Hat Trick

I'd slept with clients before, but it never got this out of hand.

As an interior designer, I'm often the pet of a wealthy matron and this case started out no differently. I should stress that I don't seek out these unions, but I'm single and straight and male. Those are my excuses. Take it or leave it.

Todd and Karen hired me to fix up a small rental unit they owned and that they were now giving to their recently married daughter, Beth. We'd worked together on their three story town house and their 12 room summer "cottage". Now they were calling me in on something that was not up to my usual fare, but as a "favor" to established clients, I looked at the place and gave my fee. Todd reminded me to keep it cheap and then left to a business meeting.

Karen and I stayed behind to discuss the "theme". It didn't take me long to realize that Karen had misgivings about her daughter getting married.

"Can you see me as a grandmother?"

"Well," I said diplomatically, "a surprisingly youthful and beautiful one."

I wasn't lying. Karen was gorgeous in a refined elite way. She was petite and slight, but with a full bosom usually held behind well-fitted jackets. Her pants-suit framed her ass well and gave the impression that nothing was sagging. I knew from earlier conversations that she visited the gym regularly. Add to her fine figure a professional manicure and hairstyle, and you can imagine that I was faced by quite the cougar asking me if I thought she was attractive.

"Karen?" I asked, not answering her question directly but jumping straight to the point,"Is everything okay at home?"

She just smiled.

We moved about the house discussing the kitchen (full makeover), the bathroom (should we leave this as is?--no.), the living room and the bedrooms.

"This should be the master bedroom," I was proposing," with the exit to the balcony and good evening light."

Karen just stared at the ratty double bed that had been left there.

"We'll replace that of course." I commented misreading her thoughts.

"This is where they'll fuck."

What could I say?

"His young stiff cock will stay hard and pummel her for hours."

Karen stared a bit more and then broke the tense silence with a laugh, took me by the arm and led me out the door.

"I'm sorry you heard that, I've become a bit obsessed lately."

"Obsessed or horny?"

"Both."

I prepared plans within a few days and set a time to go over them. As had become our custom during our previous projects, Karen invited me over for a working dinner. Her hobby was cooking and I was always treated to a culinary delight as we reviewed my drawings.

That we were alone with Todd out of the country for three days was not unusual. That Karen served wine was also not altogether out of sync. But when she opened the door in a sleeveless red dress that left little cleavage to the imagination, I had to apologize for wearing jeans.

"Don't worry, we'll take them off later," she said matter-of-factly, turning to hang my coat, and the discussion ended there.

Everything, went smoothly. She liked what I'd done, adding a few pragmatic points. I enjoyed her cooking and said as much. We were sitting opposite one another at their small breakfast table, set for just the two of us. As I threw my napkin onto the table and thought to get up, I felt Karen's bare foot push up the leg of my jeans.

"Are you ready for desert?"

Karen was staring darkly into my eyes and running her tongue across her ruby red lips. At the same time her hands crossed over her chest each reaching the opposite shoulder and throwing aside the stringy shoulder straps they found there.

"Come, Terry, I want to show you something." She stood and came to my side of the table, taking my hand in hers. Her dress slid down and one breast popped out. I admired her bare aureole and pert nipple, but this was not what she'd meant to show me.

Instead, she led me by the hand, seemingly oblivious to the fact that her dress was falling off. By the time we reached the staircase, she had to step out of the dress, but long before that it was clear she had nothing else on. I climbed the stairs behind one of the most beautiful behinds I had ever seen and was straining my eyes to glimpse her vagina between her thighs. When we entered her room, lit by several dozen candles, she turned to me and let me see it all.

"Let me ask you again Terry, do you really find this old lady attractive?"

"Stop calling yourself 'old'." I reproached as I simultaneously leaned in to kiss my shameless matron of the month.

Karen made short work of my shirt, and opened my jeans up just enough to pull out my cock and start sucking. She was doing a fine job at it too.

I'm well built, keeping in shape at the gym and on various job sites. I look rather the outdoors man, not a look you often find in my more genteel line of work. But people appreciate my no-nonsense approach to design. Occasionally, like Karen, they appreciate my 8-inch long and rather thick cock.

I came rather quickly down Karen's throat. Her sucking was fantastic and I enjoyed pinching her nipples and watching her dark hair bob up and down along my shaft. I gave her no warning, but she swallowed my ejaculation like a pro. Then she got up and helped me remove the rest of my clothes.

"How did that feel?"

"Terrific."

"Ready to return the favor?"

"Is the muffin warmed up?"

"Warm and moist."

Indeed it was.

Need I go into the graphic details? We aren't teenagers romping all over the mattress at every angle. Rather two adults, some ten years apart in age. I crossed forty a couple years back and Karen must be mid-fifties though she's far better looking than my miserable ex-wife. She sucked me while I stood, then I kneeled to eat out her cunt. Stroking myself hard as I nibbled at her large clit I was eventually able to penetrate. We fucked missionary style for a few minutes and then I pulled her on top. She wasn't comfortable with that the first few times we fucked, but got used to the idea eventually. By our fourth "work-session" she asked to try doggie style, and liked it.

If we did anything kinky, it was when her daughter's new bed arrived at the apartment. As with all deliveries, I was there to make sure we got the right product and that no damage was done. The delivery team left me to unwrap the plastic wrap and Karen found me there with sheets and towels in her arms. Fucking on her daughter's wedding bed meant nothing to me, but Karen had an intense orgasm and didn't want to stop. When I couldn't go on any more, she pulled a dildo out of her bag and proceeded to fuck her ass. I made a mental note to try and get in that hole myself.

I actually enjoyed the wedding, where I met Karen's daughter for the first time. The bride thanked me for her fantastic new apartment and Todd jokingly reprimanded me for not keeping to the budget. Karen looked suddenly ashamed as I briskly shook Todd's hand. He was beaming with pride and had no clue I was fucking his wife almost weekly. I didn't think he'd care (as long as no one found out). I enjoyed myself, but left early. Karen caught me on the way out and asked if we could slow down a bit. I smiled a knowing smile and told her that she could call, but I wouldn't call her.

Daniel looked me up and down and whistled, making a fuss at seeing me dressed up in a suit.

"Just came from a wedding."

Daniel's the manager at my regular bar. It's where I go to grab a beer and a sandwich when I don't feel like going home alone. The chances of meeting a bed-partner there are slim, indeed almost non-existent. On the other hand, there are a lot of friendly people who enjoy drink, good rock-n-roll, some pool and conversation. We're an older crowd, but the live music shows draw a younger crowd that helps to liven up the place. Tonight was such a night.

I held court at my end of the bar having fallen into an interesting conversation with an ex-Marine and a tourist from Ireland. I also briefly flirted with one of the regular bar-flies. Around one in the morning I was pretty pickled and thinking about heading home. The band was winding down and most of the crowd had faded into the woodwork.

Just then two boisterous young ladies in matching dresses stumbled into the bar. From the color of their chiffon, I knew instantly that we'd come from the same wedding. These two bridesmaids however, had spent more time at the open bar than I had, and were barely standing as they slipped into a booth.

Daniel raised his eyebrows and went over to take their order, but more likely to tell them that he couldn't serve them. In a flash he was back by my side.

"Terry, get this. They want their gowns covered in spunk and just want to suck dick!"

"Why don't I watch the bar while you take them upstairs?"

"Could you do that?"

"Enjoy yourself."

As I said, Dan's Place isn't the kind of establishment at which you'd expect to find hedonistic orgies taking place, but it is a bar, and people do come in looking to let loose. I could sympathize with the young girls' desire to violate their pristine dresses worn for one day only, but didn't want to partake of the promising offer. I would have felt old and awkward. Better to let the young have their fun.

Daniel took the girls upstairs to the office where some of us regulars occasionally went to smoke weed. Derrik, the band's drummer, followed them up assuming that was what awaited. He got a pleasant surprise.

Some twenty minutes later two smiling men and two giggling girls came back down to the bar.

"These girls are pretty wild, man." Daniel whispered to me. I could tell from his mood that he was going to be irresponsible and let the two girls drink. After the bar closed, he even offered some smoke. There are nights like that at Dan's place. Nights I know I should go home after two beers, but stay for a third and don't get home 'till three in the morning. Party nights, when a group of fun-loving kids makes this forty-plus year old feel twenty-five again. These two girls were working their happy magic, going off at the mouth about the wedding, speculating what positions the new couple was fucking in right now, pointing to the cum stains on their dresses and flashing tit to whomever wanted to see. The brunette sucked at least three more cocks. Derrik meanwhile, was working hard on the tall blond, eventually getting her to go home with him. When Daniel closed up, it was just him and me and the chubby brunette named Cheryl who'd passed out on the bar.

"Can you drive man?"

"No, I'll take a cab."

"I walk home, but what do we do with the slut?"

"Cheryl!," I yelled, nudging her and trying to wake her up. She merely mumbled. "Cheryl! Where do you live?!" She barely stirred.

"I can call the cops, but I hate to do that to her."

"I'll take her home, Dan, maybe she'll come to, and if not, then in the morning. But you back me up if they accuse me of kidnapping!"

"Does she have a purse or anything?"

"I take it you didn't think to check ID?"

"C'mon man. You saw what happened. I tried to get them out of here."

"Well she's got tattoos, so she can't be underage."

"Not by too much anyway."

"I'll take her home, you can sleep it off in the morning."

"Thanks man, I'll help you grab a cab."

The cool night air woke Cheryl up a bit and she promptly puked in the gutter. The stains on her dress were no longer just semen.

In the cab Cheryl asked to go home with me as she couldn't go home in this state. My hunch was correct, and Cheryl let me know that she was indeed the bride's baby sister, and only 19. When I told her who I was, she said she'd heard talk of me; that her mom recommended me to all their friends and her dad said I was too expensive. Daniel's hunch was also correct, she was a slut, and half-consciously felt about my crotch.

Arriving home, I suggested she take a shower and sober up then sleep on the couch. I myself went into my room and passed out on my bed. Around five in the morning I woke up and got undressed. My clothes stank of beer and cigarettes and I just wanted to get them off and get me under the sheets, I'd pretty much forgotten about Cheryl. Sometime after that, I became aware of someone getting into bed with me and somehow registered that it must be Cheryl. I reached down to check my balls and realized I was naked. Still the momentary panic wasn't enough to wake me up. I just rolled away.

At 10:08am I opened my eyes and noted the late hour on my alarm clock. Cheryl was sucking my dick. Soon she mounted me and I took in her 19 year old body. Heavy breasts like her mother's, but chubbier around the waist. Her pubic area was shaved and she had a tattoo of a little devil just over her bikini line. She also had tatts on her breast, shoulder-blade and arm. She was a wild one all right.

Cheryl rode me in silence for a while and I watched as her face slowly grimaced into an orgasm. She was basically masturbating with me as a dildo. She rocked back and forth and used her hands to stimulate her clit and breast. Only when the pleasure grew too strong did she fall over me and beg me to fuck her hard. I'm in shape, but after a night of drinking I found the upward thrusts difficult, plus I had a fat tit in my mouth which limited my breathing. So I was rather relieved that she came quickly and rolled off me.

"Sorry, man, I needed that."

"My pleasure."

"C'mon and fuck me. Don't you want to cum?"

"I do and I don't."

"Fuck the 'I know your parents shit', you already fucked that up. Just get on and ride, but don't cum inside me."

She was pretty passive for a bit, but then grabbed my hard-on and helped me decide. I mounted her, spreading her hefty thighs apart and buried my dick in her bare pussy. I banged her hard and fast 'till I couldn't hold out any longer and came in ropes over her stomach and chest. What little landed on her lips, she licked up.

"Mind if I sleep in a bit longer Terry?"

"Be my guest", I called back to her as I headed off to the shower.

Cheryl stayed for two more days, then disappeared. I enjoyed the teenage sex which became more lively once we were both recovered from our hangovers. She had this idea that we had to have sex in every room of the house. I was happy it's a small flat.

I'd almost forgotten the whole episode when a few months later Karen called me up. Todd had bought a new unit to rent out. Something in one of the new towers that had gone up last year. Could I look at it and give her some ideas?

This time I really felt like a gigolo. I refused to take my hourly fee. The place was brand spanking new and was to be rented out. So what did they need an interior designer for?

Yes I fucked Karen. Twice in fact, once in each bedroom which made me think of Cheryl and her little game. I also made a point of fucking her up the ass. When I came we fell apart, huffing and puffing beside each other on the bed.

"Enjoy may ass, Terry?"

"I'm surprised that you took it so well."

"I've been practicing."

"With Todd or your dildo."

"Well, some with the dildo, but -- and no offense Terry -- I took on a new lover."

"A young stud?"

"He's actually older than me, but fucks like a teenager. I think he takes viagra or something."

"Married?"

"Widower."

"And Todd doesn't know?"

"Fuck Todd. He's gay. Hasn't come out of the closet or anything, but I know he sucks dick at his squash club and golf club and anywhere else he can get some. Wouldn't be surprised if he bought some young cock every now and again. If he thinks fucking me for ten minutes once every six weeks is going to keep me down on the farm, he has another thing coming."

"I guess he does."

"I'm going to fake the lease on this apartment."

"What does that mean?"

"I handle the rentals, depositing the checks and so on. I'm going to put in a fake tenant and write myself checks under a false name. Todd thinks the income is going into Cheryl's -- thats my youngest daughter, you've never met -- trust fund, but it won't and he'll never notice it missing."

"Won't Cheryl?"

"She doesn't even know she has a trust fund. She was a beautiful child, but grew into a real bitch. Not nice to say about your own flesh and blood, but she returned our kindnesses with a foul mouth and bad behavior. We've had to send her into rehabilitation twice, but it does no good. She got tattoos all over her body, sleeps around, and disgraces us at any opportunity. You missed the scene she put on at Beth's wedding, getting drunk and dirty-dancing with her good for nothing cousin Amy. And that after Beth insisted they not be left out of the wedding party. What an embarrassment. Todd had the manager call them a cab and kick them out. She didn't show up at home for three days. Can you imagine where she'd been?"

I wanted to say something right then. I should have, had to have. How would it look later if Karen found out about our tryst and then remembered telling me and that I'd acted dumb? But dumb I acted. Karen "moved into" her new downtown pad where she entertained her widower friend and occasionally yours truly. But thankfully, that too drifted on, and almost into blissful forgetfulness.

I answered the phone on the seventh ring and was out of breath from running up the stairs to my apartment.

"Terry?"

"Yeah...hi...one minute."

"Did I call at a bad time."

"No, just got in, hold on... who is this please?"

"Terry hi, this is Beth Radison, Karen Radison's daughter. You were at my wedding a year ago?"

"Yes, Beth. How can I help you."

"I was wondering if you'd seen Cheryl."

"Who?.. Oh! Cheryl. Your sister?"

"Yeah, have you seen her?"

"No, not at all. Why would I?"

"Well she told me she'd slept at your place after the wedding."

"She told you that?"

"Yeah... don't worry I didn't tell mom."

"I feel bad about not telling your mother, but I wanted to respect Cheryl's wishes."

"I agree. Cheryl said you found her drunk and let her sober up."

"That's right. I heard she went into rehab later on."

"Yeah.. she was doing great, but she dropped off the radar a few days ago. I thought she might have sought you out."

"No, I'm not sure she would even remember where I live. She was here just the once."

"Well, sorry to bother you, but you'll call if you hear anything?"

"Yeah sure."

"Don't call my parents, just me."

"Understood."

"Um, Terry, can I ask you another favor?"

"If I can help."

"Um, I don't think my mother told you, but I signed up to study interior design."

"Is that right?" Shit, more competition.

"Um, yeah, and I need to put together a portfolio. I have some things, but... could I ask you to come over and help me present them properly?"

"Well, I'd be happy to help, but why not bring them here?"

"Oh, yeah, I could do that."

Beth came over two nights later. Cheryl had called, she told me. She had hitched a ride out to California.

We went over her portfolio, and to my honest surprise, she had potential.

"Do you think I'll get in?"

"It's hard to say."

"Tell me honestly."

"You're showing a lot of potential here, and in a number of mediums. Your stuff looks technical, like you took a course or something --"

"I did the course at the Tech school last year."

"Right. So it's technical, but reserved. Not a lot of passion there. This one drawing here, and I pointed to one that she hadn't shown me but was among her papers, this one has something. Like you let yourself go and expressed yourself."

Beth laughed, "That one Cheryl did. It was her wedding card to me."

"Well, Cheryl certainly likes to let go."

"Does it have to mean getting drunk or high though?"

"Not at all. 'High on life' right? The best are just honest with themselves, but that kind of honesty can leave you on the edge. Look at me, divorced, kids don't talk to me. Why? Because I expressed myself too openly, too honestly, without civility or manners."