Dee Dee’s Tale

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Eyl 2, 2023 // By:analsex // No Comment

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DeeDee’s Tale

or, How We Found Things In Chicago.

This story is inspired by and dedicated to a wonderful woman by the name of DeeDee. She lives in Chicago. That much is reality.


It was cold and grey as we stepped off the plane at O’Hare. The wind blew which is a cliché for Chicago I know, but blow it did. After the air conditioned pampering of first class, the cold air was a shock to the system, but it woke me up enough to deal with the last part of our journey. I had been invited to lecture at a literary conference being held at the humanities division of the University of Chicago on ‘The merits of Pornography in Literature’. This was a leg of a lucrative tour, and I was allowed to bring my wife.

We checked in at our hotel sometime later. I forget which one. It’s unimportant and anyway, after you’ve stayed in as many as I have, the one is very like another. They sort of merge into a kaleidoscope of neutral colours and minibars! My wife just wanted to change and shower and the porter was hardly out of the room before she started to undress.

We had only been married for a year or so, although we had known each other for some years prior to that. Her name was Michelle; she was 26 years old with a body that hadn’t changed since she was about 18. Her long dark hair contrasted beautifully with her pale skin. Her pert breasts were topped with responsive nipples that stood proud when aroused and her stomach, while toned, had that feminine curve that led the eye to her shaven pussy. Her slender legs left a small gap at the top framing her lips in a hairless triangle and when she turned round, two small globes just screamed to be held. She wasn’t tall, but her piercing blue eyes and that mane of dark hair turned heads when she entered a room.

I frequently asked myself which of the Gods above had decided that I should be so lucky as to have this woman. We had met through my work as a commentator on things pornographic. It transpired that she had never found a man that was prepared to let her express her sexuality for fear of losing her. To me, it was that very sexuality which I found attractive, and we naturally fitted together. I found it hard to think of many sexual acts we had not either partaken of as a couple or watched each other perform. We had no secrets and shared everything….and everyone!

I watched as she slipped off the last of her clothes and padded around while the Jacuzzi in the bathroom filled.

“Are you coming in?” she asked.

“I have to make sure I’ve got these notes straight first,” I said

“Work, work, work,” she chastised me.

“I want a big party when you’ve given this lecture.”

“I promise,” I replied and as we hugged, I felt her warmth and nearness begin to arouse me.

“Get in that bath before I change my mind,” I whispered in her ear, and playfully slapped her backside.

“Ohhh, more please!” came the playful reply as she skipped out of reach pushing her ass out as she did.

I had every intention of joining her after I was satisfied with my notes, but the next thing I knew it was 3.30am as I awoke, still dressed and as I came to my senses, I realized that I must have crashed out. Michelle was sound asleep next to me, naked as was her custom. She wore lots of different lingerie to play in, but always slept naked. I watched her in the half light of the room. Her hair splayed out over her pillow, the rise and fall of her breasts, her smooth tummy, her pussy that was visible between her slightly open legs and those firm thighs. Even in my drowsy state she gave me a hard on.

I stripped off and stretched out beside her. She turned over slightly and pushed her ass back into me and when she felt the sticky end of my cock rub against her cheek, she moaned softly and put her hand between her thighs and guided me into her. She was warm and ready. I caressed her silky body and we made love slowly and tenderly, both of us half asleep, until I came with my cock deep inside her. This kind of gentle intimacy was a special treat for us as our very open sex life normally led to much more erotic and involved sex games.

When we awoke, we showered and dressed and went down for breakfast. My day was planned for me, a tour of the Facility, lunch with several dignitaries and my lecture in the afternoon. Michelle told me she planned to check out Chicago’s opportunities for retail therapy.

“Do you fancy a party later?” she asked

“Sure,” I nodded, “I’ll provide the female company, you find us a couple of guys. That shouldn’t be too difficult!”

“Can’t wait,” said Michelle with a very mischievous look on her face, “Now I know what to shop for!”

I left her to enjoy her day, confident in the fact that on my return, all the necessary arrangements would have been made for our evening’s entertainment. My challenge was to find another woman who would want to join in. I hoped my day at the university would provide me with the right opportunity.

My car arrived and I was driven Mardin Escort to the campus where I was met by the usual tribe of academics and University types who would accompany me for the tour. Sadly, after having seen more campuses, and having met more Deans and Professors than I needed to, I had switched into ‘automatic’ and let the whole thing wash over me until lunch time. A buffet had been laid on with drinks which at least gave me a chance to circulate and escape from the more persistent types who bored me rigid. I had just escaped from a particularly crusty academic type and was making my choice from the buffet when I heard:

“Beats my usual student fare!”

I looked up to see a gorgeous young lady piling her plate with the choicest items from the buffet.

“Hungry?” I teased her.

“When did you last live on a student budget?” she fired back.

“I can remember…vaguely.” We laughed and introduced ourselves.

“I’m Nick Gerrard. I’m here to give the lecture this afternoon.”

“Everybody calls me DeeDee. I’ve been sent to cover your lecture for my literature group.”

DeeDee was one of those girls who it is very difficult to hold a conversation with as your eyes are attracted to her breasts as if by magnetism. I understood immediately when she explained why they called her DeeDee after her bra cup size during her cheerleading days. The thought of her breasts bouncing between two pompoms was a diversion in itself. She obviously had grown used to the effect they had on people because she was so unselfconscious. The rest of the package was as exciting as her tits. She had that beautiful creamy dark skin that was the product of a mixed race marriage. Her fashionably short skirt showed off a wonderful ass sitting on legs to die for. Shoulder length dark hair framed her face and her smile lit up the room. You just had to know more about her.

We shared easy small talk while we ate, getting to know about each other. From her answers to some carefully chosen questions and my own experience, I was sure I had found my contribution to tonight’s party.

“My wife and I always hold a party after these things,” I told her.

“I think you’ll enjoy yourself if you come along.”

“I’d love to,” she replied, “what do I wear?”

I wanted to tell her ‘as little as possible’ but didn’t want to frighten her off.

“Think sexy,” I told her. “Think I want to give every man in the room a hard on.”

“Sounds like my sort of party,” she quipped, laughing.

I gave her my contact details and left hoping the afternoon would pass quickly so that the time would soon come when I would be able to explore her sensuous, firm body at my leisure.

As I was being introduced on the stage of the lecture theatre, I took my customary glance around my audience, and was delighted to see DeeDee right there in the front row. She smiled as our eyes met. I noticed that she was dressed as I remembered, but had removed her pantyhose. I assumed she felt warm at some stage and that was that. And then she did it. She opened her legs showing me that not only had she lost her pantyhose, her panties had gone too, if indeed they had ever been there! I was staring at a perfectly smooth pussy, lips slightly puffy where she was obviously excited. She knew the effect she was having and was loving it. I wondered if any of the others on the stage had noticed and if she would care if they did? It didn’t do a lot for my concentration, but I managed.

After the talk, DeeDee came up to me and played coy.

“I hope you couldn’t see anything,” she said with mock shyness

“I could almost see your cervix,” I joked.

“You can try and find that later,” she said over her shoulder as she left.

I returned to the hotel with high hopes of the evening.

“Hello,” I called as I got back to my room.

“Hello,” came back Michelle.

“How was your day?” I asked her

“Great,” she replied, “I found some great shops and met some very interesting people. I’ve invited two guys for tonight. I know you’ll get on well. How about you?”

I described DeeDee to her the best I could.

“Sounds very nice, she’d better be bi.”

I must admit I hadn’t thought of that, but just had the idea that DeeDee was up for most things.

“Of course she is,” I said with forced confidence, “and if she wasn’t, she will be when she sees you. Now where’s that Jacuzzi?”

The rest of the early evening was split between getting ready and relaxing. I wore a pair of casual trousers and an open neck shirt and Michelle wore a short black cocktail dress. She wouldn’t let me see what she had underneath as she wanted to see our faces later, but the blackness of her hair falling on her pale white skin and the black dress and stockings and high heels made her delectable. I came up behind her and gave her a soft kiss on her neck and breathed in her perfume. Chanel No5. It was almost a part of her I had smelt it so often, but it never failed to arouse Mardin Escort Bayan me.

The first to arrive were the two guys Michelle had invited earlier. Harry was tall, wavy blond hair and conventionally handsome. Bill was shorter, stockier and powerfully built. He was also black. It transpired they ran a small IT company in town, and had been at the restaurant where Michelle had lunched. They were waiting for a potential client who had failed to show, and when Michelle told them she too was alone for lunch, they got together. From their relaxed and confident manner, I was sure she had invited the right people. Minutes later, DeeDee made her entrance.

Too say her outfit had been sprayed on makes it sound too loose. The white PVC dress was zipped from top to bottom, but as the distance between the top of her dress which just held her breasts in to the bottom, which barely covered her ass could have been measured in inches, the zip was winning the fight. Just. Her stockings had to be hold-ups or else we would have seen the outline of her garter belt. Her high heel pumps gave her legs great definition and she would have stopped the conversation anywhere.

“Wow!” was about all I could get out to start with,” come in and meet the others.” Introductions were made and I could tell immediately that we would all gel. DeeDee sat down and in spite of her brave effort to keep her knees together, it was impossible not to reveal an expanse of stocking top and a wonderful flash of white panty. She was sat opposite the two guys and I knew they could see the same. I could feel the atmosphere changing from that start of party awkwardness to a more relaxed moment when more was possible.

We drank wine and ate from a finger buffet full of sensual foods. We chatted and got to know each other just a little. Inevitably, the conversation came round to my work as a commentator on matters pornographic as it always does. People think I must live in a permanent blue movie set, but in reality it has its good and bad moments just like any other job. I will refrain from saying it has its ups and downs, but that’s about it. What I had got from my constant exposure to pornography in all its forms was a very relaxed attitude towards sex in all its permutations. There was little I hadn’t or wouldn’t try.

“Can anyone imagine what this little madam did to me this afternoon?” I asked at a suitable moment, “and she was twenty feet away from me!” I went on to explain what happened and we all laughed.

“I think we need an action replay,” said Harry.

We all agreed on that, and Michelle slid in between Harry and Bill as I sat on the floor, all of us looking expectantly at DeeDee.

“I didn’t know I was the stripper for tonight” she said as she stood up, “but as I’m here!”

The first thing she took off was her skimpy dress. She stood in front of us in a white bra, white thong and stockings which showed off her beautiful coffee and cream skin to wonderful effect. As the other guys eyed her up and down, I was very aware of Michelle taking in every detail. She had dropped her hands either side of her and was starting to rub up and down Harry and Bill’s legs.

End of part 1

Part 2

DeeDee continued. She came and stood in front of me and then dropped to her knees. Leaning forwards, she whispered me to undo her bra. As I unhooked it, she let her breasts fall free. There was an involuntary groan from the others as they took in the sight of her magnificent chest. Her dark nipples were proudly erect and her areolas were the size of saucers.

“Feel them,” she told me and I gladly obeyed. When I had played with her for a while and sampled those nipples in my mouth, I passed her on to the other three. Harry and Bill had a great time while Michelle stood up and kissed her, their tongues dancing as they met. She gently pushed the guys’ hands away and the two girls stood there in front of us. Michelle kneeled down and pulled DeeDee’s thong down with her teeth until it was around her knees. DeeDee shook them down to the floor and kicked them off leaving her in just hold ups. Michelle got her to turn round and played with her ass while we looked on. She buried her face between those sweet cheeks and licked around her anus making her squirm and breathe heavily.

I couldn’t sit there anymore and went over to the girls and pulled DeeDee up and got her to come and sit down with me opposite Michelle and the guys. We started to kiss and caress each other and I told DeeDee to undress me. She got my shirt off and sucked on my nipples and ran her fingers over my chest. I was fascinated by the feel and weight of her tits and enjoyed myself with them. I felt her undo my belt and pull down my zip. I arched my back and my trousers slid down. I hadn’t bothered with shorts, and as my trousers went down, my cock sprang up. It wasn’t the biggest you had ever seen, but thick and long enough. DeeDee wrapped a hand around me and started to stroke me and I found her now wet pussy Escort Mardin lips and spread her open. I knew Michelle always liked this view and I was sure the guys would not object.

By now, the guys had started to work on Michelle and when I looked over, she had lost her dress and was sat between them wearing a tiny black bra and thong and a garter belt and stockings.

She stood up so we could all see her strip naked. The sight of her black lingerie on her pale skin was electric. DeeDee slowly stroked my cock as I watched Michelle strip and my fingers were working deeper inside her. Naked, Michelle sat back between Bill and Harry and helped them get rid of their clothes. She took a cock in each hand and ran her thumbs over each little eye.

On my suggestion, we moved to the bedroom where we had ordered an emperor size bed big enough for all of us. We spent what seemed like hours mutually groping, sucking, kissing and pleasuring each other, until the time came for some plain old fashioned fucking. Bill was the first as I watched him stick his big black cock into Michelle from behind. I whispered to DeeDee and she scooted underneath Bill’s legs and started to play with his balls and lick his shaft as it pumped in and out of Michelle. I in turn got under her and using her own juices from her pussy, got her ass sufficiently wet to push my cock into her back passage. I can hardly describe how tight and hot it was. I moved slowly inside her at first, building up to a strong regular rhythm. From her response I could tell this was not the first time she had been used this way. Harry, not wishing to be left out stood over the two of us and rubbed his cock over her pussy, slipping it around her clit. I could feel her react every time he hit it. And then I felt his shaft inside her, the two of us separated by a thin layer of tissue. We found our rhythm and began to double fuck her.

There she was, my cock fucking her ass, Harry in her pussy, with a mouthful of Bill’s balls, wanking and licking his cock as he pumped in and out of Michelle. One time, Bill pulled back too far and DeeDee pulled his cock into her hungry mouth tasting both their juices mingling on her tongue. A while later, Bill pulled out again, and this time, DeeDee sucked his cock till it was dripping, then pulled Michelle back to her mouth and did the same to her ass hole. Having got them both lubed up, DeeDee got hold of Bill’s manhood and started to push it into Michelle’s ass.

The hard fucking stopped a little while later as we all took a break. I went and got a few bottles of champagne and poured some over DeeDee. Michelle immediately started to drink it from DeeDee’s breasts, licking her strikingly large nipples. I sucked on her pussy lips as the wine flowed down her body. Not to be outdone, the girls started pouring champagne over Harry and Bills still stiff cocks and drank and suckled from them. This proved to be too much for Harry and as DeeDee leant forward to lick champagne off the end of his cock, a thick wad of cum hit her cheek and slid down her face. More followed as she greedily licked him as his cum went over her lips and trickled down her chin. Michelle joined her and they cleaned Harry’s cock between them. DeeDee positioned herself over Michelle and opened her mouth to let a big gobbet of cum slowly fall off her tongue into Michelle’s mouth. A few minutes later, Michelle returned the compliment and spat the remains of Harry’s cum back into her mouth and DeeDee swallowed it.

Bill was getting close now too. He offered his cock to the two girls and they obliged. The end of his cock was engulfed as Michelle and DeeDee twisted their tongues around him and each other. Michelle was gently stroking him as DeeDee sucked him and then they switched over. Harry and I were groping both the girls as they pleasured Bill. I was under DeeDee, toying with those magnificent tits while Harry had three fingers inside Michelle’s pussy and his mouth wrapped round her clitty. Suddenly Bill arched his back and grabbed his cock, masturbating furiously. The first thick loads hit DeeDee’s nipple and the rest was spread between Michelle’s mouth and neck.

We watched as DeeDee spread the cum around with her fingers at first, and then lifted her breast to her mouth and cleaned it off. Clean herself, she now turned to Michelle and licked the cum off her neck and traced her tongue up to her mouth where she gently licked Michelle’s lips and slid her tongue inside her mouth like a little snake.

Not to be left behind, I felt my own orgasm imminent after all this visual stimulation. I looked for Michelle and she knew exactly what I wanted. She pushed her ass into the air, and DeeDee pushed her cheeks apart and licked her, getting her wet for me. DeeDee held my cock and nudged me against her sweet back entrance until I worked my way in. I played with DeeDee’s tits as I fucked Michelle’s ass and not unnaturally, was ready to shoot my load within a short space of time. I pulled out of Michelle’s ass and DeeDee took me into her mouth. I shot my load onto the back of her throat and felt her swallow as each shot left my cock. As my orgasm subsided, she gently cleaned me with her tongue and when she finished, she looked up at me and we kissed deeply as I mashed her tits against her chest.

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