.  Reverse Cowgirl is fun, and better if she likes anal play and I can slide my thumb in her ass.  Even more exciting when she does the same to me, as she is at the right angle.  One friend would squeeze my balls like a pommel as she bucked up and down.

Unfortunately, I don’t know any women who ride horses that aren’t married.  And I don’t know their husbands well enough to ask how their Cowgirl is in bed. Maybe someone reading this who has been fucked by a real Cowgirl can tell me.  Or, a Cowgirl out there will share her secrets.

“Come in and close the door, please.”

He had never been called to her office before, in fact, he had never even been on the sixth floor. It has to be the promotion he has been waiting for.

“Mr. Young, it’s come to my attention that you have been abusing company equipment. One of the girls came in on Saturday to pick up her check and saw you in the media room. Do you remember what you were doing in the media room on Saturday?”

He began to feel faint, of course he remembered what he was doing. God, what to say, maybe she doesn’t know? God wasn’t helping so he said nothing.

“It is my understanding you were watching pornography and masturbating. She said she watched you for some time.”

Now, he really felt faint. That’s why May and Lucy were laughing and wouldn’t look him in the eye when he brought them their coffee this morning. Those bitches, now the whole company will know. He began to protest…

“Stop! Do you realize it is against company policy to use company property for personal use, and on company time?”

He could think of nothing to get out of this one. How do I look contrite, he wondered, biting his bottom lip. “I’m sorry, I won’t do it again.”

“You are damn right you won’t do it again, but I am a fair person and believe in second chances. When I asked her why she watched for so long, she said you had a very nice penis and she enjoyed watching. I would like to judge for myself. Would you like to show me your penis, Mr. Young?”

“Uh, I don’t think that would be appropriate.”

“I don’t think what you did was appropriate, jerking off when you were supposed to be working, and in front of a young woman?”

“I didn’t know she was watching.”

“That doesn’t matter. Do you like your job, Mr. Young? If you do, I would suggest you unzip now and show me your cock.”

Strangely, he felt an erection starting, and he did want to keep his job. So he unzipped as asked and dropped his pants to his ankles. She was staring at his crotch, and as he pulled his boxers down his cock sprang out. Awkwardly he stood there waiting, hoping she liked what she saw, his penis beginning to swell and stiffen more.

“Show me what you do next, I supposed you have a routine?”

He nodded and began to stroke his penis, the bulbous head popping out of his hand as he masturbated, up and down.

“Does that feel good?”

“Yes, but it’s kind of embarrassing.” He is fully erect now and finds he is turned on masturbating for his boss.

“I don’t care, I want a good show. Do you think you can make yourself have an orgasm? I’d really like to see that, no, I want to see that. Bring that chair over here so I can watch.”

He did as he was told, feeling silly, his pants still around his ankles. But once he settled in, closed his eyes and began to pump his cock, the embarassment began to fade a bit. He would give her a show she wouldn’t forget, he decided. Starting slow at first, so she could get a good look at his cock, he began to squeeze his balls as he massaged the head of his penis, hoping it wouldn’t take too long, and he could escape.

“I want to see you come, but don’t get any on the carpet, come in your hand, I want to see you come in your hand!”

He spit on his hand, making it slick, that always helped, and he felt the jizz beginning to form. “Oh, God, oh, oh, OoohGod!!!”, he began to moan, half for real and half for dramatic effect. Peeking thru his eyelashes he saw that she had wheeled her chair from behind the desk and was leaning forward watching intently. He had to admit it was exciting having an audience, and he could swear he saw her lick her lips. He fantasized undressing her, even though she had to be forty, as he held the base of his penis in his left hand and stroked the shaft with the other, harder and faster now, his ass clenching and beginning to squirm in the chair. He was breathing hard and moaning louder, this time all for real, as he dutifully shot his load into his hand, collapsing back into the chair, spent, his cock going limp, lolling against his leg, his hand holding out a palm full of pearlescence jizzum for her inspection. She handed him a box of tissue.

“Pull your pants up and get back to work, Mr. Young. Tomorrow when you come to in, report to Personnel, I have a new position for you.”

I woke up thinking of your photo and raise the window shade to bring in the morning light as I pull back the bed covers to expose my stiffening penis I need to see your photo again and fumbling in my haste reach for my phone stabbing the screen till our messages come up to the sight of your full breasts pushing against a lacy red bra and it’s causing the blood to boil and surge into my cock as I watch it grow fat and hard I think how you are so naughty you knew what you were doing when you sent me this photo that you would create lust be willing me to touch myself and I’m giving in to you now as I begin to squeeze my balls slowly and gently watching my cock rise and fall as I tug on the sac I’m pulling harder now as the waves of pleasure become more intense and my hips begin to rise and fall with the motion as my balls are pushing against each other rolling in my hand God it feels so good as I stare at your cleavage and your oh-so-smug red lips imagining all manner of things in my mind as I begin to stroke my penis with my fingers sliding up and down the shaft slowly at first squeezing and massaging the swollen cockhead then faster and faster and fuck I want to cum I’m pulling on my scrotum harder now pre-cum sticky on my fingers as I pump my cock in my fist I hadn’t bothered with lube and my dick is getting sore as I’m squeezing harder stroking faster my hand a blur pumping and twisting my cock my legs taut ass bouncing the pain only adding to the pleasure Ooooh Fuck I’m going to cum now spurting jism floods my hand the smell in the air invading my nostrils as my cock is receding shrinking and I massage my scrotum with warm semen.  

I’m spent, panting for breath, totally at peace and loving your red brassiere. 

Romance and Erotica

NSFW