Mature Affair Ch. 01

Dylan arrived to pick me up promptly at seven thirty. Dylan is a friend - well, a good friend, with benefits. We've shared many intimate sessions, but tonight I asked him to escort me to a charity gala, I of course promised him a lovely evening.

I opened the door. Dylan looked very dashing in his tux. He's tall and dark and, at 52, is fourteen years my junior. He's a consultant, his kids are grown, and has been widowed for four years. Like me, he gets lonely and horny at times.

We had met on a Friday at a trade show where he was working with a client and I was working the crowd for a water systems vendor. He looked very young, but he seemed interested in my products, and we got to chatting, first business and then about our lives. He did not seem at all deterred by the visibly obvious age difference, and he suggested we continue our conversation over drinks. Drinks became dinner, and by dessert I was telling him about my divorce eleven years ago, and he was telling me about how he'd lost his wife to kidney failure. By the time the check came, I wasn't surprised when he held my hand, or, when we stood up after he paid it, how he kissed me gently on the ear.

I was intrigued, but I'm not a fool. "Dylan, you're very sweet, but I'm not exactly a young single girl. I'm not even a soccer mom."

"I'm not looking for a young girl or a soccer mom," he answered. "I'm not really looking for anybody, if you want to know the truth. I just felt this connection happening. I wasn't expecting it, and I'm sorry if I was too forward."

"Not at all," I replied. "I feel it, too. I'm not uninterested, but I'm also not looking for a relationship at this point. I've been on my own for a long time and I like it that way. It doesn't mean that I don't want a friend who can keep me warm sometimes. Now kiss me again, if you like. Properly, this time." He did. It went on for several seconds, and our tongues began the dance. I don't recall whether it was Dylan or I who opened first.

After that, he drove me home. I invited him in, and he kept me very warm indeed.

The next morning, over coffee and danish, we talked for a long time, discussing what had happened and what, if anything, it meant. We started tentatively laying out the contours of an arrangement, one that would work for us both, hopefully for a long time to come.

Following my divorce, I had been sexually active for a period of time, and had come to enjoy it. But as the years went by, the men became less and less frequent, and I had come to terms with mostly being on my own. With Dylan, I saw that this might be changing, although not in any manner I had anticipated. I needed to figure out what my - our - boundaries were going to be.

Dylan was in agreement. This would be a private friendship. We would not involve our kids, mine now long grown with kids of their own, or other family or friends. We would each remain in our own homes, but would have lots of visits and sleepovers.

We would not be a couple. We might go out socially, and at times we might not. We each understood that there might be occasions where it wouldn't be appropriate for us to appear together, with the age difference and all. We would not be exclusive. On the other hand, it was expected that neither of us would be sleeping around. If one of us chose to step out on occasion, that would be fine. In the meantime, we could call on each other whenever we felt like it, hopefully often, would try to be accommodating, but would understand if the answer was sometimes, "Not tonight, dear."

Since that night, we had been together often, and had thoroughly enjoyed our sexual encounters. Tonight will be a social event, although it will certainly end as a sexual one, and hopefully will allow for some provocative antics along the way.

"Margo, you look stunning," Dylan observed as he stepped inside. I'm not. At least, I'm not pretty in any classical sense. "Handsome" is the word I like to use about myself. Not unattractive to be sure. Features maybe a bit plain. A little large in the hips and breasts, but not overly so. Curvy. Short dark hair, styled with bangs, with just touches of gray that I don't color yet, to provide some gravitas in the business world. It keeps men from asking me to fetch coffee at meetings. Tonight I'm wearing a burgundy gown that's spray painted on, low cut, showing a lot of cleavage, sleeveless with bare shoulders, and a high slit up the side, putting my curves most definitely on display. No underwear. At Dylan's request early on, I don't shave anything other than my legs. All in all, a bit much, maybe, for a woman my age, but I'm hoping to have some fun this evening. I like my assets and I still know how to use them. Tonight, I hope to put them in play and stir up, if not some trouble, at least a little intrigue.

"Thank you," I told him. I picked up my clutch from the table, checked for the tickets, and we walked to his car. As we walked down, I put my hand on his back and let it slide down to his bottom. Dylan chuckled softly at this gesture, he knows me.

We arrived at the hotel ballroom, checked in with our tickets, and found places at our table, then went off to the bar for cocktails. Drinks in hand, we took a leisurely stroll around the room, stopping at stations to taste hors d'oeuvres, and looking for friends or acquaintances. We didn't see any. We walked past a couple, about my age. Both were a little on the heavy side. She was marginally pretty, and he was nice looking although balding on top. The man pointedly looked at my cleavage as he went by. Rudely obvious. Someone to have a little fun with later on, perhaps.

The band started and I led Dylan onto the floor. We danced, and he held me tightly, sliding his palm down my back, to my ass. Just for a moment. He flashed me a grin and I squeezed him tighter. I laid my head on his shoulder and he breathed gently into my ear, sending a tingle down to my toes, by way of all the good spots. We danced a couple of numbers, teasing each other here and there, then walked back to our table where a group of three ladies, pretty and in their thirties, were standing around chatting about reality shows.

Introductions were made, and I turned to Dylan. "Be a dear and get me another drink," I whispered.

He turned to walk off to the bar, and Young Lady One mentioned, "He's handsome. Are you two married?"

"Oh, no," I replied, "I'm just keeping him around for the sex." As the Young Ladies grinned, I reached up to touch my earring, in the process intentionally exposing a thick tuft of black armpit hair for all of them to see. In spite of themselves, they stared for a moment before recovering. "Oh," I went on, as if caught by surprise. "He likes that. Or, he says he does. He seems to enjoy places where I haven't shaved."

Young Lady Two responded, hesitating, "It's very exotic, isn't it?" Well, for their generation, I suppose it is.

"That's what Dylan says," I went on. "And I like to keep him happy. He's very, well, accommodating. And, I shouldn't say this, but he's two of most men, if you know what I mean." Three pairs of eyes lit up at that.

Dylan arrived back with fresh cocktails. "Thank you, darling," I whispered, placing my hand on his forearm as I reached to take the glass.

"Always a pleasure," he replied. As I took the glass from him, Dylan let his hand drop brushing my hip. I smiled to let him know that things were going well with the Young Ladies, who were trying to look at his crotch unobtrusively. Their husbands walked up momentarily as dinner was announced, and we all sat down. Young Lady Two sat next to Dylan on the other side.

The dinner was not bad for this kind of affair. Salad, a filet, more or less flavorless, with rice and a vegetable medley. As the meal progressed, I amused myself from time to time by stroking Dylan's leg under the table, occasionally venturing to his inner thigh. At one point, he smiled for no visible reason, so I slid my foot over, very discreetly, to touch his feet. Surprisingly, I encountered an extra foot below his chair. Without a word, Young Lady Two blushed and rearranged herself in her seat.

Dylan lowered his hand to his lap, then covertly slid it over in my direction, finding the slit in my gown and slipping his fingers inside. Upon satisfying himself that I was bare underneath, he withdrew and continued with his meal.

Dessert arrived, then the speeches, thanking all of the benefactors and outlining goals for the coming year. Eventually the band started up again, and Young Ladies Two and Three and their husbands took to the floor to dance. Dylan asked me if I would like to dance, and I nodded yes. Halfway to the floor, however, I stopped him and leaned in close. "You might find some of those women hitting on you tonight. It's your decision, of course, and do whatever you like, but you might want to consider not fucking any of them."

"Why?" he asked.

"Well," I went on, "you might say I oversold the package."

"What did you tell them?" he asked, in a mock menacing tone.

"I wasn't crude or anything. I merely inferred that you are excessively well endowed. I think my comment could reasonably be construed as obliquely referring to ten or eleven inches hard."

"You know I don't have that!" Dylan whispered loudly.

"Yes," I countered, grinning. "I know it, but they don't."

"What did you have to do that for?" a hint of real irritation appearing in his voice for the first time.

"Darling, I love your cock. It's nicely large and you satisfy me perfectly with it. I'm just having some fun with those empty-heads. I enjoy mind-fucking with them. Just go along, let me enjoy myself, and I promise it will be worth your while. Sometimes it's better to keep your pants on and let them wonder."

And with that, we went to the floor to dance. From time to time one of the Young Ladies and her gentleman would come near, and they always stared at Dylan, thinking no one was watching them. Once, Young Lady Three passed nearby, and I ran my hand down Dylan's front, passing just briefly over his crotch before again encircling his waist. Without looking at her, I smiled as if to myself, and reached my hand behind Dylan's neck, giving her another quick flash of my hairy underarm. He squeezed me as we danced away.

After a few numbers, I excused myself. "I'll be back shortly. Why don't you find one of the Young Ladies to dance with?" Dylan walked back toward our table, and I headed to the ladies' room.

I gave Dylan about ten minutes before returning to the ballroom. When I did, he was out on the floor dancing with Young Lady Two. She had both arms around his neck and her body was pressed against his. Tightly. Discreetly trying to judge, I guessed, the truth of my earlier comments and the bulk of what might be down below. I looked away from the dance floor, and saw Mr. Cleavage standing alone. Time for some fun and a little mild revenge. I walked up behind him and spoke softly, "Didn't I see you earlier?"

He turned and smiled as he recognized me. "Yes, I think so, right after we walked in."

I put my hand on his arm and tried to sound provocative. "You seemed interested. Did you see something you liked? Mr. -?"

"Just George," he replied, "and I did. Your gown is lovely."

Liar. It wasn't my gown you were staring at. "Thank you!" I gushed. "Walk with me," I continued, starting toward the empty back of the ballroom, away from the band, the bar and the crowd. When we arrived, I subtly maneuvered George into the corner and stood facing him, so that no one at the party, at the other end of the room, could see anything that might occur between our two figures. "So, you like my dress?" I asked.

"Yes, very much." he answered.

"Let me show you something about it," I went on, taking his hand. I gently brushed it down my side, and then before he could react, I slipped it inside the slit at my hip and planted it firmly against myself. His fingers were in my bush, and he could tell there was no bare skin between my thighs.

"Do you like that? Is that what you wanted?" I teased.

"Mmm yes, that's nice," George replied, his fingertip finding the top of my cleft.

"Is your little thing starting to twitch and stand up?" I smiled and nodded.

He smiled and nodded in return. "Yes, and not so little," he answered, a touch defensively. "I'd like to put it in you, you know." His finger slid a little lower, seeking to part my lips just a bit.

"Mmm hmm," I murmured, and reached toward his crotch as if to feel his bulge through his pants. But I gently lowered his zipper and slid my hand inside his fly. Negotiating through his boxers, I found his penis, fully erect but barely longer than the width of my palm. I ordinarily won't embarrass a man about the size of his cock, but I remembered him staring down my breasts and I tried to make it sting just a little. "That's a hand tool, not a power tool, George," I remarked. "But it still might be good for something." George quickly slid his hand back out from under my gown, and I pulled my own hand out of his pants. I smiled. "Can I tell you what I want you to do?"

"Absolutely," he responded, grinning.

"I want you to go find your wife. I want you to ask her to dance. On the floor, I want you to cup her ass in your hands and whisper in her ear that you can't wait to get her home and slide her out of her dress."

"She'll think something's up. I never act like that." George protested. "We hardly ever do anything anymore."

"If she says anything, just tell her that she looks so fine in her gown, you can't take your eyes off her, and the only thing that's up is your dick," I advised him. "She'll buy it.

"When you get her home, start gently, make out with her, peel her clothes off and take her to bed. Make love to her like crazy. Go down and lick her to at least two orgasms before you mount her and slide it in. By then, she'll be so sensitive that she'll probably come again with you inside her.

"After that, we can arrange to meet sometime and you can tell me how it came out. How does that sound?"

"Sounds great," he replied.

"Good. Give me your phone and I'll put my number in. You can text me when you're ready." I gave George's dick one more discreet squeeze outside his pants, typed in my cell phone number and turned to go find my escort.

Dylan was just coming off the dance floor, with Young Lady Two close by his side. "Having a good time, you two?" I ventured.

Dylan smiled and nodded. "Oh, yes," Young Lady Two replied. "Dylan is a wonderful dancer."

"He is indeed wonderful," I agreed. "Gentle, too. A good thing, he could hurt somebody."

"Why, whatever do you mean?" Young Lady Two teased, her arm still around Dylan's waist.

"Oh, nothing," I replied. "Just speaking out of turn, I suppose." Young Lady Two then smiled and reached up to pat the back of her hair, giving me a full view, as I had done earlier, of her smooth armpit.

"So," I went on. "Would you have any interest in getting together with us sometime, in a more, um, private setting?"

She got the message immediately. She was going to get a chance with that huge cock. "Ooh, that would be lovely."

"Would you like to bring your husband, or come alone?"

"I think I had best come alone," she decided. "If things go well, perhaps we can include him at a later date." She gave me her number and I entered it in my phone.

I reached over for Dylan and drew him away from Young Lady Two's grasp. I nuzzled his ear and led him away. The rest of the evening was uneventful, and after a bit I turned to Dylan. "Take me home and you can show me what all the Young Ladies were dying to see."

On the drive home, we teased each other, with our hands in each other's lap. Inside the house, we kissed deeply and began fumbling with clothes. We finally made it to the bedroom, naked. I took Dylan's cock in my hand and kissed it profusely. He laid me on the bed and went down, pressing his face into my soft pubic curls and parting my lips with his tongue. When at last he mounted and entered me, I pulled him tightly close. He made long, slow thrusts, and when I came, the lights went out and it was like being pounded with powerful waves in the sea, one after another. At last, he gave a cry and flooded my vagina with several convulsions. When he finished, he slowly and gently withdrew and lay down, spooning against my back, his sticky penis between my butt cheeks and his hand holding my breast. We slept.