A cuckold sendoff for my lover
written by:
LoveAshli

Let me say how wonderful it was to read a story from an old friend and author I personally always admired, JenniferO. It inspired me to get back to writing at least one more update, realizing it has been a few years since my last story, and over 10 years since I first submitted to ES. The fans have always been wonderful, but in the past few years I began a personal exploration that took my needs and desires beyond that of the written word and into my everyday life.

My early stories were written based on actual experiences. Truly I have been blessed in my life. Not only do I have two wonderful children, but genetics blessed me with a body that adapted well to pregnancy. It runs in my family. But also does the hormonal levels in our 30s. It would be some time before my older sister, and even my mother, would tell me of the crazy needs my mind and body would want to experience. And as they told me about them, I instinctively knew it would be my destiny as well.

Over the past two plus years, my transformation from a "MILF in training" to a vixen was complete. In years past I would try to convince my husband to experiment and try new things, but my needs would be too great, and his long work hours would make it impossible to satisfy. But don't get me wrong. I adore him as a friend, spouse and father of my children. But to satisfy my urges, I would need to open up to new experiences and perhaps people to make those fantasies come true.

It would begin harmlessly, as do many stories, with an old friend from high school, catching up online and at a reunion. He was always the sweetest of guys in my teenage years, always treated me kindly, but it wouldn't be until the recent present that he would admit a long standing crush he had for me.

Life had been good and not so good for him. He became very successful in his career, and on paper looked like the perfect man. He married a sorority president and had very intelligent boys, but health issues would transform his marriage into a true "brother sister" relationship....the silent divorce that so many people experience.

He was an up and coming executive in a rather large national company, and his career had just recently brought him back to the area when we caught up at the reunion. I won't bore you with the details, but both having admitted our intimacy needs, started a relationship that would be mutually beneficial.

Most of our time together would be in the afternoons. I work, not for the money but for the opportunity to be around adults, not dress like a soccer mom and actually feel some sort of self-fulfillment. We would take long lunch breaks together, finding time to build our friendship but also satisfy our lustful needs. We became regulars at a fun little motel in our area called the "Hollywood" when one step inside the room assured you it was only built for sex. Mirrors all over, dark lit rooms and xxx-rated movies on the television. It was cheezy but fun. We'd spend most of the three hours tearing at each other's bodies like animals in heat and give ourselves just enough time to clean up and be presentable for the real world.

It was probably eight or nine months before I would realize that both he and I shared a cuckold fantasy. Actually the idea never crossed my mind, but on a rare evening I could get free, he asked if I could join him for a dinner meeting with a very important account he was trying to win. The deal would be huge for his career and the company. I was the good girl and showed up in a professional but sexy outfit. It was a short skirt suit and I was brazen enough to go without a blouse under the suit. A mere two buttons held my bra and breasts from his sight.

Over dinner, I did my part and flirted with the client. I had met him once before when I caught up with Jackson at a trade show in Manhattan and thought the guy was cute, so was willing to go along with it. Over dinner and drinks, Jackson would remain sober to drive, I became buzzed but the client got pretty wasted. Excusing myself for the restroom, Jackson met me on the way back to say Peter couldn't stop talking about me and would do anything to have me.

Even before he asked, being the good girlfriend, offered to do my job as his "assistant" and help him win the deal. Both Jackson and Peter were staying overnight at the same hotel, and I had the alibi for the evening thanks to a close girlfriend. I waited by the ladies room while Jackson worked his magic with the client, likely agreeing to a deal that I would help seal. After we finished dessert, Jackson got the car. He drove. I sat in the back seat with Peter. Before long, I would feel his hand reaching up my skirt. It wasn't another five minutes or so that Jackson would look back, having adjusted his rear view mirror to see me seated but leaning over his multi-million dollar client, his drunken cock swallowed in my mouth.

When we got back to the hotel, Jackson walked us both up to Peter's room. Before leaving he whispered to me "Are you sure Ash? Say the word and I will stop it."

"Shhhh big boy," I assured him. "He can have me for an hour but you will have me for the entire night." Luckily a smart girl always plans for such possibilities, and some extra condoms in my purse would go to good use. Between the drinks and the blowjob I gave him on the car ride, it wouldn't take Peter very long to be on top of me missionary and cumming inside me. It couldn't have been more than 30 minutes that I would collect my things and leave the now passed out Fortune 500 executive in his room and make my way back to Jackson's just a floor below.

When I arrived, to my surprise, he wanted to hear details about what happened. As I described little portions, him seated on the bed watching me stand in front of him getting naked, Jackson became heated in passion and started ravaging me on the spot. He found more and more desire hearing me describe how I took this very powerful man and had him wrapped around my finger to do as I wished.

So not only would he win the big account, and I would receive a very generous gift (my husband still thinks the diamond necklace is just costume jewelry...he has no idea). But I would realize that I enjoyed Jackson watching me with other men as much as he took pleasure in watching "his woman" be wanted and seduced by other men.

Over the next several months, we'd begin to explore this side but never too far. I went with him to a swingers club in Manhattan just for the experience. We swapped with another couple, but I have to admit I prefer being the center of attention and the only woman in the room. Jackson too was not so much into other women. Either because he was worried that I might take offense or perhaps because there would be no woman that could compare to me. I was willing to accept the latter as the reason :)

But it wouldn't be until this September when we would push it much further. His recent successes gave him an opportunity to assume a executive vice president role, but one that would require his relocation to the west coast. For some time, he appeared unwilling to accept the new position, perhaps for fear of losing our relationship. But after some coaxing, even from me, he made the right decision for him and his family, and soon would be moving west.

It would be a Saturday night, Jackson would get together with several of his local guy friends for a sendoff. He and I spoke about the sendoff, and he shared his one fantasy to see me as the center of a gang bang, something he knew was a fantasy I had shared with him, but never had the guts to go through with. He told me that all of the guys going were married, and even one was another guy I knew from high school. So Jackson and I started talking and making some secret plans for him and his buddies, to make his send off one that he and I could remember for a lifetime.

That Saturday evening, the five men would find themselves at a sports bar near a local college and inside a Marriott hotel. For five husbands and many of them fathers, this was a wonderful getaway itself; an evening drinking, watching baseball and just able to let loose and say what they wanted. Things would take a turn for the memorable just as I walked in the door after 9pm.

My alibi girlfriend was set, every woman needs to have a friend like that, and I took the afternoon to get my hair done as well as a manicure and pedicure. I wanted it to be memorable so I got very brazen with my approach for the evening. Rather than select a dress, I wore simply a black lace demi bra, thong and garter belt, with black stockings and boots, covered simply by my ¾ length coat. I finished off the look with large, fashionable sunglasses. In addition to the usual, my purse would contain a large pack of condoms, my little pocket rocket, lube and a hair and tooth brush.

Entering the hotel bar, I felt dozens of eyes on me, as would be the case at any hotel bar. But as I walked over to the guys in their large semi-circular booth, I became self-conscious. I was getting so turned on by the thought of what awaited me that I was feeling my pussy dripping in anticipation. I almost thought about first going to the ladies room to take the edge off with a quick masturbation, but instead used the energy to walk over to the table.

"Hello boys.....hi Jackson," I tried to say in a sultry tone. I felt like I was acting out a ridiculous porn scene, but knowing what was ahead made it feel very real to me. Jackson introduced me to everyone, and I had a quick hello and smile for all, especially Kevin, who I also knew from high school. I wasn't sure what they knew coming into this but I suggested they let a girl in the middle so they got out of the booth as good gentlemen and let me get situated inside. Of course doing so with a coat and not much else on wasn't easy.

We spend the next half hour or so talking, ordering some drinks and shots, as I became friendly with the group. Jackson has his hand on my thigh most of the time, seemingly to try and unwrap my coat to see exactly what I had, or didn't have on. I would causally flirt with the other guys and harmlessly touch their hand or knee, depending how close they sat to me.

It was during a commercial for the game, when the conversation seemed to die off among the group, making it the perfect opportunity for me to make my move. "So boys, why don't we move this party upstairs? I'm sure you can get a room, no?"

I think the words froze them in their seats. It appears my boyfriend wanted it to be a true surprise for them as well. For the past several minutes I could tell the guys were making eye contact with each other, trying to determine what I was wearing under my coat. So I pushed the envelope a little further. Since we were tucked away in a corner of the bar, I casually opened my coat, just enough to let the boys see my lingerie and nothing else.

As they struggled for the words, Jackson offered to go get a room for the evening. And like a perfect gentleman, he got us probably the largest suite in the hotel. He came back and handed me the key card. I told the boys to wait a little and then take their time coming upstairs.

I got up to the room, dimmed the lights, found a satellite radio station with just the perfect music for the night ahead. There I would wait, in my lingerie, on all fours on the master bed. Having sprayed myself and the room with perfume, I left my purse and supplies on the nightstand. No sooner was I in position then I heard my man use the other key card for him and his friends to join me in the suite.

All finding their way into the bedroom, I wait there, on hands and knees on top of the bed. "Well funny to run into all of you again," I uttered as each of them appeared unsure what to do next. Truly this was something none of them, myself included, had ever experienced. But knowing Jackson's love for me, I felt safe and knew he would be watching over me. I laid out some simple ground rules for the evening. Condoms were a must for everyone and no anal (although Jackson had special privileges).No overtly rough play, no photos to be taken and I gave them a safety word in case I felt uncomfortable at any point.

"Now boys....strip." I ordered. Each was a little timid at first but slowly they began disrobing and I rewarded the first one done to come closer to the bed. Still on all fours, I reached forward, sliding my hands under his balls as my fuck-me red lipstick cladded mouth and tongue opened up to welcome him inside. It began with me trying to pull him closer, but being on all fours made it difficult to do both. After a moment, Kevin would get the hint and place his hands on my head to bring me closer to his shaft, letting me swallow most of his cock into my waiting mouth.

The other men began circling me, all standing around the bed, each starting to reach out, touch my body, caress my stockings, grab my breasts. The feeling was wonderful, and I couldn't help but notice Jackson, seated in a chair across from the bed, watching in pure delight. He sat there, naked, with his wonderful cock in his hands, stroking it, as he watched his woman being explored by so many men. As I went around stroking and sucking each of them, I took out the condoms, placing each one against my mouth and letting my teeth and lips unroll it as I would suck their cocks.

"Come here baby," as I gestured with my pointer finger, curling it towards me. As I moved my lips to the next cock, Jackson knew I wanted him inside me. So with cocks in both hands, another in my mouth, and others just touching me all over, I felt his bare shaft enter my waiting pussy, which was already on fire at the sensations it was experiencing. As soon as he entered me, I let out a loud moan and started to squirt on the bed. It would be the first of many showers my body would emit that evening.

Once my pussy was christened by my lover, the other men each took turns pumping my pussy doggie style. It felt surreal the entire evening, as many times I could barely see any sights of the hotel room - just the sight of naked bodies and men looking to have their way we me and their cocks wanting to get inside me any chance they could.

Over the next several hours, I would try so many positions as my boy toys would flip me around like a rag doll. What I knew what that no more than a few seconds would pass before a cock would be in my pussy and my mouth, and my body would be groped, pinched and caressed. At some point, my bra and panties found their ways to the floor, my garters and stockings would be destroyed from all the play.

Pretty soon I became more brazen being caught up in the moment. When one of the men said he was about to cum while fucking me, I quickly turned around, popping his hard shaft from my soaked pussy. I quickly yanked off the condom and started to put his cock between my tits when he shot his load across my chest. It felt wonderful, and the look of delight in Jackson's face watching it only made me want to continue to do it. So as each came, they would let their cum cover my breasts, my ass, even my face.

We had probably been fucking for at least two hours when one of the guys suggested ordering up some drinks and food, cause we know you burn a lot of calories and sweat a lot when surrounded by so many men. Jackson went and got the phone to call room service, and there was a knock at the door within maybe 15 minutes.

As he walked into the living room of the suite for the door, I yelled out, "Have the waiter wheel it in here!" Now those of you that remember my old stories may recall how I flirted, but never dared do anything with a room service call so many years ago. But this time, my brazen self wanted the sensation of my lover to stand there proudly as a young waiter watch his lover be satiated by a room full of men.

The waiter, a young college age boy, did all he could to remain professional, and even politely responded with some excuse when Jackson asked if he wanted to let me have a taste of him. But the thrill of being seen as a total slut pushed me over the top as my moaning and panting only got deeper.

But the most memorable moment would be when I was riding cowgirl on one of his friends while sucking another. "Jackson, sweetie, I think your baby needs it," I said. Now so far the closest to dp I had gotten was a man in my ass and a dildo in my pussy. But I wanted to experience how it felt to have my entire body filled with hard cocks.

As a good boy, he took the lube to his bare shaft, and with minimal hesitation, positioned his naked body over his friend. It amazed me to see how easy these guys were willing to let any homo-erotic phobias rest aside for the heat of the moment. Slowly, he started to position his cock along the tip of my ass, initially by holding it and rubbing it up and down along my opening. Once his started to enter me, my body responded by squirting in amounts I never experienced before. The evening would become a haze, as we would continue to fuck for hours until everyone crashed on the beds.

The euphoric haze I was in continued throughout the night. I came more times that one evening than ever before. I would recall waking up a few times overnight, as one or more of the men would suddenly be awake and wanting to be inside me again. I didn't hesitate. Each time they knew to condom up and they were free to do as they wanted with my body.

That morning, most of the men left early, leaving Jackson and I time for one more fuck session together before jumping in the shower. For those married men, I knew I had given them an experience they would take to their graves....a smile their wives would never be able to explain. I had no clothes with me, and didn't feel like getting them from my car, so blazingly left the hotel that morning in my coat and heels only, before heading back to my girlfriend's house to change, tell her all the juicy details and spend a relaxing day together.

It's been a few months since Jackson moved and we still speak from time to time, but long distance relationships can be quite challenging. I spend less time on sites like ES and more on ones like SLS, looking for the next man who can satisfy those needs. A man who places me on a pedestal but still respects my boundaries. A man of intelligence and power. One who doesn't need to try and wow me with details about his size or how many hours he lasts, but one with the intellect and know-how that attract women like me.

Maybe that next person is you?

Loveashli