A Walk on the Wild Side

I once took a walk on the wild wide and I'm not ashamed to admit I liked it. The idea of a guy sucking my cock never appealed to me, but when I let it happen, I was not sorry, in fact I liked it.

I was living on the upper east side of a big city (guess) and would on occasion walk into one of the local bars that were not reliable checking IDs. This one bar was usually filled with young hot women who lived in the hood. I was bored and without a date for the night, so I walked over to try my luck.

I should say at this point that I am an above average looking guy. I can say this without being accused of being vain because I have a fair amount of success with getting attractive women into bed, which to be honest, is my primary goal in life so my looks are quite useful. Just to be clear about this point, I am not a Brad Pitt but I'm just tall enough (5' 11") and good looking (7 or 8?) enough to bat 300, praise the lord and pass the lubricate. If 300 doesn't seem like a major-league pick-up artist, understand that when I'm in the hunt I always aim for an eight or above (see how I changed metaphors), even if it's last call I am not going home with a three, four or five. I'd rather jerk off to porn. I hate after dropping a load on some dog having to make an exit as quickly as possible to avoid the agony of looking at a plain Jane a minute longer than needed.

Pick up artist pro tip: always dress well. Women will be impressed because they think you have money. I always notice when I wear my $ 1400 suit around town, I get a several more second looks from women than I otherwise would: I can see the thought bubbles over their heads: "that guy is interesting" which translates into a mate value calculation of "he must have money."

When I walked into jailbait bar, I wasn't wearing a suit but a nice jacket and button-down shirt which set me apart from all the young dudes in the place. I was also at least 18 years older than any of them. I walked to the back of the bar where a small dance floor had some couples dancing. I didn't see any interesting prospects, so I headed back to the bar for a drink. When I returned to the dance floor a cute petite blonde caught my eye. I moved in closer to stand next to her. She seemed to be alone.

I leaned in and yelled over the loud music, "Let's dance." Just tell her what to do. Don't ask permission.

I moved onto the dance floor and began to shake my ass around. She hesitated for a moment, gave a hint of a smile and followed me. We danced for a moment or two then the soundtrack changed, and she started to shake her body close to mine, specifically between my legs. I wear boxer shorts to give my best friend plenty of room to grow. With this hot little body moving close it got his attention and he stood up to salute. Her thighs felt his firmness. The hottie was rubbing her thighs and ass against my cock with the purpose of sizing up my package. It evidently met her approval as she pushed her body harder and more often against my crotch. The song hadn't ended when she grabbed my hand and pulled me to bench against a wall. As our asses hit the bench her lips were on mine. We made out as she continued to rub my cock through my pants.

"I'm getting my knob polished tonight," I thought to myself. Then came the catch.

A young guy came over and sat next to her. She broke off the heavy petting and turned to him and said in an excited but insincere manner, "Hey Eric, I didn't know you were here." turning to me, "I'm Jessica, what's your name?"

"Billy," I shook her hand.

The guy leaned over Jessica and offered his hand and said, "Eric." Why the fuck was I shaking his hand?

She placed her head close to Eric's ear and said something which I couldn't hear.

She turned back to me and said, "Let's go to my house and party." She got up and firmly holding my hand pulled me to the exit with Eric leading the way.

I have never had a desire for a threesome with another guy. Two women sure, of course, there is no straight guy on the planet who hasn't had a two-girl fantasy. I've been lucky enough to have had a couple two girl sessions, which I'll tell you about at another time, but sharing a woman with another guy was never on my bucket list. Although, if I'm being honest, I have watched porn with two guys rotisserie fucking a good-looking woman, stroking my cock and shooting a load. The women always seem to be enjoying themselves.

Following Jessica to the exit her thigh high tight-fitting dress gave me a no imagination needed look at her tight body. She had a small but not skinny frame, I hate boney chicks, large tits for her size, maybe a C cup, and a not to small but not too large ass, just enough sub cutaneous fat to send ripples through her ass when you pound her from behind. As we stood on the sidewalk with Eric waving for a cab the streetlights highlighted her shoulder length natural blonde hair. She kind of reminded me of a young Michell Pfeiffer. If she hadn't been at least a nine, I would never have gotten into a cab with her and my new friend Eric. That's my story and I'm sticking with it. She was a good-looking bitch that got whatever she wanted. As it turned out, that night she got what she wanted and so did I.

In the cab Jessica was all over the two of us, kissing us rubbing our cocks through our pants. We pulled up to a building with a doorman she didn't acknowledge, but he gave her a head nod without looking at us. The elevator ride up was more kissing and cock rubbing. She opened the apartment door, turned on the lights and pointed down the hall to what I could see was the kitchen, turning to me, "Be a dear and get us some bottled water out of the fridge would you? My room is down the hall the second on the left."

Good idea to always stay hydrated during a threesome, I guess. That seemed prudent.

She pulled Eric down the hall but I'm guessing he knew where it was. So why was I getting the water? I would have been annoyed except I was taking a survey of the place and frankly I was a bit awed. Her apartment, her parents' home of course, was filled with very expensive furniture and paintings. I walked into a kitchen outfitted with high end appliances and a copper range hood that must have cost 30k. These people were loaded. I grabbed three bottles of designer water out of the Sub-Zero and headed down the hall in the direction of her bedroom.

Of course, on the cab ride over I'd realized I had been set up. This was her MO, pick up some guy, "accidently" run into Eric and bring us back for a two-cock fuck fest. This rich slut always got what she wanted; I was literally the water boy. Fuck it, in for a penny in for a pound. Besides all her cock rubbing through my pants had my balls on a slow burn, I needed my cock inside tight wet young snatch ASAP.

I walked down the hall passing some framed family photos on the walls. I stopped to look at one taken on a beach with a woman and two girls. One of the girls I recognized as Jessica, the woman I assumed was her mother. I could see where she got her looks, her mom was a beauty. A former model/actress marries super rich guy and has two beautiful children. A story as old as time.

When I walked into the bedroom Jessica and Eric were both lying on the bed fully dressed. Which made sense. You need three people for a threesome.

I handed out the drinks, "Your parents are cool with you having two guys in your room?"

After taking a swig of water she said, "They're out of the country for the week."

I sat on the bed with my back against the headboard. I guess they were waiting for me to get things started. I reached for my zipper, pulled it down, reached in and pulled out my cock. I reached for her hand. Her head went toward my lap at once and she wrapped her lips around my cock head. She was an eager and experienced cocksucker. She made sure my cock was well lubricated with spit, she opened her mouth wide and covered her teeth with lips and creating good suction.

Eric was very patient while Jessica sucked my dick, drinking his water not even looking our way. Then she moved her head over to Eric's lap unzipping his pants and taking out his cock. Her sweet ass now facing me, with both hands I pushed up her dress over her hips up to her waist. I slipped the fingers of both hands under the elastic of her lacy panties and pulled them down her ass. She helpfully lifted her body a bit off the bed to facilitate the panty removal operation. I forcefully spread her legs as wide as I could. Her pussy was shaved, and the labia lips already glistened with moisture. Even her pussy was gorgeous, her outer lips, labia major, completely concealed her labia minora. On most women the inner lips protrude past the outer lips. I slid my right-hand forefinger and middle finger up and down over the outer folds of skin.

Pro-Tip: If you want to be an expert pussy eater and you should want to be one, watch lesbian porn. Real lesbians, women who genuinely only want to fuck other women, not the performers who do lesbian scenes because it's expected. Watch the ones who love to go down on a woman and can really make another woman orgasm. I know woman can fake it but if you watch enough porn you can learn to spot a real body spasm, skin flushing around the neck and chest orgasm. Pay attention to everything they do with their fingers, hands and of course mouth. In addition, watch masturbation scenes. Pay attention to how women touch their themselves to bring themselves off. It's not the way a guy naturally thinks a woman would want to be masturbated or have her pussy eaten. Make that your homework assignment to watch porn with women alone or two women together. Think of porn as homework, eating pussy the field work.

I continued to explore her pussy with my fingers taking my time, giving her clit some attention as I picked up her wetness with my fingertips. Then I lowered my head and gently licked her labia minora. Using my two fingers to spread her open, I traced a big circle around her opening with my tongue, first counterclockwise then clockwise. Hearing her mouth stuffed with cock moans I slowly slipped my forefinger and middle finger into her vagina, at first just a bit, then pulled out, then pushed in a bit more until both fingers were in her up to the third joint. I searched for the little pad of flesh inside behind the clitoris using my forefinger fingertip to firmly rub the spot. I did this slowly, it's important to start out slow. There is plenty of time later for fast and hard cock pounding. It really pays off to slowly bring up a woman to boil even if you've been at a boil for the last two hours. It's not about being a generous lover or any kind of altruistic bullshit, it's purely selfish. When a woman is totally lost in orgiastic bliss, she'll do any kind of depraved sex you want. Afterwards, when you leave, she is going think about you when she plays with herself hankering for a cock fix from you. In other words, if you want it, you'll get plenty of repeat business.

I kept at my task till I got her moaning loudly with occasionally Eric's cock dropping out of her mouth. At some point I thought I heard a door open. In an apartment I assume it's a door opening or closing on another floor. I was getting overheated. I got off the bed and stripped naked, throwing my clothes on a chair and was back on the bed. I pushed both her legs back towards her chest and positioned myself between her legs. I took my dick in hand and rubbed the head back and forth to pick some lubrication from her cunt.

With my manhandling of her body Eric's cock fell out her mouth. He took the opportunity to leisurely get undressed. I pulled down the top of Jessica's dress to her waist to reveal her big firm tits with surprisingly large areolas and flat nipples.

With enough lubrication on the head of my penis I slowly pushed forward entering her very tight hole, pulling out and then pushing more of the cock back into her well lubricated hole.

Pro-tip: make sure the pussy or your dick is wet. Use spit or whatever lubricate is handy. Never enter dry.

Soon the entire length of my cock was smoothly working in and out of her hole. By this time Eric was naked and straddled Jessica's face, lowering his balls into her mouth. She lovingly sucked his balls. He moved forward, towards me. He now looked directly at my cock slipping in and out of Jessica's cunt. He took his right hand placing his fingertips on her clit, rubbing it back and forth. His fingers were almost touching my cock. I had never had a man's hand so close to my cock, but before I could object, he slid all his fingers around her cunt and my cock. He moved his body closer to the intersection of me and Jessica continuing to exert pressure on her pussy lips and my cock.

I should admit at this point that I always suspected this was where this threesome was headed. She wants two cocks to fuck her, and he wants a straight guy's dick to suck.

He moved closer still, his face now almost laying on Jessica's lower belly. I pulled my cock out for a moment and he at once put his fingers around my and cock and stuffed the head into his mouth. He worked very quickly and hard, as if to prove to a straight guy, that getting your cock sucked by a guy is worth it. To tell you the truth it was. The guy sucked dick like a champ. At least fifty percent of women that I've ever been with haven't sucked my dick as well as Eric. Which makes sense, a guy knows what a guy likes. I could shove almost all my cock down his throat, and he created lots of suction on the up stroke.

He worked my dick for a while then I took it out his mouth and shoved it back into Jessica's hole. She groaned loudly. This went on for quite a while, alternating my dick between Eric's mouth and Jessica's sweet hole. I have a good deal of self-control holding off ejaculating but alternating between a mouth and cunt was pushing my endurance. It felt so good I wanted to hold off ejaculating as long as I could.

Pro-tip: Do lots of sit ups, exercise your core, abs for a better hard on and delayed orgasms.

I abruptly got off the bed and went to the nightstand to get a drink of water. Out of the corner of my eye I thought I saw movement by the door to bedroom. It was open. Did I leave it open? I walked over to the door and out into the hallway.

Jessica said, "What's wrong, where are going?"

The door to the room next to Jessica's was open and light was on in the room.

I went back into Jessica's room, "I think some else is here."

Jessica said, "It's my sister don't worry about her she wouldn't bother us. Come back over here we want to both suck your cock." She said it like she was ordering a coke.

I walked over to stand at the side of the bed. She was naked at this point. They both kneeled side by side on the bed positioning their faces at cock level. He grabbed my dick first, sucked a bit then passed it to her to hungrily swallow. This wasn't bad at all; two expert cocksuckers were polishing my knob. Who cared if one of them was a guy? A good cocksucker is a good cocksucker and I had to admit he was good. I suspected she learned a thing or two from Eric on the finer points of dick sucking.

Then I had not very original idea, "Let's do a DP. Every have two dicks in you at once?"

I figure if I am going to be in a threesome with a guy, a DP is almost an obligation to the lady. This might be my only chance to check it off my bucket list. I don't need to worry about "crossing swords" with the guy; my cock has already been in his mouth.

Jessica looked up at me with my cock still in her hand, "A cock in my ass and one in my pussy?"

"Yeah, that's how its normally done. Come on I'm not the first guy you two have brought back for a threesome?" They both betrayed themselves with grins.

I opened her nightstand drawer which of course was filled with sex toys and lubricate.

"You get on top of him, I'm filling your ass. Get on your back and you mount him."

Without saying a word, they both just did what they were told. They both wanted to be told what to do by an older man. He went on his back, and she straddled him and lowered herself down onto his shaft in one stroke.

At this point I should describe Eric just a little. He was shorter than me, maybe 5'7' brown hair, good looking but not a pretty boy. Maybe Justin Timberlake's younger brother? Someone with good gaydar could tell he was gay. If I had been paying him any attention to him, I might have. And yes, he had a decent sized cock, perhaps even bigger than mine. How is that possible? A shorter guy has a bigger cock than a taller guy. Life isn't fair. But what am a complaining about, I am about to stick my ass into a hot blonde's tight ass hole. It should be interesting with another cock right next door, and interesting it was.

I lubed up my cock, positioned myself behind her between his legs which Eric had courteously spread wide. My cock slipped in easily after the first barrier. Eric got into a slow steady rhythm which I copied. Jessica let out low guttural sound with each thrust of our cocks.

She now alternated between open mouthed "Ah" and "Ohs" with the periodic, "OH fuck yeah... Fuck me," and the like.

I was familiar with the sensation of ass fucking a woman with dildo her pussy, I did it often with an ex, but that's another story. This was similar yet different. Her tight asshole and the stiffness of his cock in her pussy only separated by whatever the membrane is called that separates a woman's vagina from her colon (?) was a unique sensation.

By this point my balls were boiling. I couldn't hold out any longer even if I had wanted and I didn't.

"I'm going to cum in your ass, OK?"

A plaintive, "Yes" passed her lips.

I pulled out anyway and shot three large loads on her ass hole which quickly dribbled down onto Eric's balls. I fell on my back on the bed.

He sped up his thrusting into her and quickly ejaculated deep in her cunt.

After a while, I got up from the bed and said, "I'm getting more water."

Naked, I walked into the hallway and headed for the kitchen. They lights were on in the kitchen. Did I leave them on?

When I stepped into the kitchen, I pulled up short. At the counter on a bar stool was a woman in a bathrobe. I stood there, as she looked me up and down, lingering on my still glazed with sperm and pussy juice cock.

"Sorry, I'm just getting some drinks. I didn't know anyone was home."

I didn't try to cover myself. I could tell she really didn't mind taking in my naked form. I went over to the sink to wash my hands. I wouldn't have if I was alone, but it felt more, I don't know, courteous to wash my sex covered hands before opening appliances.

"Don't worry about it. We're used to having my sister's boy toys come and go. Your kind of old to be a boy toy?"

It never occurred to me that Jessica wasn't the legal age of consent in the state of XX.

She could read the look on my face, "Don't worry my sister is legal. She's kind of young for you, isn't she?"

"I don't mind if she doesn't."

"Of course, you don't, she's a hottie. A whore but a hottie."

I opened the fridge and looked for more water, found some beer, "Yes she is good looking."

I pulled out three bottles of beer and used my naked butt to close the refrigerator door, "Your pretty good looking yourself. You both have your mother's looks."

I could see the wheels turn: does this guy know my family?

I explained, "I looked at the photos in the hallway. I bet she was a model and actress."

As she got up from the bar stool she said, "Yeah she was," then moved towards the hallway.

I said, "Nice to meet you," as she left the kitchen heading, I assumed, to her bedroom.

I paused before I headed back to Jessica's bedroom.

When I got back both were lying in bed with Jessica on her stomach with Eric's cock in her mouth.