Friends With Benefits
Chapter 1: Oh What Stories We Do Tell
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Ma/ft, ft/ft, Consensual, Drunk/Drugged, BiSexual, Heterosexual, True Story, Cheating, Revenge, First, Safe Sex, Petting, Squirting, Voyeurism, Babysitter,
Desc: Erotica Sex Story: Chapter 1: Oh What Stories We Do Tell - Ann was my buddy Tom's girl friend. Ann decided I needed to get laid, so she introduced me to her women friends. Oh my! Thank you, Ann. Tom got envious of my seemingly never ending chain of bed mates. When Ann found out he had restless dick syndrome, she needed me to comfort her. We hugged and shared sexy stories with each other. Then we made our fantasies come true. Too bad for you Tom.
I met Tom through the college sailing club. It started off weird. We resemble each other, tall, blond hair, beards, lean muscles, liked to party and sail boats. At a club party, a female guest mistook me for Tom and started to give me a hard time. She said a blond guy with a beard groped her friend. Leaping to my defense one of my buddies said. "Hey, there's a guy here that looks like you." So it began. Not the best introduction.
Anyway, we met. Tom started to find reasons to meet up or visit with me. Lord knows he wasn't gay. Tom brought girls along like flies. His most frequent girlfriend, Ann often tagged along with him. As to the groping incident, Tom said, "It couldn't have been me. I was with Ann at the party." As it turned out later, it probably was him.
Tom tried to ingratiate himself with me by volunteering to help me with projects like boat and car repairs. He wasn't very handy, mostly useful for extra muscle which came in handy if you needed to move something. It was Ann who I really hit it off with intellectually. We could talk for hours. When my housemates graduated and split for Alaska and California, Tom tried to fill the space. I had sized him up as a tolerable party jerk ass but not someone I'd want to share my house. So I moved in with other friends and Tom wound up in a lease somewhere else. I breathed a sigh of relief.
My new place landed me back in familiar shabby hillbilly slum elegance, next door to where I used to live. I shared a three bedroom townhouse with two close friends, a girl/guy couple who had just graduated. I'm still in grad school. Marci was teaching special-Ed in an inner city school. (Read – she deserved combat pay.) Dan had a job as an industrial sales rep. We were all trying to live cheap and save money.
The townhouse was quite fancy one hundred years ago. Now the perfect 1890's neighborhood had gone downhill. Way downhill. On this block there are two rows of townhouses with original woodwork, kitchens, wiring and furnaces. With our landlord, it's do it yourself maintenance and decorating, but the rent is very low. Fantastically cheap split three ways.
Before we moved in, we sanded and varnished the floors, repaired plaster, painted walls, repaired windows to fit tight and tuned the furnace for better performance. Tom volunteered to help. We even added a window box fan over the furnace return register so the hundred year old monster gravity furnace had a make-do forced air heat. Outside it's a slum. Inside, pretty nice.
We joked about the neighborhood being so poor; we were the only house on the street with a book. No one had anything to steal, so the neighborhood was pretty safe.
Nine months later, my new place had a big vacancy. When the school year ended Marci and Dan split for San Francisco. This time Tom suggested that Ann take the open bedroom in my hillbilly heaven townhouse. I didn't have any illusion that I was gaining a girlfriend. Ann was just another of a long line of female housemates for me. Some had been lovers, most of them had not. Their sisterhood had educated me about women at many levels, introducing me to many of my intimate female friends. Truth is, women know women and will introduce a good guy to their friends. Ann had already fixed me up with a series of her friends. Many of Ann's friends wound up in my bed. It was just Tom's girlfriend introducing her friends. Friends helping friends. Right?
Over the time I'd known Tom, Ann and I had built a friendship. We found many things to talk about. We both enjoyed trips into the woods. I knew the local geography, Ann knew the local botany. But we were just arranging group outings. After all she was Tom's girlfriend. Wasn't she?
It was OK. At least I told myself that. Most of my friends think I'm just a hippy stoner engineer. A nerd. They see me fixing stuff so it runs well. That's really just a cover.
Ann knew, I'm really a suffering romantic with after-burn from the disastrous end of an intense relationship. The breakup left me feeling like a failure at love. I tried starting simply nurturing a house plant. Plants were Ann's thing. I asked her to keep her hands off my plant; I wanted to care for it. She asked why. I said. "How can I expect to be able to keep love alive, if I can't even keep a plant alive?"
Ann hugged me for the longest time and said, "Dave, you deserve to be happy."
I guess she likes me. It's OK even though she is Tom's girlfriend. Yeah, it's OK. I tell that to myself, often.
So I sublimated my hunger for love into rebuilding a wreck of an old Schwinn bike. Now I ride it to class. I keep my twenty plus year old Cadillac and Ann's wreck of a car running fine. I focused some of my frustration into exercise. Now I do a hundred sit-ups and fifty pushups every couple of hours as a break while studying. I can even do a horizontal plank handstand.
Despite Ann's efforts with introductions to women, I'm not getting past just hanging out with friends. Some of those friends happen to be women. A number became intimates, just not serious romances. I do take time to say, "Thanks, Ann." I guess she does want me to be happy.
Ann's not a classic beauty, but she is sexy. A five foot two red head with long curly tresses. She has never been skinny, never been fat, just a regular small town girl making it in the big city. She is wide hipped and small breasted. I've never known her to wear a bra or shave her body; she has a distinctly feminist earth mother attitude. Her Irish heritage splashes freckles across her pale face and shoulders even in the dead of winter. Why is she sexy? Well, she just loves sex. Sexy seems to come out of her pores. I can hear her happy fuck cries through the walls of our house. She makes me crazy. So I just call one of her friends and make noise in my room. Just trying to stay happy.
Neither of us was ever very body conscious around the house. We had both seen each other naked. An 'oops sorry' kind of walk into the bath on each other. A flashed naked beaver under a long t-shirt. Dick and balls hanging out of gym shorts. I knew her little tits had just a little crease underneath, not a fold. Thinking about her made me stiffen. Kind of like siblings. Horny fucking siblings. We went group skinny dipping with Tom and some others at a farm pond way out in a cornfield. It was just fun, squishy mud bottom, friendly fish nibbling, cooling off on a hot day, no sex fun.
If Ann isn't fucking she thinks about sex. How do I know? Whenever she can, she talks about sex. She encourages other people to have sex with each other. How do I know? She sets me up to fuck her women friends. She gets naked as often as she can. It's OK, she's just comfortable around me or so I thought. After all she was Tom's girlfriend. Wasn't she?
The daughter of a doctor, Ann got the birds and the bees details at an early age. Daddy gave her condoms, taught her to be careful. With her parents approval she has been happily sexually active from her early teen years. For her sixteenth birthday she got a car and an IUD. She likes sex.
Somewhere along the way, Tom decided some fresh pussy was just what he needed. Maybe it was watching the line of Ann's women friends moving through my bedroom. Maybe it was just restless dick syndrome. Anyway, Ann retaliated by upping her own quest for new dick. Now Ann and I are both dating, but not each other. I have plenty of women friends in my bed. Interestingly, Ann made sure my dance card was full.
Sometimes Tom's orbit swung close around Ann, but more often he's off chasing strange new pussy. One evening, Tom came by saying he wanted to talk with me. Ann wasn't home, so the two of us settled in for a talk. Tom seemed to be going nuts with not knowing where Ann was. I got a text from her, "saw t car no wan see t txt me wn gone." I told Tom it was Ann. She was going to be late if she came home at all. We drank some beers and Tom paced. I felt a devilish satisfaction by vexing him. I realized, I like Ann a lot more than Tom. Between hits he admitted his hunt for casual pussy wasn't going well. He asked enviously how I met so many women.
"The answer's simple. Ann. Without her making introductions it would be a lot harder. I swear, good women friends introduce you to their women friends." I got another text from Ann asking if he was still there. I tell Tom, she's not coming home tonight. Before too long he heads out to continue his frustrated pussy quest. I realize he was hoping to tap her that evening. I text her back saying, "t gone." Minutes later she came through the door.
She took a seat straddling my lap and began to interrogate me about my visit with Tom. She beat me into submission with her boobs, snuggling into my arms before I came clean. I told her of Tom's frustrated pussy quest. That got her giggling and snuggling even more. My dick threatened to burst through my jeans. Her hot panty covered pussy took my measure. I told her, I was thankful she is my friend. Especially introducing me to her friends. We wound up necking, groping each other and kissing. We stayed fully dressed but we were necking like naive high school kids. Then we went to bed alone. Yes, I did hear the sound of her orgasm through the walls. I don't know if she heard me grunt as I was shooting mine.
Ann was getting plenty of sex, just on her own terms, which occasionally included Tom. She brought a steady stream of lovers in overnight. Sometimes she stayed away for days. Sex was a frequent subject of Ann's conversations. Her sexy talk hooked guy's attention like nothing else.
She wanted to know all about everyone's sex life. She asked questions and demanded details. There was no 'what happens behind closed doors stays behind closed doors' with Ann. In a noisy bar she would ask a stranger in a loud voice, "Do you like to fuck?"
If they didn't run away, she would ask, "How old were you when you lost your virginity? How was it? Did you like it? Who'd you fuck?" It didn't matter male or female. She could work a crowd into a frenzy. It sounded like a porn interview. On a roll, she would ask, "When did you last have sex?" Then follow up with, "How often do you masturbate?" How did I know about this? Well, she had pumped me with all the same questions right in front of Tom. I'd seen her work people at parties too.
In a big crowd she just asked for simple facts. She definitely worked the shock factor, way beyond Howard Stern or Amy Schumer. With friends she wanted every freaking intimate detail. One on one the questioning can be intense; "How many different people have you fucked in a day? Have you done it with more than one person at a time? What makes you orgasm fastest? What was your best fuck? Tell me what it feels like when you cum. Who do you want to fuck? How big is your dick? Really? Can I see? How big are your tits? Really? Can I see? Ever done girl/girl or guy/guy? Do you want to?
Ann and I tell each other it is alright. It is all right, isn't it? After all she wasn't my girlfriend, was she? But she does use me as cover if her sexy talk attracts a creep that she wants to ditch. I'm willing to be used. Come on, use me.
She retells the best of those personal stories to get your motor running. All the sexy talk is fun for her.
Yet ... It makes each of us crazy with lust for the other when the one of us has a sex partner in the house. We say it's fine. It's not fine. No matter what we say, there is a certain tension caused when the sounds of sex with someone else came through the walls. In fact it made us both fucking crazy to hear the other in the act. She admitted the sound of someone else having sex with me made her very wet. Ann's iron bed frame smacking the wall got me green eyed jealous, even when I had a woman slicking my dick. In fact, it's more crazy when we are both fucking someone else together. Despite this, Ann still introduced me to her female friends. She often whispered something in my lover's ears that led to a noisy night. Our bedrooms had never been so busy.
Then one Sunday evening, just the two of us were alone at home smoking an after study, before bed doobie. It was a bit strange. It happened to be one of those rare sexual dry spots. We were both facing empty beds, without one of our frequent lovers. Ann was pissed off at Tom and had been venting.
Changing the subject, Ann coaxed and prodded me to tell a sexy story about my past love life. Ann sat close beside me as she pressed the interrogation. She demanded, "Tell me a sexy story. Get me fired up so I can go rub off." As the story progressed, she rolled onto me blatantly humping her hot pussy mound against my leg. I gave her a weird look asking, "What's going on?" Ann replied, "I'm horny and frustrated with Tom. You are going to tell me a hot story, and then I'm going to an empty bed. I want to rub my pussy right now, but I'm going to settle for humping your sexy leg until I get into bed. Now tell me the fucking story." With that she settled against me with her tits smashed to my side and thigh mashing my rigid cock.
Settled in with a friendly warm pussy pressed to my thigh and my hand on her ass I began the story, "It was a dark and stormy night and the mate said to the Captain, 'Tell us a story Captain, ' and this is the story. It was a dark and stormy night ... OOWW." She bit me on the pec where she had been snuggled.
"OK, OK, My first lover was older but wiser. She trained me well and rewarded good performance. She liked women too and got me in a threesome with her housemate." Ann kept me talking with tit pressing dick groping foreplay. That was enough to keep us both hot and squirming. I continued to tell her, "Susan took me to show and tell. There were six women in her 'Our Bodies Ourselves' reading group. They had examined each other very closely. They even rubbed each other off. They wanted to check out a man the same way. I was up for it if we all got naked too. We all got naked together for an hour. Six women twisted and turned me every which way. I got to see deep inside a cunt spread with a speculum." The story went on quite a while... (See: A Willing Accomplice - Show and Tell Comparative Anatomy)
When I finished, Ann ran off to her room saying, "I've got to rub off." She left me behind to drop my own trou and frantically beat my own meat. We could hear each other pounding out a personal orgasmic rhythm through the walls. I thought to myself as my self-driven orgasm approached, 'We're making each other crazy. We aren't fucking each other. We're just friends. She's Tom's girlfriend, isn't she? UhUHahhh, sheesh, ' I came a ton. The jism shot up all over my chest and hand. In the quiet after my orgasm, I could hear the hum of a vibrator upstairs. Then I heard a series of the quiet whimpering female cries that had made me crazy so many times before.
I stepped out of my cum covered pants, used my underwear to clean up, and then headed upstairs to my own empty bed. After a pit-stop in the bathroom I passed by Ann's room listening for the vibratory humm.
Through the wall she called, "I had fun tonight. Thanks for the story. I hope it was good for you too." Her 'too' collapsed into embarrassed giggles of joy.
A few evenings later it was unseasonably warm. After our study hours were over, we sat together on the couch. It was odd for us to be so many days in a row without overnight bed mates. Was it on purpose? In the evening's heat, she wore a short denim skirt, I was in gym shorts. Both of us wore just t-shirts on top. As we passed a cold quart of beer back and forth, she coaxed me to tell another story. I said, "Oh no, I told you one, it's your turn. Now make sure it's something you really did, don't tell me somebody else's story or a fantasy. I want the real deal."
She frowned as she stared me in the eye. Then she pushed me over so I lay with my head up on the arm of the couch. She climbed on to sit pussy straddled right on top of my dick. Her short denim skirt bunched up around her waist. "Alright, I got one that will make me cream all over your pants. It's something that happened when I babysit, but not what you expect." Before she began, she kissed me with a smokin' hot, long lasting kiss.
Coming up for air, she said, "You told me you fucked two women. I never told you, but I fucked two women too."
I gave her a wide eyed, head cocked look. "Ummmhh?" I whined inquiringly.
She settled down against my body and began. "Back home in ninth grade I started to baby sit. Mostly it was for the same two kids, two neighbor girls. Different families, but I often watched both at the same time. The girls had lived next door to each other and grown up together. Their parents were friends, they were friends. When their parents went out, it was natural for me to sit with both of them, they would sleep over and I'd stay the night."
"Over the years, I watched them during the summer and had more sleepover supervision. Sometimes we camped in my tree house. It was a great job, we're friends, we had fun." Ann pulled my hands to her tits, as an open invitation to get groped. I started to work effleurage around her popped up nipples.
"At first we just played games, I gave them baths and got them ready for bed. We watched movies, scenes with kissing got 'ookie' reactions from the girls. I was fucking my next door neighbor every couple of days. I liked dick. I was all smiley with the kissing scenes. The girls didn't notice." Ann rolled her hips on my boner. Her little denim skirt rucked up over her ass to make a perfect place for my hands. Her panty covered crotch was wet and spread her sexy aroma over my dick.
"Then they started to bloomin' boobies and things changed. Kissing scenes were good. They wanted to kiss boys, but they really didn't have a chance. Boys their age were pretty immature. Older guys were big and scary. Their choices sucked, so I suggested we practice with each other. I started kissing fourteen year old girls, when I was a very worldly seventeen. We talked about sex and sexy feelings."
"They heard their moms talking about an older boy from church. Had to watch him. He was after way more than stinky finger. They wanted to know, 'What's stinky finger? What did she mean?' I showed 'em my stinky finger technique."
"I told them about making babies and birth control. We took off our clothes and looked at our holes. Didn't do much touching, just looking. They were afraid of making babies if I touched them, afraid of getting in trouble. I explained the sperm and the egg business. Let them know they were safe with me and each other. It's dicks that get you in trouble. They asked me if I'd had sex. I couldn't lie. I told them I loved it. I told them how I'd started fucking when I was their age. I would have been pregnant if Dad hadn't given me condoms. I felt it was my duty; their moms weren't going to teach them about sex like my parents did. I told them about masturbation, how a clit was god's gift to women." Meanwhile she was rubbing her gift against mine.
"An older neighbor girl got pregnant and the family moved away. There was a lot of speculation about who was the daddy? Might have been her daddy? You mean he ... what? OOOH."
"That summer, we camped out in my tree house, I got down to go to the bathroom. When I came back they were kissing, naked. I got naked too. We kissed and rubbed each other off. I asked if they put fingers inside or just rubbed clits. 'We don't do stinky finger' said Beth. You like to rub off, right? Stinky finger is too good to pass up. Specially if someone does it for you. We sucked titties and clitties. They had little boobies. Just a mouth full. You would love to suck their nipples. They don't have much hair and those little clitties are even better." She had my shorts covered cock lined up between her panty covered pussy lips. I could smell her excitement and feel her wetness soak my shorts.
"It wasn't the last time. I like their cunts too much. I licked two eighteen year old women the last time I went home." She rolled off to lie beside me blatantly stroking my pants covered cock.
"Got me hot," said Ann, "You need to go do something about that." She said, caressing my boner, laughing. Then she said, "I'm going to bed. You should go to bed too." Our mutual masturbation was just as frenzied as before. I was thinking about her. She was thinking about me. We weren't going to cheat. She was Tom's girlfriend, wasn't she? Oh, maybe not.
The next night was Wednesday; we both went out to the sailing club meeting. Ann disappeared to stay overnight with someone. Never said boo to me, just disappeared. I figured she was getting her horns trimmed. That thought would have made me green eyed jealous, except I was busy fucking one of the sailing club cuties. She had been around, but not around my dick. Evidently someone had given her a good word. The evening started with me asking her if she wanted to drink beer or get out of the bar with me. I told her, "I think there is a dark and stormy night coming on." She said, "Really; I thought it was clear outside."
"Nah, not that kind, I feel a fuck storm in the wind. You feel it?"
She smiled shyly, but knowingly and said, "Maybe we ought to find shelter to ride it out. Is it very far to your place?" Inside of 20 minutes the storm was on us. She whipped it all over my dick. It stormed til after midnight, we crashed until morning. Then there was another early morning storm. From the sound of her she enjoyed herself. It was mutually very satisfying.