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Archive for July 2008

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?”

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July 30, 2008 at 12:13 am

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Pre-MILF

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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

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July 25, 2008 at 12:18 am

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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.

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July 21, 2008 at 11:29 pm

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First Time Strap-On Play

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As I sit down to write this, my hands still shake a little.  About 5 years ago I started hanging out with Courtney.

Courtney is about five years younger than me and an absolute fucking machine.  Over the three years we hooked up, there was nothing I could cook up in my sick little mind that she wasn’t willing to at least try.  Be it a threesome with her suitemate from college or a foursome with my two best friends, this girl was an absolute freak.

Courtney called me one afternoon and asked me to come over to her dorm room.  Since it was a beautiful weekend, her roomies had decided to head to the beach but she didn’t feel like going.  For some reason we had not hooked up in almost a month.  Nothing was wrong, but we were both busy and didn’t seem to be able to connect with each other.  During the previous week, Courtney had left me a few suggestive voice messages, promising me an unforgetable weekend.

She called me on Friday afternoon to confirm that the girls were at the beach and the entire apartment was hers for the weekend.  She mentioned that she had found something that I might be interested in, but refused to tell me any more.  Since I had never gotten close to the limits of her sexuality, I had no idea what she had in mind.

After work on Friday, I headed to by buddy’s bar and gave her a call.  Normally not one to miss the chance to go drinking, I was amazed when she said that she was staying in Friday.  Courtney was only 20 at this time, so she almost never gave up the chance to go out, especially when she knew no one would card her.  I explained that I would like to have a few drinks to relax from the weekend and she replied “You might want to have a few extras, just to loosen up.  You’re never going to guess what I have in store for you…”

When the phone went dead, I was left with a beer in my hand and my jaw on the floor.  I couldn’t even imagine what she had in store.  I hung around for about another hour, drinking steadily and running over the possibilities in my mind.

I got to her place about 8:30.  She answered the door in a baggy pair of sweats, her hair up, and no makeup.  Not that she was unattractive, but she normally liked to get a little dressed up if we were staying in.  I was the first guy that bought her lingerie and she absolutely loved wearing just about anything that showed off her body.

She opened a bottle of wine and we sat down on the couch.  After a few minutes of normal conversation, she asked me if I trusted her.  She went on to explain that she had indulged many of my fantasies and, although she enjoyed them all, she wanted me help her live out hers.  Why not, I thought to myself, what could she possibly want to do that I haven’t already jerked off to…

She led me to her suitemates room and helped my out of my pants.  Her roommates had a little grudge going: each of them liked to fuck on the other roomie’s bed, in the name of harmless fun.  So we were in the other room, the lights turned down a little, but her figure still very clear as she walked around the bed.  I was laying on my back, pants off, feet on the floor, and my ever hardening cock beginning to rise.

“Close your eyes.”  I did and my head started spinning with the possibilities.  I could feel her get closer to me, kneeling down between my legs and taking my cock in her mouth.  She spent a few minutes getting me hard before pulling my cock out of her mouth with a loud pop.  “Let me know if this makes you uncomfortable.”  With that, she took the whole length of my cock in her mouth as she started to play with my asshole.  First it was just the one finger, playing outside my hole.  As she worked harder on my cock, she started getting a little more aggressive with my ass.  She grabbed a little lube from the table and coated her finger.  I don’t know how to describe the feeling of her finger entering my tight ass; a combination of pleasure and uncertainty.  On her knees, she worked the shaft with her mouth while she played with my balls and toyed with my asshole using her free hand.

“What do you think of my finger?” she asked, taking a break from blowing me.  “Uh, well, it’s different, but not painful.  When your whole finger is in there, I feel like I’m going to cum really quickly.”  “Should I stop, or keep going?”  Since she had not stopped playing with my cock as she talked, I was getting really close to cumming.  “Keep going”, I implored her.

With that, she stood up and I noticed that she was completely naked, standing between my legs with my hard and wet cock in her hand.  She bent over at the waist and fumbled with something on the floor.  As she stood up, I noticed something was different, but with the low light I couldn’t tell exactly what it was.  She turned sideways and it all became clear.

“I found this in Jenny’s room last weekend” she said as she squirted a bit of lube on the strap on cock now firmly fitted to her waist.  My eyes bulged, but I didn’t move.  It was about my size, just under 7 inches long, but a bit thinner than my own cock.  My eyes were glued to the fake cock; even as she told me the story, I was focused only on her toy.  “I noticed a strange noise coming from this room last weekend.  I knew Jenny was hooking up, but something about the noise was unusual”, she explained.  It seems that Jenny is even kinkier than I imagined.  This is the same girl who agreed to a threesome with Courtney and me.  But I had no way to know how genuinely dirty she was.

The next morning, after the guy left, she asked Jenny about the strange noises.  Blushing, Jenny explained the whole thing.  The guy she was hooking up with was into strap-on play.  Jenny, like Courtney, was open to most suggestions and, though a little put off by the request, agreed to play along.  The guy brought over his “favorite” toy, the strap-on setup that Courtney was now wearing.

Without any further ado, Courtney moved between my legs and told me to move my legs onto her shoulders.  “Just let me know if I need to slow down” she instructed as she lubed up her fake cock.  With my ass in the air and my legs over her shoulders, she started to rub the head of the toy on my ass.  Already lubed up from her finger, she didn’t waste too much time on this, choosing instead to work just the head of the cock into my rear hole.  Now, I have convinced more than one girl to let me try anal with them and try hard not to make the first time hurt too much.  As I felt the head press against my ass, I thought back to my instructions to my anal-virgin partners.  “Take a deep breath and as you feel the head push against your ass, relax.  As the head goes in, keep breathing and push a little.  This relaxes the muscles and will keep anything from hurting too much.”  Always seemed to work for me, but it’s a whole different story when it’s your ass.

So I started breathing and as the head popped in, I pushed a little, just to ease the pain and help my ass get accustomed to the visitor.  Before I knew it, Courtney was all the way in my ass.  To start, the pain was pretty intense, but as she worked up a little speed, it subsided and the fullness in my ass became more and more pleasurable.  Just as I was starting to get used to the feeling of her in my ass, Courtney bottomed out in my ass, thrusting deeply as she played with my cock.  The sight of her beautiful tits bouncing as she stroked my ass and played with my cock was just too much.  Before I could warn her, I erupted, shooting long, thick strings of cum all over our stomachs.

Pissed at me for cumming too quickly, she jerked the cock out of my ass and grabbed me by my hair.  “You goddamned pussy” she screamed, “you can’t even take a solid assfucking.”  Pulling me off the bed and onto my knees, she grabbed my chin and ordered me to lick my cum off her.  Overwhelmed by the sudden change in tone, I didn’t know what to do, other than stick out my tongue as she forced my mouth to her stomach.

The sudden shift in her mood foretold a change in our relationship, but I was too overwhelmed to notice at the time.

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July 21, 2008 at 10:31 pm

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Sexual Exploration

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I think we have all spent time daydreaming about our previous experiences and our desire for new adventure.  I hope you enjoy this blog; it’s simply a chronicle of my experiences and my current sexual situation.  Most of the posts will take the form of stories, so bear with me as I get long winded.

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July 19, 2008 at 8:44 pm

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