Friends with Benefits

An opportunity for promotion caused me to put in a bid on a position in Chicago. Success! Now I must disentangle myself from several real nice girls here in Rochester.

My first week at the new job was hectic as would be expected. Meeting new people, figuring out my boss and what made him tick, and so forth. One thing I hadn't worked on yet was new girlfriends. In Rochester I had a firm policy of not dating anyone within the company. The division there was smaller than Chicago. I was counseled by a very wise person, my dad, not to dip my wick where I worked. Too much gossip, intrigue, possible bad feelings. I planned on a similar policy in Chicago.

My first weekend was spent getting my new apartment organized. The next week I did a bit of after-work socializing with some teammates (all guys). They filled me on places to eat and not eat, the hot social scenes, that sort of thing. The place to be Fridays after work was Simone's. It was the meeting and hook-up spot. I was promised lots of eye candy. And being the new guy I would be an attraction. I begged off since I had to go back to Rochester over the weekend to wrap up some things (girls).

The Friday after that I joined with three of my new buds. They introduced me around. The crowd was young, 20's, early 30's, and very good looking. I guess not too surprising since we are a media company.

Several girls looked real good and tried to catch my eye. Remembering my dad's advice I reluctantly didn't pursue several leads. My new teammates gave me some introductions outside the company. Within a couple of weeks I was working on one gal.

My interest at age 23 was sex without emotional complications. I sought out girls who were of a similar mind or claimed to be. An "older" woman taught me years ago how to be a good lover. I learned if I gave girls good conversation and great climaxes I would have lots of pussy. I wasn't looking for long term relationship. I didn't judge. If the girls looked good, had great bodies, and knew how to fuck -- I was their man.

Lest I seem too egotistical (well maybe a little), let me describe myself: 6-3, 190 lbs. Runner's body (I run three miles a day). Handsome face. Good personality. Oh, and a big cock -- my prize possession.

Helen became my first Chicago girl. She was step-sister to Bill, one of the guys at work. He said she was sexy and wild. Bill told her to come to Friday's gathering, said it would be worth her while. We grabbed a table away from the crowd and chatted. Helen was 21, looked 16, lost her virginity at 15, kept several guys on her string. Loved sex, played some with girls. Straight out I told her I didn't mind other guys fucking her but that I was going to be her go-to guy for sex. Pretty direct considering we only met half-an-hour earlier.

Actually she was a nice girl and we talked until the crowd thinned out. We had a date for the next night.

We met for some Chicago style pizza - deep-dish vs the thin "slice" I ate back home. Cathy was witty and fun to talk to. A slender blond, not much on top but a sexy bubble butt. Very pretty face. We shared stories and backgrounds. She wasn't near as wild as Bill claimed but definitely liked sex. She also liked me and I liked her. I was honest. Not interested in settling down, looking for a friend with benefits. We headed back to my place.

"Nice place, John."

"Thanks. Still organizing my stuff. I would have liked a little bigger place. Chicago rents are higher than Rochester."

"Fuck me," as she started undressing.

I had hoped for a good time together. I hadn't had sex since moving and was horny.

My "tutor" back when taught me how to eat pussy like a champ. She said "do it right and you'll have all the pussy you want." I found that to be true.

Cathy was modest in the boob department but her nipples were long. After some butterfly kisses and kisses behind her ear I moved down. Sucking like a hungry baby I worked on first one and then the other nipple.

A bit later I worked further down, kissing her on her sides just above her hips. Then stuck my tongue in her bellybutton. Especially if it's a "inney'," my tutor said, "use it like a little pussy." My hands softly rubbed up and down her legs.

I moved further down. "You have a beautiful pussy, Cathy. I love bare!" as I used the tip of my tongue to gently spread her lips.

I worked my way between her lips using my tongue as a cock. She moved her hips up and down, matching my thrusts. She reached down and spread her lips and I went deeper. Then I switched to licking up and down her slit, hitting her clit each time.

Using both hands she pulled my head towards her, mashing my face in her pussy. She murmured "Oh ... Oh" and came with a shudder.

"Wow, John. You are so good. I rarely climaxe from just pussy eating. I want your cock. Do me doggy style."

I took my cock in hand and rubbed the head up and down her slit. The head slipped into her hole half way. Then I pulled back out. I continued to tease her with just the head. Then in one thrust I was half way in. Cathy grunted. I pulled out except for half of my cock head. Then another thrust, this time three-fourths in. Back out and then a final thrust. I held steady, fully embedded.

"God, how big are you? I think you went into my cervix. Stay still for a moment and let me get used to that monster cock of yours.

I started with long strokes, then short ones staying half-way. Then some long strokes again. I put my left hand under her from the front to guide my cock. That way I could pull out completely and shove back in. She was getting close. Using my index and second finger I massaged her clit in time with my strokes. Her pussy gushed as she climaxed. I bottomed out with my cock as I drove my cum deep into her body.

I rolled off and to her side, spooning. Neither of us spoke for several minutes, just enjoying the relaxed come-down from really good sex. With my limp cock nestled in the crack of her ass, I reached up and caressed her nipples.

"Mm, feels good. That was very nice!"

"Thank you, Cathy. We were rather good together, don't you think?"

"The best! You seemed to know how to push all of my buttons."

"I had an older lover some years ago who took my virginity. She gave me lessons in satisfying a woman."

"It shows. I need to tell you, I currently see two guys, not at the same time of course. I like them a lot. And I like lots of sex. You said you weren't looking for a serious relationship. More like friends with benefits, you said. How about we be friends and I'll give you the benefits?"

We made a date for the following Saturday afternoon. Chicago had some real possibilities.

"Well, how did it go with Cathy," Bill asked me on Monday. "You guys seem to hit it off."

"She's a very nice girl. We have a date next weekend," I answered without mentioning last Friday. Not his business.

This week I was placed into several media projects to get me started. New people, new places, new things to learn. The week went fast.

I picked Cathy up and we headed to a local grill and bar she liked. A little drinking and some good food and we headed back to my place.

I ate her pussy. She gave me a blowjob. "You need to stop now. I want to come in your pussy," which I did. Much too fast, however, for her to get going. OK, now for some magic from my tutor.

I slid down her tummy and spread her legs. "You have a beautiful pussy. So delicate. I need to kiss it and make it feel good." I used my tongue to spread her lips.

"What are you doing, John? Your cum is inside me."

"Lay back and enjoy, Cathy. I'm going to make you feel really good."

"But I'm leaking your stuff."

I didn't respond since my mouth was now on her pussy. I spread her lips and slid my tongue up and down, in and out. "Use your pussy muscles, push my cum out so I can clean you up." Several globs of creamy liquid appeared which I promptly lapped up. A few moments later Cathy came, giving me an additional burst of cream.

She lay there with her legs splayed out, her red, puffy pussy on display. A satisfied smile on her face. I was happy I could give her such a good release.

"When you came in me so quickly I thought to myself, "Oh, man, I was getting close. Damn! And then you ate my creampie. You are full of all sorts of surprises."

"Thanks. I'm not usually so quick on the trigger but your blowjob was exquisite. Your fault!"

"How about me playing with it and see if we can get it going again," she said with a smirk and stroked my limp weeny. "We have plenty of time.

"This is a really big cock, John. Even flaccid it's as big as some of my past boyfriends when they were hard. Look, I can get both my hands on and the head is still sticking out."

A few minutes later my cock was deep into Cathy's pussy. She had several small climaxes followed by one huge one as I finally filled her. We snugged a while.

"What time is it? Oh sorry, John, I need to get going. One of my other guys is coming to pick me up. I'm going to keep your cum in my pussy and see if he notices!"

I was surprised but not offended. I did say no serious relationship, just friends with benefits. Cathy knows how to keep a guy in his place. I prefer honesty versus games.

"So how was he?" Gwen asked the next morning. "Lots of fun," was Cathy's cryptic answer to her roommate's question. "Come on Cathy, tell us more," Mindy, her other roommate, prodded.

"We went to Antonio's, then back to his place."

"And ...?" Mindy persisted.

"We had sex. Lots of it. He ate my pussy and I came. A first for me that way. I sucked his cock as a warmup. He fucked me but came pretty fast. I thought to myself 'damn, that was too quick'. But he didn't leave me hanging. Quite the contrary. He ate my pussy again, cum and all. And then gave me a first-class fuck. Then I left. I had a date with one of my boyfriends."

"Wait a minute! He ate his cum out of your pussy?"

"Yep, most erotic thing I ever experienced."

"Cathy, you got fucked by a gay guy. Don't you realize he was just using you as an excuse to eat his own cum. Gross!"

"It wasn't like that at all, Mindy. He said some years ago an older woman taught him about sex, including eating pussy after fucking. Let me tell you, I came three times with him. An all-time record for me in one session. That's not gay.

"By the way, Mindy, he has a thick ten-inch cock. The biggest I ever had. And when I left his cum was still in my pussy for Bobby."

"You are so bad! Did Bobby know?"

"When he picked me up my pussy was still full of John's stuff. We went to dinner. My pussy felt squishy and I kept squirming in my chair. I finally told Bobby I was so horny for him that I was leaking. We went back to his place. He really loved my well-lubricated pussy! He had a good time and I certainly did!

"What's next with this sexual wonder? When can we meet him?" Gwen finally spoke up.

"I'll set up something for next weekend."

"I hope you don't get mad at me, John. But my roommates wanted a complete recap of our date on Saturday. We share all our sexual adventures so I gave them the details. They think you're gay."

"What?!"

"Well, I told them how you ate my pussy after fucking me. Mindy said no straight guy would ever do that. So you must be gay, she said."

"So how am I going to prove otherwise? We were good in bed together. Doesn't that count for something?"

"John, you don't have anything to prove to me. No guy has ever satisfied me like you did. What are you doing this Saturday? Let's spend the day in bed.

"I just had an idea... you come over one night this week. I'll let them both stroke your big cock. If that doesn't do it I don't know what would."

"And if that doesn't convince them will you want me to fuck them? Or fuck you in front of them? This is a stupid conversation."

Cathy giggled. "Now that might be fun...."

"Forget about them. I'll pick you up at 2 on Saturday. We'll figure out something to do, won't we? And you can return with a big smile and a full pussy. To hell with them."

Young women can be so stupid.

The new job kept me busy all week. Come Saturday Cathy introduced me to her roommates. I'm not sure what they expected. Perhaps some skinny dork with pimples, tattoo of "mother," and limp wrists.

"I had to laugh," Cathy said as we drove away. "Did you see Gwen's expression when I rubbed your crotch and said let's go and have some fun?"

We had a fine time in bed - a repeat of last week except I didn't shoot my wad too soon. So Cathy had four climaxes, one better than our first time. Something she can brag about to her stupid roommates. I liked Cathy.

A week later we were propped up in bed sipping our third margaritas. I was snuggled up to her, she was fondling my limp cock.

"You really have the greatest cock," she said as she examined her discovery. "It's not only my biggest but it shoots so much cum. Think you can get it going again?"

"If you kiss it and make well, maybe ..."

"Do you like my body? I'm not even a B cup on top."

"Fine with me, they're nice and perky. Long nipples," I figured she was fishing for a complement. "I like slender girls. You have slender hips and a bubble butt. A teenager's body. That I like. You probably look delicious in a bikini."

"Some guys say I look sixteen..."

"Yeah, maybe so. And I'm the older guy taking advantage of a sweet young thing. Let's go to a pool sometime so I can show you off."

"I do have a really tiny bikini. I haven't worn it yet, too embarrassed. I will if you want me to.

"Oh, I don't think I told you: after our second time I saved your cum in my pussy. Two hours later Bobby, one of my other boyfriends, was fucking me. He loved how juicy I was! Should I tell him it was your cum?" she giggled.

"I would think not."

"Maybe I should bring you his creampie?"

I knew she was teasing. Probably.

"Do you fuck girls in the ass with this cock?"

"Only a couple of times. Hardly any will let me."

"I'm not surprised. Bobby likes to do it to me. Of course his cock is two-thirds yours. You would tear me up. Hey, how about the three of us get together. He can fuck me in the ass and you can fuck my pussy. I've always wanted to do a DP."

"You're irrepressible, Cathy", I said with a laugh. "Stop talking and suck my cock."

She was fun. I enjoyed the repartee. And she did look sixteen. Now I had one fuck buddy, at least one more to go. But most of my social contacts were at the Friday company gatherings. I was too new to Chicago. It seemed a bit crass to ask Cathy to set me up with other girls!

**********

"What are you doing Saturday?," Steven, a fellow in the next office asked. "Several of us are going to the races. Want to come?"

"Races?"

"Arlington Park. Horse races."

"Oh, I don't think so. I don't know anything about horses and don't think I want to."

"We don't either. But we have six tickets to the club house. I'm taking Lois. Lynn is taking Alice, you don't know her. Come on, we'll have fun."

"OK. What about the sixth ticket? I won't have a date," I wasn't interested in bringing Cathy into this group.

"Don't worry. I'll ask Lois to see if she can come up with someone. Several of her friends are real lookers."

He was right. Sheryl was pleasant company. And definitely a "looker." The horseracing was actually fun to watch. I placed a few small bets, lost them all. This was the most time I had spent with any of my co-workers. All in all it was a very nice day.

Monday evening I texted Sheryl, hoping to get together. We set a date for Wednesday. Pizza and a movie. There was a new one she really wanted to see. Sheryl was witty and bubbly. I was on my best behavior and just held hands.

"That was kind of a chick flick. Sorry," she apologized. "Let's go back to my place. We can find something better streaming on-line."

Sounded like a nice invite to me.

I'm not sure what movie we selected as we spent most of the next couple of hours just talking. I told her about my Rochester move and my new job. And the girlfriends I left behind. She married right out of college to a guy ten years older. A year later was divorced. Her husband was banging his boss's wife almost from the start. She got a nice settlement to keep quiet. That was a year ago.

"Oh, it's getting so late," she exclaimed as she got up from the sofa.

Time to go. It was a nice evening.

She took my hand and walked me into her bedroom.

"Six months without sex and I'm so horny. Please don't think badly of me.," she explained.

We made gentle love. I ate her pussy to climax and then fucked her.

"My husband was a bastard but a good lover. My first. Only one guy since and that was a mistake. My friends encourage me to get out, put my hurts behind me. I figured a Saturday afternoon date at the track would be rather safe. I'm glad we met."

"So am I. You are a very nice girl. And very attractive. I enjoyed making love to you. I hope you liked it as well."

"Oh, I did. You were as good as my husband at eating my pussy. And your cock is bigger. I like that.

"I hope you can understand. Ralph took my virginity. I thought he was my soulmate. I was devastated when I found out he was living a lie. The last year has been so hard. I'm not ready to have a relationship with someone. But I really like you."

"I understand. I currently see someone regularly. And yet I would also like to continue seeing you. No strings. Just friendship and some loving. Does that make sense to you?"

"Yes. Thanks for being so understanding."

We had several more dates. Sheryl was a sensitive lover and liked to make slow oral love to my cock. When I was about to burst she would gobble it down, taking all my cum in her throat. Then she would clean my cock with her tongue and play with my balls until my cock was ready again. She preferred being on top which I enjoyed very much. Our lovemaking was gentle and extended.

"John, I have something new to show you," she announced a couple of weeks later. "What do you think? I shaved it off."

Her newly bare pussy looked delicious. "I told my girlfriends about you and what a good pussy eater you were. They encouraged me to go bare and Masie volunteered to help me. We did it last night. Still a little red."

"I love it. Lots of girls are doing it, especially if their guys eat pussy. No stray hairs."

She spread her legs to show off. "See anything you like? I feel like I'm already dripping."

I brought her to climax in just minutes. She clamped my head between her legs as she came. "God, that was good. My friends were right, bare is better."

"Turn over, stick that sexy butt in the air." I positioned my cock at her hole and smoothly entered in one stroke. I fucked her for a solid ten minutes before shooting.

She turned onto her back and spread her legs. Her newly bare lips were engorged. My cum was already leaking out. Her pussy was so inviting I wanted to do her creampie but was not sure how she would react. Oh, well, give it a try.

I scooted down between her legs. "Sheryl, your pussy looks so sexy now," as I used a finger to slide between the lips. I stuck my tongue in and licked. She didn't say anything but soon started to hump her hips. "Oh my, John, that feels wonderful. Oh ... Damn!"

"Well, shaving my pussy was sure worth it!" she exclaimed a minute later as she hugged me. "And I thought my ex husband was good. You make me feel so sexy. Do guys really like doing that?"

"I do. Many guys wouldn't. Of course some guys won't eat pussy either. I think many women would be claim to be horrified."

"Well, you can do me any time you want!"

**********

The next several weeks settled into a satisfying routine. Cathy and Sheryl, alternating Fridays and Saturdays. Some fun times during the week. They knew of each other but hadn't met. Strikingly different personalities added variety. I liked them both.