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My First Time

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I knew it was a bad idea from the start.  I picked up the phone that night, knowing what would happen but somehow convinced myself that it wouldn’t.  I had been engaged for all of four months now and I knew I shouldn’t make this call.

This was my first time.  Throughout our relationship I had been faithful, going so far as to turn down anonymous sex once or twice.  I don’t remember what came over me, but in a moment of weakness, I dialed her number.  Bailey answered, “Do you want to come over?”  No hello, no how are you, just “Do you want to come over?”  “I’ll be there in 30 minutes.”

Bailey and I had a strange relationship.  I was pretty sure neither one of us really liked the other.  A few years before we had hooked up and had amazing, toe-curling sex.  But that’s about it.  No dinners, no movies, just fucking.  We were both reasonably young and used each other to explore the limits of our sexuality.  As my relationship with my future wife developed, I stopped calling Bailey and she stopped calling me.  I didn’t miss the sex at all, at least not until this night.

I knocked on the door and tested the knob.  The door was unlocked so I walked inside and saw Bailey sitting on the couch in the living room, wearing just a tiny, tight tee shirt and panties.  She walked to me and her hands went to my crotch as she planted a very steamy kiss on my open lips.  “You’re engaged now, so I’m pretty sure you didn’t come over to chat.”  She dropped to her knees and started fumbling with my zipper.  My hearbeat raced; a combination of the excitement of the situation and the beautiful blonde on her knees trying to get my cock out of my pants.  She succeeded, pulling my hard cock out of my jeans and swallowed it whole.  During our previous “relationship”, Bailey grew from your average college girl to a sexually confident woman.  She knew what I liked and she knew how to please me.  After about five minutes of this attention, she stood up and beckoned me to follow her to her room.

Once in the bedroom, I pushed her roughly over the side of the bed and pulled her panties down.  She knew how much I loved the sweet taste of her pussy and how aroused I got when she was freshly shaved.  She didn’t disappoint.  Pulling the flimsy panties down, I buried my face in her, spreading her ass to get to her plump, soft lips.  Though she didn’t need any help getting wet, I loved to suck, lick, and nibble on her beautiful pussy.  The saltiness of her arousal made me even harder, wanting her even more.

I threw my jeans off and pushed her forward on the bed a little.  Guiding my cock towards her, I used one hand to hold her fast against the bed.  Her pussy was so tight that, combined with the strange feelings of cheating, I almost came at once.  Regaining my composure, I started to pound her harder and harder.  Bailey always enjoyed it a little rough and this time was no exception.  I reached forward and started tweeking her clit in time with my thrusts.  She started to groan as I hammered away from behind her, a sure sign she was going to cum.  As her orgasm hit I had to focus all my energy and will on not shooting my load too soon.

As she regained her composure a bit, she reached back and grabbed my cock.  “I know what you really want,” she said, pulling my slick cock from her cunt.  She guided the head to her asshole, pushing her hips back a little and working my cock up and down in her ass.  I had been the one to introduce her to anal sex and, although she was skeptical at first, this soon became one of our favorite adventures.  “I bet she doesn’t let you fuck her here,” she hissed as my head entered her ass.  She got the answer about thirty seconds later when, just as I was starting to fuck her faster, she clenched her ass around my cock.  With no warning, I screamed out that I was cumming and started pumping my cum into her ass.  The orgasm coursed through my body, almost making my knees buckle from pleasure.  As the waves of pleasure subsided, I slumped forward, laying on top of her as my cock softened in her ass.

This would be the last time I saw Bailey.  She calls or emails maybe once a year, generally when she has just ended a relationship or is looking for a reason to end one.  Every so often she sends me a picture taken with her camera phone.  Last night I answered my phone to find a grainy shot of her, leaning over the side of her bed, some guy’s cock buried in her ass, with her looking over her shoulder, smiling.  “Thinking of you” was the only message.

Written by sexualexploration

August 6, 2008 at 10:45 pm

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Tagged with , , ,

Sugasm #143

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This Week’s Picks

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Written by sexualexploration

August 6, 2008 at 9:34 pm

Posted in Uncategorized

Friends of Jefferson

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Reposted from Wanton Maleness:

An important member of the sex-positive community
urgently needs our help.
Jefferson—blogger, educator, and dear friend to so many of us—is at this moment fighting a court battle with his ex-wife, who is seeking full custody of their three children.

Jefferson’s love for his children has been well-documented on his blog One Life, Take Two for years. His ex-wife has stated in court that he is a “great” father who loves his children.

However, among her claims is that his bisexuality makes him an unfit parent.

Jefferson needs our help now. As a writer, his resources are limited. The costs of fighting this case are mounting quickly—and will certainly run into the tens of thousands of dollars.

As of today, there is an urgent and immediate need for at least $20,000 to cover costs associated with attorney fees and those of the law guardian who has been appointed to represent the children.

If he is unable to pay these fees by August 11,
he will be forced to relinquish custody of his children.

This case is of concern to anyone whose sexuality does not fit the standard mold—because it could happen to you. This case is of concern to all writers, because Jefferson’s blog is being used as evidence against him—and that could have repercussions for our First Amendment rights.

Here’s how to help:

1) Make an ANONYMOUS, TAX-DEDUCTIBLE contribution to Jefferson’s legal defense by visiting the Sexual Freedom Defense and Education Fund at:

www.sfldef.org

There you will find out how to donate to Jefferson’s Defense Fund via PayPal or if you prefer, check or money order.

Please note that you MUST mention that your donation be used for the JEFFERSON LEGAL DEFENSE FUND.

2) Feel free to copy this and post it to your blog or any email lists Or link back to this post.

In the coming days, www.onelifetaketwo.com will be relaunched with information about Jefferson’s ongoing case. Be sure to visit his blog for updates. In the meantime, you can contact Jefferson directly at friendsofjefferson@gmail.

Written by sexualexploration

August 6, 2008 at 2:10 am

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Tagged with ,

Pre-MILF III

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As we walked in the door it was very clear that her husband had been perparing for this all evening.  He was sitting on the couch with a drink in his hand.  I introduced myself.  He stood up, shook my hand, and handed me a drink.  Hubby was a good looking guy; tall with blonde hair and a nice tan, well defined muscles and piercing blue eyes.  He looked at me approvingly and nodded to his wife.  She disappeared into the bedroom, the door closing behind her.  Hubby and I sat down on the couch.  “So, she explained what’s going on, I guess.”  Uh-huh”, I grunted; by this time, I was almost completely comfortable with this situation.  I returned to my drink, watching hubby out of the corner of my eye and staring at the TV.  There was considerable silence, but it wasn’t uncomfortable.  “I guess I should explain the ground rules then,” he started.  “First, I don’t mind a little touching, but I am not bi and don’t want anything to happen between the two of us.  Second, she is in charge, so if she says stop, you need to respect her.  Third, nothing is off-limits to start, but if there is any question about something, listen to her.  Finally, I hope you’re ready because this is going to be a long night…”

About this time, Melissa entered the room, topless with a small pair of boy short panties on.  I am sure this was accidental, since we didn’t discuss my preferences, but boy shorts are a huge turnon for me.  She stood in front of us both, posed a little, and then dropped to her knees in front of me.  Undoing my pants, she slid them off and tossed them to the side.  Her head dropped to my cock while her hands started to play with my balls.  She had amazing technique.  After I was fully hard, she started to move up and down on my cock, applying consistant suction.  As her head reached the tip, she started moving her hand up and down my shaft.  At no time was my cock not either being played with or sucked and the feeling was amazing.  As she started to really get into sucking me, hubby came in behind her and moved her onto all fours.  I watched him slide down her panties and spread her cheeks.  He dove in, planting his face in her ass and pussy from behind.  The attention that she was getting caused her to increase the pressure and speed of the blowjob.  Looking back, I don’t know how I lasted as long as I did, but I didn’t cum right away.  Hubby continued to get her wet for a few more minutes, but soon he stood up and took off his pants.  He positioned himself behind her, squatting down a bit to access her pussy.  I could tell when he entered her because she took me all the way into her mouth and kept me there for a few seconds.  This was simply too much.  “Shit,” I yelped, “I’m cumming!”  She didn’t miss a beat, taking what must have been a huge load without missing a beat.

After cleaning my cock, she leaned forward, kissing me on the lips and rubbing her beautiful tits on my chest while she took her husband’s cock deep in her pussy.  I tasted the saltyness of my cum, but, for some reason, it didn’t seem strange or overpowering.  She used my body as a brace, leaning forward and arching her back so her husband could do his thing.  He started to speed up and make a little more noise, I knew he was getting close.  The sound of their bodies slapping together, the squishyness of her pussy and and sound of his balls slapping against her started to get me excited.  He reached up, grabbing her hair, and slamming his cock into her harder and harder.  I slid forward a bit, moving one hand to her tit and the other to her clit as he pounded her.  I made sure not to touch his cock, but it was hard not to feel him thrusting inside her as I toyed with her clit.  As he got close he started getting more and more vocal.  “Do you like sucking cock while I fuck you, you dirty little bitch?”  “Do you want me to cum in your hot little pussy?” and finally, “Jesus, I’m fucking cumming!”  I could feel her starting to cum as he shot his load inside her and I tried desperately to help the process along by flicking her clit and rubbing her lips.  She tensed up, taking his load deep inside her pussy, but didn’t cum.

Melissa’s mouth went to my cock again while he stayed inside her as he got soft.  After the scene I just witnessed, my cock needed very little help getting rock solid again, but she worked the head a little, just to make sure.  She stood up and I could tell she was working to hold his cum inside her.  “How do you feel about getting seconds?” she asked, moving to straddle me, her knees on either side of my legs.  Normally this would have been a turnoff, but this was anything but normal.  Instead of answering, I simply grabbed my cock with one hand and guided her down to me with the other.

My cock slipped into her easily, her wetness combined with hubby’s cum making a sloppy soup of excitement between her legs.  However, my fear that she would be too wet or too loose was soon put to rest as she started to grip my cock with her cunt muscles.  Moving from her knees, she planted her feet on either side of me, giving her a wider range of motion to ride my cock.  She started to glide up and down my cock, leaving me with little to do but watch her tits bounce and enjoy her hot, dripping pussy.  I looked down and was instantly amazed by the sight of her pussy taking my cock and the site of hubby’s cum dripping down my shaft and balls.

As she rode me, I noticed hubby jacking off to the site of my cock in his wife.  After a few minutes, he came in behind her again, this time grabbing her hips so he could aim his hard cock.  “Don’t freak out here, I’m going to get inside her too.”  I figured he would take her ass now, but I soon felt his cock sliding into her pussy from a different angle.  I had never imagined we would both be in her pussy, but he was soon sliding inside.  The feeling was intense, to say the least.  The sensation of his cock rubbing against mine and her tight pussy gripping both of us was too much for me.  I cried out that I was cumming and started dumping my second load of the night into her pussy.  My cock convulsed and jerked as Melissa grinded her clit on me.  Even though I came, my cock stayed mostly hard inside her pussy.  Melissa leaned forward, resting on me, my cock in her pussy, and her husband working like a steam piston inside her cunt.  Between the tightness and the feeling of his cock, I knew I wasn’t going to go soft right way.  I grabbed her ass, pulling her down on my semi-hard cock while he hammered away at her from behind.  Reaching to her cum drenched pussy, I got my finger wet with our cum and slowly started playing with her asshole.

At first, I just circled her rosebud, but soon I was pushing one finger into her little hole.  The angles weren’t perfect, but I could get my index finger into her ass with ease and started working a second finger inside.  By turning my wrist a little, I could feel his cock through her ass, sliding back and forth as his orgasm built.  Figuring she needed to cum too, I started working my fingers back and forth while trying to touch his cock through her ass.  After only a second or two of this, her pussy tightened up and she started cumming, two cocks in her pussy and my two fingers in her ass.  Between my cock in her pussy, his cock in her pussy, her orgasm, and my fingers pushing against his cock, hubby grunted loudly and started shooting his second load into her.  The feeling was amazing; the hot stickiness of his cum filling up her pussy and slathering my cock with his cum.

He pulled out and she lifted herself from my cock, trying very hard not to drip cum from her well used pussy but failing to keep it all in.  Hubby plopped down beside me and Melissa went to work cleaning our cocks with her mouth.

“How do you feel about creampies?” hubby asked as she licked his cock.  “Well, I can’t say that I know exactly what it is…”, I replied.  He explained that some guys get off sucking cum from a freshly fucked pussy.  If someone would have asked me a few hours earlier, I would have been disgusted at the idea of eating my own cum, much less the load of another guy.  But lots had changed in the past hours, so I just shrugged and looked to Melissa for guidance.  She grabbed hubby and moved him to the floor so he was on his back and she was standing over him.  She squatted down slowly, while he stuck his tongue out a little.  I could see the first bit of cum start to drip from her pussy as she sunk down on his face.  “I’ll try to save you some, if you want.”  Though my head was spinning, I figured it was one of their fantasies, so I would try hard to fulfill it for them.  As an answer, I crawled onto the floor and took my spot beside her husband, laying on my back.

I could hear him licking and sucking her pussy from my spot beside them both.  This was highly erotic, knowing that this guy was eating my cum and his cum from his wife’s well fucked cunt.  She lifted herself up and threw her leg over my body, coming to rest squarely on my face.  I gingerly stuck my tongue out, probing her lips and exploring inside her pussy.  “Are you ready?” she asked, just as she started to use her muscles to push out a little more cum.  The salty wetness hit my tongue and I worked quickly to suck and lick it all up.  She continued to push with her cunt and I attacked her pussy like a maniac, grabbing her ass and pulling her tighter onto my mouth.  She was grinding on my face and I was trying desperately to get all the cum out of her pussy, but some of it ended up on my face as she rode my tongue.  The grinding and my tongue pushed her over the edge; I could feel her orgasm build and tasted the saltiness of her cum on my tongue as she expelled the last of our cum into my waiting mouth.

Standing up, she started to walk into the bedroom and glanced back at us; “You boys look tired,” she admonished, “you better not be out of energy…or cum.”

Written by sexualexploration

August 5, 2008 at 11:14 pm

Posted in Uncategorized

Pre-MILF II

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Wow.  To say that I was a taken aback would be the understatement of the century.  For an hour or more, I had been planning a very hot night with a older, beautiful, and single woman.  Now, sitting just a few floors below her hotel room, I find out that she is not single and more than that, her husband is upstairs.

We stare at each other for what seems like a full ten minutes.  “Does that bother you?” she calmly asks, finishing a vodka soda and lighting a cigarette from my pack.  I stammer a response that is not terribly clear.  “We have been married for about 18 years,” she explains, “and sex after children can get pretty boring.”  She goes on to explain that they started going to strip clubs about five years ago, just to do something different.  After becoming a regular at their local club, one of the dancers asked if they were interested in doing a threesome.  More specifically, was the hubby interested in watching the girls get together.  After a brief discussion in the VIP room, the decision was made to try it out.  This would be the first of many threesomes for the stunning blonde at the stool next to me.

She went on:  After hooking up with the dancer a few times, things fizzled out.  But there was something highly erotic about watching Melissa receive pleasure from someone else, her husband explained.  For about a year, this was limited to hooking up with girls from a strip club or from a bar.  Her husband didn’t participate with the additional partner, just with Melissa.  One night they headed to the bar to find a girl and had terrible luck.  Thinking that the night would a bust, they resigned themselves to getting hammered at the bar.  About that time, a group of guys walked in and sat close to the couple at the bar.  After a few minutes, one guy struck up a casual conversation with Melissa and her hubby, just being friendly.  According to her, it seemed like they were old friends despite the obvious age difference.  The guy in question was just out of college, at best.  As the night wore on, it became obvious to Melissa that the guy was attracted to her.  Grabbing her husband, they headed to the dance floor to talk about the possibilities.  Though this took more convincing, her hubby finally agreed to let her take the college guy home.

So now, four years later, I was going to reap the rewards of this brave soul that chatted Melissa up at the bar that night.

Melissa explained that her husband normally participated when she was playing with men.  I should expect him to watch us start messing around, but as things progress, he would become more involved.  She asked how I felt about casual contact with another guy.  Not that he is interested in guys, she said, but that in the course of having a threesome, I should expect some contact.  She further explained that she had her tubes tied, so I didn’t need to wear a condom.  Copies of an up to date STD test were upstairs, if I needed proof of their status.  “We’ll just have to take your word on your health, unless you happen to have test results in your pocket.”

I sat there, taking this all in for a few minutes.  I was clearly interested, since I had not run out the door when she broke the news.  As I let this all soak in, she started slowly rubbing my knee in the darkness of the bar.  Taking a deep breath, she grabbed my hand and moved it under her dress, first to her thigh, then slowly to her completely shaved pussy.  “Even if you are a little timid,” she said, “this will make it all worthwhile.”  I could feel the wetness on my fingers, even without entering her.  As a matter of fact, I was pretty sure she would leave a spot on the booth, judging from the wetness.  She started slowly rubbing my hand on her lips, then let go so I could explore.  I gently ran my finger up and down her soaking slit, stopping occassionaly to play with her clit or spread her lips.  I removed my hand and lifted it to her mouth, where she licked her wetness from my fingers.

If I had any doubts, they all flew out the window.  “Let’s go.”

We closed our tabs and headed to the elevator and then to the 12th floor.  It was all I could do to not have my knees collapse from the stress and nerves.  Turning the corner, I saw the entrance.  1232.  She pulled the keycard from her pocket and opened the door.

“Honey, I have a friend with me.  Are you still awake?”

Written by sexualexploration

July 30, 2008 at 12:13 am

Posted in Uncategorized

Pre-MILF

with 2 comments

Even though the term MILF existed before American Pie, it didn’t gain traction in the English language until after Stifler’s Mom showed up.  This is a recap of one of the greatest nights in history, for me at least, a night that I was exposed to a completely new lifestyle and a few new experiences.

There was a local bar that all my friends from college spent a considerable amount of time in.  The bar was close to school and liked having us college kids there, since we were spending our parents’ money and most of us tipped well.  More than just a bar, it was a restaurant that served pretty good food until about 9pm.  The dinner crowd was eclectic, but after the band showed up and it started getting loud, most of the families scattered, leaving only us college boys.  This was a guys hangout.  The only women that ever came in did it on a dare, by accident, or as part of a bachelorette party.  OK by us, we just wanted to hang out, drink beer, and tell lies.

In late August of my senior year in college, I headed to the bar, just as I did almost every other weekend night.  I got there about 10pm and noticed that the bar was a little deserted.  There were a few groups of my friends so I grabbed a beer and started making the rounds.  A while later, I headed back to the bar to grab another drink.  As I was walking away, someone tapped my arm and asked for a light.  I turned to see an absolutely beautiful, slightly older, woman sitting at the corner of the bar.  She was turned around, facing the crowds, seeming to enjoy the scene.  Reaching for a light, I quickly lit her cigarette and started away.  Returning to my table with the guys, I noticed that she was scanning the room, but seemed to have fixed her gaze on our table.

Returning to the bar, I went to order another drink, but the mystery woman quickly stopped me.  “A Budweiser…” she asked, sliding a cold, fresh bottle my way.  “I’m Melissa” she said, extending her tanned arm.  I introduced myself and asked if I could sit with her.  We chatted for a while, then I mentioned that she seemed a little out of place in this bar.  Visiting from out of town, she explained, before pointing to the brand new hotel across the street from the bar, “I’m here for a few days on vacation.”  Making small talk is not a strong suit, so I struggled to keep the conversation going.  No ring on her finger, but she mentioned that she had two kids who were staying with their grandparents while she was in town.  Melissa, it turned out, was a sexy forty-four years old, but had a body to rival the girls at my college.  Tanned and trim, with short blonde hair and bright blue eyes, she could easily pass for 30.

Not wanting to appear too desperate, I wrapped up the conversation and headed back to my table of friends.  I kept my eyes on her as she finished her drink, ordered another, and quickly finished that one.  One more cigarette and she headed to the bathroom, and I thought, out the side door.  Giving my attention to the table again, I was surprised when she came up behind me and leaned over.  “I am walking over to my hotel room right now and would like it if you came along.”  Never in my short life had a woman been so forward with me.  I stammered for a second before my buddy Ray spoke up for me, “I’ll close your tab.”  What else could I do?  I chugged my beer, grabbed my smokes, and walked out the door with Melissa holding my arm.

Instead of heading right for the room, we detoured to the bar, a swanky sort of place with jazz, cigar smoke, and professionals, a far cry from the grungy pub we just left.  We sat in one of the small booths towards the back and ordered a few drinks, switching to scotch to help calm my nerves.

Melissa was lightly touching my leg, not aggressively, but just enough to let me know she was there.  We chatted a little more and soon the conversation turned to her family.  Not knowing what else to say, I asked about her kids.  She told me a little about them and turned the conversation to her husband.  “Ex?” I asked, hoping for clarification.  “No.”  Um…  “Is he with the kids,” I asked, “I thought they were with your parents?”  No, she replied, he’s upstairs…

To be continued

Written by sexualexploration

July 25, 2008 at 12:18 am

Posted in Uncategorized

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Upskirt Tease

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So I got to work early today, hoping to get a headstart on the week.  I am normally the first person in the office, even when I get in at my usual time, so I was a little surprised to see Megan in so early.  Megan and used to flirt occassionally, especially at our all too frequent happy hours.  Since I’m married and so is Megan, I just don’t see the harm in a little healthy tension.

This morning came as a bit of a shock though.  Megan is about 10 years older than I am, with an amazing body that the average 25 year-old would kill for.  She was sitting at her cube in a reasonably tight skirt, with her long, tan leg tucked under her butt.  Five minutes after I walked in, she called for me to come over to her desk.

I turned the corner just in time to see her adjusting herself in the chair, giving me a fleeting upskirt glimse.  Clearly not intentional, but exciting nonetheless.  Being a bit of a nerd and the department’s go-to guy for small computer problems, she asked me to give her a hand with a simple problem.  Kneeling down by her computer, I quickly figured out the problem but was distracted by her moving around in her chair.  Though the first glimpse was obviously an accident, I must have “glanced” too long, because she seemed to notice how distracted I was.  It seemed like every five seconds she moved one leg or the other, tucked her skirt in, or generally fidgeted about.  Each time her movement caught my eye and each time she seemed to linger a bit longer with her legs open.  To my dismay, she was wearing normal panties, so no full on view, but it was still highly erotic and distracting.

On her way out of the office today she stuck her head in my cube to “Apologize for being such a distraction.”  The sparkle in her eye and the slight grin seemed to say it wasn’t an accident.

Written by sexualexploration

July 21, 2008 at 11:29 pm

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