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Sarah's Quest: Chapter Two

"Sarah's sexual adventures continue with an alternate lifestyle in unexpected places."

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Sarah is a wife and a mother of two. She has begun a search to clarify her sexual identity. In Chapter One, Sarah tested the waters looking at internet adult forums and participated in cyber sex. With a smorgasbord of sexual opportunities to consider , she is ready to embark on more intimate experiences.


The next day I decided to raise the bar. I didn't want to participate in more cyber sex which wasn't much better than masturbating to a porn flick. There is a small incremental step between porn videos and cyber sex. I craved the real human body. I read fetish posts, a few orgy stories, sexual role playing, and even BDSM on the Internet. By then, I had a pretty good idea what was out there.

It was during Monday Night Football when I asked Ted to watch the kids while I was out with the girls. He mumbled, "Have a nice time," and I was out the door.

I drove ten miles out of town to the nearest sports bar. I figured lots of guys would be there. It was time to see if a thirty-eight year old mother of two was still attractive enough to get a man's attention. I dressed seductively but not so much so that I looked like a whore. The bar was busy with young professionals and most of the guys and gals were glued to the TV. Everyone was ten or more years younger than I.

The game was in the second quarter when I found a seat next to a nicely dressed man about my age at the bar. We said, 'Hi', and I ordered a scotch and water, no ice. He didn't say much and to be honest, it was so noisy that having a conversation was out of the question. It quieted down at half time. By then I was on my third drink and Jason, the man with whom I was sitting, bought a round for both of us.

I learned he was a recently divorced dad of three, two girls and a boy. He was on a business trip and stopped in the sports bar for the game and company. He said he was at the bar because it wasn't very exciting watching a football game alone in a hotel room. By then, I was a little light headed and told him far too much about myself including my insecurities. Jason was a good listener and empathized with my situation. He held my hand and said that I was a beautiful woman and any man would be lucky to have me.

When the second half started, he said the noise was too much and asked if I'd like to join him at the hotel for a nightcap. I followed him to his hotel only five minutes away. By then it was pretty obvious what he had in mind and I guess in mine as well.

His hotel room had clothes scattered about and he apologized for the mess. He tried to pick up stuff to make it look a little more presentable, then poured us a glass of whisky from a flask in his suitcase. I hate whisky but took it to be polite. We started talking about our sex lives but I'm not sure how the subject came up. It might have been a comment he made about me having a sexy body.

I wanted to move things along so I asked, "What part of a woman's body do you like best?"

"Oh," he said. "I like your pretty face and of course you have nice looking breasts."

"Thank you, Jason. You're very kind to notice."

"Would you show them to me?"

I just sat on his bed sipping the whisky without responding. However, I gave him that 'maybe' look. I wanted to appear reluctant so that I didn't appear to be overly anxious to have sex.

He turned on the TV and dialed up a movie while we chatted. I was a little drunk and definitely horny. Jason was no different so it was no surprise he had chosen porn. More than watching two people fucking on the screen, it was the sounds that turned me on. The woman squealing and the man grunting got me into a frenzy.

The sex on the TV screen got us talking more explicitly about our needs. He hadn't had sex with a woman in six months and I admitted that having sex with him would exciting. We talked a little about our fantasies and eventually the time had come for him to undress me.

By the time Jason's pants hit the floor, I was naked on the bed ready for a much needed release.

Our foreplay wasn't anything special. He sucked my nipples and rubbed my pussy. I gave him a short blowjob. He licked my clit until the moisture in my pussy began trickling down toward my ass. I was ready for the first time to fuck someone other than my husband.

As his hard thick penis approached my vagina, he said my breasts were exquisite and I had the face of an angel. A girl needs to be reassured like that before being fucked by a stranger.

I responded by spreading my legs further apart as if to say, 'Engulf me with that stiff shaft. I want you inside me'. He read my mind slipping his well-endowed cock deep inside. Oh, what a beautiful sensation! His motion was slow and deliberate. I needed it a little rougher so I whispered, "Harder, Jason, harder!"

He responded by fucking me with an athletic energy. At that I took the bull by the horns, so to speak, and decided to try out a few tricks from Cosmopolitan. He was a willing partner. Most of the time I took the lead and we fucked in a bunch of the positions suggested in the article. We both enjoyed experimenting with the variety of ways a couple can copulate. I reached two orgasms before Jason gave out a groan that could only mean one thing, he was exploding with repeated spasms. His cum was gushing into my cunt in a way I had never seen or felt. God, this felt great!

Jason suggested we try anal. I said, "I don't know, Jason. I'm an anal virgin and the idea scares me."

"Well, Sarah, me too. I've never tried it and maybe this would be a good time for both of us to experiment."

My mind was still dazed by the whisky and the good fucking he gave me. Filled with lust I said, "Okay Jason, but be gentle."

Jason reached into his suitcase and brought out a travel size tube of Vaseline. Smearing the jelly on his cock seemed to improve its condition because his cock lengthened to a frightening size. I say, frightening, because it was hard to imagine it fitting in my ass. I took a little lube on my fingers and massaged his prick until he was fully hard. Still having some doubts, I sat on all fours allowing him to fit his greased fingers inside me. It took forever to get my sphincter to relax and we almost gave up.

"Sarah, let me try it. I think you are ready now."

So he did. Jason didn't fit easily. He poked his cock head in. I screamed. He was determined. Jason tried again. I cried out but not as loud this time. It hurt each time Jason inched in further until I knew he had succeeded in pushing balls deep into my rectum. Pain was now replaced by a very special new feeling.

Once Jason knew I was no longer in pain, he let his instincts take over and hammered relentlessly at my bottom. Meanwhile, I fingered my pussy and just lost all inhibitions. "Fuck, fuck, fuck," I yelled in the most unladylike way.

It took some time for Jason to cum but not me. My climax was intense followed by another orgasm that had me squirting for the first time. My moaning and screaming aroused him to a monstrous ejaculation. He shot jets of semen up my ass. He finished with powerful thrust and collapsed on top of me.

Afterward, I went to the bathroom to clean up, then dressed and began to leave. He said, "Sarah, you are a wonderful woman. Don't change a thing. My ex never allowed me to try the things we did tonight. You are my fantasy lover come true."

I said, "Ditto," and added, "The point is, Jason, we needed each other tonight. Thanks, I loved your company."

I drove home with a sore ass around one or one thirty that morning. Clearly, I was still sexy enough for men to want me so it was time to move on from this first encounter with added confidence.

Later in the week I received another message from Dylan. Dylan and I had been exchanging raunchy messages since I had posted my pictures on the sex website. He was a twenty year old drama student at our local college. Acting was his passion. Dylan thought I was sexy and suggested we get together and do a little role playing. Dylan had a fetish. He loved older women. He wrote that he had fucked his step-mother for most of his senior year in high school. He even tried to get a teacher in bed but that only earned him a two week suspension.

What he had in mind was for me to dress up like a whore and service him, maybe even make a video of it. I told him I would think about it but definitely no video.

Over the weekend he sent me pictures of some of the plays he was in along with some seriously lascivious photos. He was young and handsome so the whole idea began to interest me. Anyway, role playing was a fetish of mine and pretending to be a whore fit with my fantasies. On Monday, I agreed.

Dylan set it up when his roommate was out of town. I was to come to the dorm and take the elevator to his room on Saturday afternoon. He said I should be dressed like a prostitute and knock on dorm room number 347. When he asked who it was, I was to say, "The lady from Pleasure Escorts." Apparently Dylan liked to choreograph our encounter and make it realistic. I was turned on by the idea.

I found the trashiest clothes I owned and put on fuck heals and fishnet stockings. I drove to the college and found Dylan's dorm among a maze of university buildings. The elevator was empty except for a sweet girl who looked to be twelve but she said she was a liberal arts freshman. She asked me if I was there to visit my son or daughter. I said, "No," in a way that made it clear our conversation was over.

The dorm was huge so I wandered around before finding room 347. I knocked. He said, "Who is it?"

"The lady from Pleasure Escorts," I whispered seductively.

He opened the door and let me in.

Dylan had his shirt off wearing only a blue and white male thong, accentuating his genitals. I thought he had a football in there.

He said, "Take off your clothes, whore, and fuck me."

I told him how I dreamed of him fucking me and to treat me like a whore. I encouraged him to do what he wanted. Obviously we were on the same page! He obliged.

In no time I was naked, all except the fishnet stockings. I groped between his legs tugging at his thong. Dylan's cock sprung loose as soon as I pulled it down, revealing a very firm seven inches. At the head of his penis was a horseshoe shaped piercing and three pierced rings dangled from his balls. If I was wet before, I was soaking wet now.

We screwed in every creative position his imagination contrived and he had a keen imagination. Keeping my fishnet on but with the fullness of my boobs exposed, he ravaged my tits with his lips and teeth. The fishnet had a slit at my pussy so he had easy access whenever his cock was ready to be satisfied. The feeling of having a hard cock with jewelry attached sliding in the walls of my vagina was extraordinary. Toward the end, after he had already ejaculated once in my pussy and once down my throat, he asked me to do anal. I couldn't believe he could still get hard enough to fuck me again. I explained that prostitutes charge more for anal. He was cool with that.

He came prepared. My young stud pulled out a tube of K-Y Jelly from his backpack and ripped open my stockings. In a minute his prick and my ass were well greased, then he slid into me like a hot knife into butter. I was surprised at how easy it was this time. While Dylan banged into me, I played with my clit and our finale, like the final scene in a play, was spectacular! He spurted his cum deep into my bowels and I actually squirted with a thundering climax.

To make the role play appear to be more real, the young student shouted with a dramatic flare, "You're a great fuck bitch. Now get the hell out of here." I only had time to get dressed without fixing my hair or makeup. There were lots of curious looks before I got back to my car. The excitement of the afternoon was a monumental step forward to what I had been looking for!

The experience with Dylan should have satisfied my sexual urges. Honestly, I figured role playing was about as adventurous as I could tolerate. During the following weeks, I played the role of soccer mom and the good wife again. We did some family things like going to a circus and checked out the museum at our nearby university, hoping not to run into Dylan.

After awhile, boredom set in again and I got the itch to browse porn websites. I discovered tumblr blogs and that got me excited to try something new. As my excitement grew, I googled everything that came to mind. Some of the more interesting blogs were posted by swingers. Curious, I sent a few feeler messages out to people with whom I had corresponded. A girl sent me a link to a swingers site. I checked it out and there were parties in many locations throughout the country.

One was in my state and I sent an e-mail to the host to ask about it. They replied with the details indicating they were "all inclusive" meaning both couples and singles were welcome. It also meant this was a multi-racial club. The location was at a private home in the city four hours away by car. I made reservations by filling out a short survey asking for gender, race, age and so on. Ted was told I was meeting a girlfriend so he looked after the kids. I dressed in casual soccer mom clothes and checked into a nearby hotel mid afternoon.

The party wasn't until 8:00 PM so I shopped at the mall for a couple of hours.

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After dinner, I asked the hotel clerk for directions and showed up at the door as nervous as hell. I was actually shaking with nerves. A woman opened the door. She asked for my name and a security code they had given me online.

"Welcome, Sarah," she said with a friendly smile. "Everyone's at the bar. Introduce yourself."

People were drinking wine and mixed drinks with soft music playing in the background so I asked for a gin and tonic and started introducing myself to both the men and women. There were about a dozen people mostly in their forties and fifties. We all looked pretty much like a group at a PTA meeting except the women were dressed seductively showing more cleavage and thigh than might be expected at the PTA . Yet none of the women appeared to be what you would call slutty.

They all seemed to know each other so I felt uncomfortable being a newcomer, and I was younger. People wanted to know my name and what I did in life but never really pressed for personal information. There was one lady with huge voluptuous breasts that was having lots of fun joking around with a group of men. My ample boobs looked small compared to hers. She was probably the sexiest woman in the crowd and must have been very pretty twenty years ago.

The house had a large living room and a rec room downstairs. There were bedrooms upstairs and on the main floor. After awhile, people stopped mingling and began pairing up. I had no idea who came to the party with whom. You would see a couple going upstairs, then later that evening the same woman went upstairs with another man. Once I saw two men escort the woman with big boobs into a main floor bedroom. That is what I wanted but no one actually asked me to accompany them.

I wondered if I was expected to take the initiative. Not being escorted to a bedroom could have been because I was an unknown quantity or I was dressed too conservatively for the occasion. I was doubting myself again. Two stiff drinks fortified my confidence and I was ready to approach a man. He was a black man wearing clothes that were probably bought in the seventies. I started the conversation by asking, "Are you here with someone?"

"Yes, I'm here with my wife. She's upstairs with Jake and I'm trying to recover after being with that acrobatic lady, Tammy. She's a tiger in bed. You know her?"

"No, not really." I told him, "This is my first time here."

We introduced ourselves, then he said, "Would you like to dance?"

"Sure," I replied.

After a short waltz, he took my hand and led me downstairs to the rec room. Immediately we got down to business. He removed my blouse and skirt. I unhooked my bra. I was so horny by the ambiance at the party that my thong had a wet spot so it was evident there was no need for much foreplay.

I unbuckled his pants and pulled down his boxer shorts. He was still soft and obviously hadn't recovered from fucking acrobatic Tammy. I sucked his limp dick for several minutes until his cock firmed. He had a formidable fuck organ. His flaccid penis had concealed the truth about his growing erection. When he was hard, he was huge. The man's cock stood out like a full size salami sausage.

We started fucking on the pool table. Believe me, that was better than playing billiards. First I leaned against the table facing him. He pulled down my thong and tasted my feminine juices. My lover approved as he licked all around my vulva. "Delicious," he murmured.

With his strong arms, he sat me on the table and spread my legs apart. There I was lying spread eagle on a billiards table and behaving like a whore. Before stuffing me with his hard salami, my pool partner grabbed a cue and used the butt end to rub my clit. I was in such a frenzy that I yelled, "Stuff it in!" He misunderstood. I meant for him to start fucking me. Instead he eased the hardwood stick into my pussy. It slipped easily into my wetness and he worked it like a long dildo.

Finally, I begged him to stop. It was him I wanted inside me. He accommodated without further encouragement. The cue stick hit the ground at just about the same time he rammed into me, stretching my pussy to the point of being painful, yet a satisfying pain.

Soon, my lust overtook that early discomfort and I became accustomed to his size. There was no slow and leisurely fucking with this man. He pounded at me from the start. Rapid strokes gave me a tingly feeling and my wetness helped let his monster dick slip in and out with ease.

He turned me over with my feet on the floor and my elbows resting on the pool table. He helped himself to my swollen snatch fucking me from behind, grunting and groaning the whole time. My tits swung with each stroke and my nipples became enlarged and erect.

Before cumming inside me, his muscular arms turned me back around to face him with my arms around his neck. Quickly he picked me up pulling my legs around his waist. He eagerly plunged his greedy rod into me again. With me wrapped around him, I expected him to explode but he came without much of a flourish. Apparently, the tiger Tammy had taken a lot out of him.

I enjoyed each time he penetrated me as well as the different positions although I came only once. It was the first time I had a black cock inside me and it was amazing. No matter what they say, size matters. It was the first super size cock I had since the summer before college with Billy Joe. I got dressed and thanked the man for a wonderful time. We went back upstairs together as if nothing had happened.

The sex in the rec room had aroused me to a fever pitch. My hard nipples chafed against my bra exciting me even more. The anticipation of a man's lips sucking at them stimulated my brain into a fuck organ. I only could think of one thing, sex, sex, sex.

There were only two men and a woman left at the bar. As I sipped another drink, I got chatting with the guys wondering if everyone had left. They chuckled and said, 'no', everyone was busy upstairs.

The guy with a well trimmed beard asked, "Have you known Professor Jackson long?"

"Professor who?" I asked.

"Professor Jackson, the man you were with a few minutes ago."

"Oh no. We just met."

The clean shaven man commented that the Professor was a regular and popular with all the women. I found that easy to understand. It turns out he was a professor of African studies at the college near my house. "Oh my God!" I thought.

After a few more sips, I got up enough nerve to ask them something about protocol. "Do they normally allow threesomes here?"

They told me it happens but most of the ladies weren't into it. "Judy, the lady with the hooters does it but not many of the others," the bearded man said.

They asked me if I would like to join them in an upstairs bedroom. I pretended to be unsure and finally said, "It might be fun but please be gentle with me. This is my first time swinging and I've never been with two men."

We introduced ourselves while heading upstairs to an unoccupied bedroom. The men, Brad and Tyler, led me toward a nice quiet room with a king size bed. Brad was the bearded one. Both were in their mid to upper forties, nice looking, but not Hollywood handsome. I was politely undressed for a second time that night.

Tyler kissed me with a deep passionate kiss while Brad used his lips and tongue to caress my vulva, tasting leftovers from a half hour earlier. I could see his hard-on already bulging from his slacks.

Tyler eased me onto the bed fondling and sucking my tits. After watching his buddy sucking on my erect nipples, Brad stripped and joined us in bed. The three of us were stark naked and ready to play.

Moving to the head of the bed, Brad presented his pulsing erection to my mouth and I engulfed it on queue. Tyler 's cock found my cum enriched honey pot, taking no time to slam into me. I was sucking one guy while the other rammed into me providing a strange feeling of being in a dream.

The two men couldn't have been more different. Brad had a long thin penis while Tyler 's was shorter and thick but what was more fascinating than their cocks was Brad's balls. They seemed to hang nearly half way to his knees. They were both grotesque and inviting at the same time. I couldn't keep my hands off them while he was fucking my mouth.

They switched positions from time to time giving me a taste of each man. I had no trouble taking Tyler all the way down my throat but deep throating Brad was too much for me, especially since he had a large swollen head at the end of his prick.

After seeing these things in adult films, this was a fantasy being played out!

The two men were pretty much in charge, doing whatever appealed to them. I was getting a good fucking by different cocks and in different ways. What do they say? "Variety is the spice of life" and I was in ecstasy.

This went on until one of them suggested we try DP. I just nodded, 'okay'. It was something I had never done but wanted to try after reading a few comments posted on the Internet. Several women wrote that every girl should try it at least once. So I did.

I was on top of Tyler getting pussy fucked while Brad moved behind me. He pulled my ass cheeks apart and spit some saliva in my ass hole. The guy seemed to know what he was doing as he worked a couple of fingers into me until my anal ring relaxed. At first it was a bit of a jolt because he just slammed into me from behind. It was not unpleasant but unexpected. Brad hadn't wasted any time slipping his hard meat all the way inside my rectum. He worked his slender tool with the energy of a teenager while Tyler reamed my pussy. After all I reasoned, this was the third cock in my anus so, no harm no foul. I was just lucky that it was Brad doing my bottom, not Tyler 's fat cock.

They worked themselves into a frenzy thrusting exuberantly at my holes. All three of us had worked ourselves into sweaty steamy bodies. The slurping sounds of sex, the animal-like grunts of the men, me moaning and the smell of body fluids forced me to lose all pretense of being a proper lady. When reaching a powerful orgasm, I let out a scream that, frankly, scared the hell out of me. I was again getting the sexual adventure and satisfaction I had sought.

Brad and Tyler continued banging me for another ten or twenty minutes but it is hard to say when you are being impaled by two lustful men. When the guys finally exploded, they let loose with massive amounts of man juice. I had gotten a full service fucking, a double orgasm and some much needed attention for myself. I showed my gratitude embracing each of them as they dressed and were ready to leave the room. They returned hugs, then showed me into the bathroom.

I took my time there regaining a little composure and cleaning my private places. The mirror showed a happy lady with a rosy face and a very red behind. It was while looking at myself in the mirror that I began to realize that my escapades had left me vulnerable. Should they have used protection? I wasn't worried about getting pregnant because I was still on the pill but there was always a chance and there are other considerations when having intercourse with strangers. I hadn't fully thought that through.

Finally I left the bathroom only to see another couple on the bed already in the thick of passion. I stood there enjoying the moment until the man looked over and asked if I'd like to join them. I almost agreed but it was getting late. A threesome with a man and another woman would have to wait.

Brad stopped me at the door as I was leaving and said I was the sexiest woman at the party and as a hobby he occasionally made videos for adult Internet sites. He said he has videoed a few of the girls at work and he would be honored if I was one of them. I said, 'no', but he gave me his business card saying to contact him if I changed my mind. The card read, Brad Forsythe, CEO , and it was at the largest corporation in town. Surprise!

Tyler waved good-bye and yelled, "Now y'all be sure to come back and see us again soon."

I left the party far more satisfied than I had imagined but with my head spinning with questions. Had I gone too far with this? Was I cascading down a slippery slope? Had I become a slut like my classmate Kimberly or just a housewife looking for more in her life? Was this an obsession, an addiction? Shouldn't I be feeling guilty? How far do I go before calling it quits?

I was back at the motel around midnight . Okay, I felt a little slutty but it comes with the territory. Still, can a woman become addicted to sexual adventures and lose all sense of reason? When I undressed for bed, my panties were soaking wet with a mixture of juices that still oozed from between my legs. There was something almost obscene about it but stimulating.

On the way home the next morning, I did a lot of thinking. My thinking alternated between craving more sex and becoming the good wife. It was just before noon when I arrived home and had some explaining to do but it all worked out. No one expected I had been on an exploration of sexual awaking. Now, what would be next or should there even be a "next"?

(Sarah decides to break the mold and continue her adventures in Chapter Three.)

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Written by xhardx13
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