Sarah’s First Time–at 19

Her big sister's boyfriend does Sarah – Part I

Sarah's "first time" sex story that she finally told me was more than a little surprising and very entertaining...and much more memorable than my first time. Perhaps a harbinger of her sexual re-awakening many years later.

As mentioned previously (sorry for the long story hiatus), my wife Sarah has become a lot more sexually alive and open-minded in her 40's. We're both now much more explicit about what we like and would like to try, sexually, and we love telling stories to one another about past sexual adventures and fantasies. Best of all we are enjoying sexual activities that I'd never dreamed my wife would even consider...

At age 19 Sarah was an unquestionably attractive but long-legged, gangly sort of girl and really, a tomboy type at heart. Recently though, she had started to model a bit which her mom thought would help her self-confidence, and it did, eventually. Still, the boys in her high school hadn't ever seemed too interested, and she rarely dated and had never had a "serious" boyfriend by the time she graduated.

Other than being felt up, awkwardly at best, a few times by a couple "geeks", she'd never had any real sexual experiences and was still a virgin, but one who was thinking a lot more often about sex at age 19.

That contrasted with her "big" sister, Stephanie, who was three years older than Sarah. Stephanie had always had a boyfriend for as long as Sarah could remember...probably since she was 14 or 15.....and had dozens of them over the years. They came and went like the breeze. Guys had always loved Stephanie and her killer, hot little body. She not only had had a very pretty face (although not awesome as her sister), but also some other stunning assets: her tits and her little round ass and incredibly cute, curvaceous figure that she did her best to show off in any outfit that she wore.

Stephanie was maybe 5'5," and her younger sister towered over her from age 13 on. Statuesque, blonde Sarah at 5'11", though, had itty-bitty titties, especially compared to Stephanie's perfectly formed 34C's and none of the womanly curves that her super-popular sister did. Sarah said that boys and men of all ages could not help but gawk when they caught a glimpse of Stephanie in her array of skimpy bikinis went they went to the pool or the beach. At age 19 Sarah wondered if any hot guys would ever start looking at her the lusty way they ogled her big sister.

I had little trouble believing that my sister-in-law, Stephanie, had been a serious hottie when younger. A blonde like her "little" sister, she still has a beautiful face and complexion, and although she has put on a few extra pounds over the years remains quite attractive. Plus, her impressive tits have grown now to 35D's (which Sarah has confirmed). I'm mainly a leg guy, but admittedly, I've fantasized more than once over the years about getting to see Stephanie's impressive breasts, sliding my dick between them and shooting cum all over those puppies. Or maybe have her bounce up and down on my cock while I played with her substantial boobs that undoubtedly have big suckable nipples as well. It would be fun, no doubt.

As Sarah told her story, I interjected, "And so did Stephanie let any of her many boyfriends actually fuck her?" Sarah told me that probably at that point in time maybe a half dozen guys had actually gotten the privilege to get into Stephanie's panties and have sex with her, but she continued, "Of course that was a half dozen more than me, and Stephanie could have fucked dozens if she'd wanted to. She virtually always dated guys who were a few years or more older...and almost never guys her own age. Stephanie did tell me that the older guys were a lot better at sex than the young "boys."

Sarah and Stephanie had a sisterly "blood pact" about not telling ANY sex stuff (about each other) to their parents or others (unless authorized). Even though the two disagreed on lots of things and feuded on and off, they were very close sisters and friends – and agreed to never ever divulge anything about each others' sex lives. They also agreed to cover for one another if possible at all times. Of course, that had been pretty one-sided so far ...with Sarah knowing a lot about her sister's sexual escapades and having to confirm more than a few of Stephanie's fibs to their parents.

Unfortunately, there was nothing for Stephanie to really know about Sarah's sex life... which Sarah thought was pretty pathetic. Sarah's clueless parents thought that they had two angelic, virgin daughters still, but were only right on one account. Stephanie had first gotten laid when she was 16 by a college guy. And she told Sarah that she loved it.

Sarah continued her first-time sex story. It was the summer after she graduated from high school and was still living at home and had a couple part-time summer jobs before starting college in the fall. Stephanie was in college in the same town and had been living in an apartment with a two other girls, but their lease ran out and she was back living at home for a couple months until she got another place to live. This definitely cramped Stephanie's style at that point in time...being back under the watchful eyes of Mom and Dad.

It was strictly forbidden to have guys over to the house when her parents were not around...other than to get picked up for a date. One weekend that hot, muggy summer, though, her parents drove to visit friends out of town, leaving their lovely girls at home, unchaperoned for the weekend.

At that time Stephanie had a relatively new boyfriend, Danny, who Sarah thought was maybe the best looking guy Stephanie had ever dated and one of the looking guys Sarah had ever laid eyes on. Her sister always went for the tall handsome types. Sarah described Danny as a serious hunk: about 6'2," jet black hair and blue eyes, and built like a stud athlete (which apparently he'd been in college). Danny was also incredibly charming and had some kind of sales job with a big company and drove a BMW, too.

Sarah admitted that back when she was about 19 that she'd started to masturbate on a regular basis and often fantasized about Stephanie's boyfriends and other guys: what it would be like to kiss them and have their hands on her tits and her pussy and be able to touch and feel their dicks inside her cunt.

I asked my lovely wife how she liked to masturbate back when she was a late teen. This conversation was getting my cock rock hard as I listened...which was the whole point of us trading these stories: some additional foreplay to get things really going white hot, sexually.

Sarah told me that it was often alone in the dark under the covers in her bed at night when she'd rub her crotch under her pj's and end up finger fucking herself...often for 20 or 30 minutes or more. But if she knew no one was around in the house, she'd sometimes take off her skirt or shorts or pants and her panty and stand in front of her bathroom mirror spreading her long legs and very slowly massage her fuzzy, blonde pubic mound, and stroke the full length of her pussy lips and watch them get pink and swell in the mirror, and then insert a finger or two of one hand into her cunt while she diddled her clit with the other hand.

She liked to play and watch in the mirror until she made herself climax at least once or twice. Yes, she admitted that she had discovered her "love button" and found (her sister and a couple close friends confided to her) that it was the true secret to having "getting off" and having good orgasms.

Imagining my wife at the tender age of 19 watching herself masturbate in her bathroom mirror had gotten me rock hard (actually I have beat off a few times looking at her old teen modeling pics...including one swimsuit shot that clearly shows her right nipple when I digitized it from an old black & white photo). I asked Sarah if she'd show me what she did back then to get herself hot and bothered. She smiled, and told me to follow her to our master bath.

Lovely Sarah, who remains in awesome shape (and gets hit on often by guys of virtually all ages), slipped off her skin-tight jeans (and was not wearing a panty), and stood tall before our bathroom mirror with her long legs spread. She was in no rush as she enjoyed re-enacting her favorite masturbation adventures from long ago by rubbing her blonde bush, stroking her labia and then fingering her juicy opening and impressive clit. She fucked herself with one finger and then a couple. I watched her both in the mirror and from the side...she just loved to tease me by letting watch her masturbate. After several minutes of playtime Sarah was dripping and moaning that she was cumming BIG.

I told Sarah to sit on the vanity as I freed my erection. I just had to fuck her. She jokingly protested, "Well this is a little off script...but OK." She told me, "I do remember sitting like this on my vanity at my home a couple time and masturbating: imagining that a handsome guy like you was sticking his dick in me. " I spread my wife's long legs more, stood between them and rammed my full shaft up into her slippery twat and began pumping her pussy. After a few minutes of frontal fucking while Sarah played with her slit and clit as my dick dove in and out, she told me she wanted it from behind.

Sarah turned sideways in the mirror and braced herself on the edge of the vanity and wall, reached between her legs and guided my penis back inside her slick pussy. My hands on her bare buns I banged away while we both watched the action in the bathroom mirror.

As I fucked her standing from behind, it reminded me of a time several years before. We were renting a condo in Destin and one evening went out for some balcony sex which Sarah has always loved – and me too! She wore only a sexy little white top that was designed not to hide her pussy. First we fucked standing, facinge each other, as she braced one foot on the side wall and her buns against the 2nd floor railing. Then we switched positions, and she held on to railing looking out over a pond on the edge of a golf course, I and plunged into her pussy from the backside.

There were some outdoor lights at the condo, and apparently we were more visible than we thought. A car drove by on the other side of the pond, slowed down a bit, and honked in appreciation as I banged Sarah from behind on the balcony. We both chuckled and I waved at the car while I continued to pound her from behind.

We both watched my penis penetrate her pussy in the bathroom mirror. Sarah told me she wanted to see it cum out. I was close to firing, and so I pulled out of her cunt and jerked my shaft. She watched in the mirror as my cum shot over her crack and bare buns. I used it as lubrication, thumb fucking her asshole with and finger fucking her wet pussy my middle finger – until she moaned, "I'm cumming baby, I'm cumming so BIG."

Sarah took a quick shower and she got into sexy, sheer peach lingerie outfit before starting her first-time story again. "Where was I? She inquired," before you got so very, very naughty with me in the bathroom?" Sarah returned to her first-time sex story.

It was a blistering hot summer afternoon years ago, and Sarah was off work and just watching some TV inside. There was a knock on the door and it was Stephanie's relatively new boyfriend, Danny. On the front step, he said,"I'm here to pick up Steph to play some tennis." Apparently her very cute, very sexy, very smart but sometimes, air-headed sister had either forgotten to tell Danny or had left a late phone message (in the days before cell phones) that she'd be home at 5:00PM (which is what she'd told Sarah) instead of 3:30PM which is what she'd told Danny.

Even though it was sort of contrary to "house" rules, Sarah told Danny that he could come in...and if he wanted...and he could make himself at home. Danny said that he really didn't want to drive all the way back to his place and then back again, and so he'd thanked her and said he'd like to come in and hang out until Stephanie got home if that was OK. He thanked her and came into the house.

Sarah told me that she realized that she did not have much on (since she wasn't expecting any guests): only a little sleeveless top with no bra and some very short shorts with no panty (Sarah has always believed that a panty is optional female attire) and no shoes.

She remembers Danny staring at her, smiling. He said, she recalls, "You and your sister are two very beautiful young ladies." Sarah knows that she must have blushed crimson as she mumbled, "Thank you." Sarah invited Danny to sit anywhere he wanted and make himself at home. She went and got Danny and herself Coke's and returned to see him sitting comfortably on the big living room couch.

Sarah confesses that she doesn't quite know what possessed her, but when she came back into the living room (and could have sat almost anywhere she wanted); she plopped down on the other end of the big couch from Danny. He was gorgeous and very charming and made fun small talk for a while. Offhandedly, she mentioned that her folks were out of town for a couple days, and so it was Stephanie and her.

At one point in the conversation he asked how tall she was and remarked how spectacular her long tan legs looked...and then started talking about a former girl friend of his who was a masseuse, and she'd taught him to do great foot massages.

Danny asked Sarah if she'd like him to massage her bare feet. She thought for a moment then stretched her long bare legs out toward Danny as she lay on the big sofa. He took that as a "yes" and then started rubbing her toes and feet like she'd never felt before. Danny massaged her feet for several minutes...but then without asking he was rubbing her calves...and then her tanned thighs. Sarah did not protest. As he touched the inside of her bare thighs with his big, strong hands she could feel herself begin to get wet.

Sarah was looking for love but at that point was mainly looking to get laid by a hot guy....and more than a bit tired of always staying when her sister always had a date and always hearing about her sister's sex exploits – and those of some of her "experienced" friends. She didn't think that it was fair that it was so easy for her big sister to get almost any guy's attention. Obviously, her sister would not approve (of the present situation), and she felt a twinge of guilt for what she realized might now happen with Stephanie's boyfriend. Quickly, Sarah rationalized that feeling with the knowledge that her big sister would have plenty more guys after Danny.

Everything, Sarah explained, sort of went into a time warp for her as Danny's fingers lightly grazed her crotch through her shorts. Then his fingers were under her short shorts and he was touching her bush and slit, and she was definitely getting very juicy now.

Soon her little shorts and top were magically off, and Sarah was completely nude on her own living room couch. Danny was kissing her lips, his tongue was in her mouth, he was fondling her small breasts and touching her buns and excited labia. Then, as she lay back on the big couch, he shifted back down and was kissing her feet and slowly licking his way up her long, tan legs, inside her slender tanned thighs...

Danny spread her legs wide on the big couch, her pretty teen pussy gushing, and put his handsome head between her thighs. Sarah could not believe this was happening. One of her more sexually experienced friends had told her about oral sex and how much she liked her pussy being licked. Sarah could not relate when she first heard this but was now starting to understand why her girl friend enjoyed it so much.

Danny pushed Sarah's swollen pink lips apart with both hands and sucked her clit and snaked his tongue in and out of her virgin twat, then he was fingering her, and then more sucking and licking. His tongue danced in her cunt for quite some time, and Sarah remembers having an orgasm or two. She was in heaven with her sister's boyfriend's tongue exploring her dripping twat and never dreamed that she could feel like that.

Visualizing another guy lick my wife's cunt (especially when she was 19-year-old virgin) was getting me very hard once again. Sarah noticed the new bulge in my boxers and told me, "But of course, you are THE maestro of pussy eating, baby. I might let you lick me now." Sarah pulled off her thong and started fingering her slit. I got off the porch sofa and kneeled between her long, still gorgeous legs and watched up close and personal as she masturbated once again. Sarah opened her puffy, pink cunt lips for me with both hands and I dove my long tongue deep into her tasty vagina – and licked her for quite some time...until I heard her announce, "I'm cumming BIG, baby. Oh, I'm cumming so BIG!"

I badly wanted to stick my dick in my lovely wife's pussy again, but instead asked her to continue her story. I was really curious to hear what was going to happen next, and so Sarah resumed her first-time sex tale.

Sarah could not help but notice that Danny was very rigid at his crotch (and so was I listening to her story). He told that Sarah that she was so beautiful, and he loved the taste of her pussy. Then he told Sarah that he'd really like to fuck her, too, but only if that was OK with her. He was already removing his white tennis shoes, white socks, white shirt and then white tennis shorts and white undies and stood entirely nude next to the couch with his clothes and hers littering the carpet. She remembers thinking that if her clean-freak mom saw this kind of mess in her pristine living room (besides the sex) she'd go berserk.

She said that Danny looked like an Adonis: tall with a chiseled, tanned body and a hairy, but not too hairy, chest and thick patch of dark pubic hair at his crotch. Plus he had a huge dick that was fully erect, pointing upward. Before she could say anything he reached down in his shorts on the floor for his wallet and told Sarah that he had "protection." Deftly, he unwrapped and fitted the condom onto his erection which was now close enough that she could reach up and touch it.

How could she say no? She had imagined it for a long time now, especially after having experienced his talented tongue in her twat, and now wanted to feel a dick inside her – yes, even if it was Stephanie's boyfriend. Sarah could not resist. Although she wasn't exactly sure how Danny's large stiff penis was going to fit into her little virgin love hole, Sarah said "OK." Danny smiled, not looking too surprised that she'd given him the go ahead.

She lay on her back, naked on her living room couch (Sarah admitted she had no idea what would happen next) as Danny knelt between her long, slender legs and lifted one leg up under her knee like it weighed no more than a feather...then held his firm shaft and directed the swollen purple tip of his penis between her still excited lips. He inched his way deeper and deeper inside her as he lifted up her other leg – now holding both of Sarah's legs under her knees as he knelt between them and looked down on her, his hard cock now completely impaled in Sarah's no-longer-virgin vagina.

"Do you like that?" he asked her, and she told him, "Oh, yes, I love your cock inside me. Please fuck me more," she told him (wanting to at least sound experienced). In this position she could get a great view of Danny's face and gorgeous upper torso and arms and see his cock begin to slide in and out of her.

Sarah interrupted her story to mention, "There's one other guy who, the first time he fucked me, used this position." That would be me. Sarah and I met at our apartment complex nearly 20 years ago and started dating some, but she had a boyfriend who she wanted to cut loose but couldn't seem to do it (but whom she admitted to me later was fucking her a lot still). Finally, one evening, she called and said she had a big surprise for me and was coming over.