My Dinner with the Ladies

I was confused, and wanted more information. Maggie said that some of the women also wanted sex from their waiters, but Maggie and Carol would never put me in that spot. She said it may get a little racy, but we will always protect and respect you. Maggie almost begged and said Carol found me to be a great guy, with a great body and that it would mean a lot to her if I agreed. She also said they would pay me a thousand dollars for the night.

The dinner was the following week and I figured it could be different and would result in a great pay day, so I agreed.

We had a simple dinner out on the patio. The girls explained that they were going to be working every night to prepare. I agreed to help get ready. Now that the backyard was all spruced up, I said I would come by each evening.

On Monday I arrived. Maggie was already there. Carol would be a little late since she was meeting a client. Maggie seemed a little embarrassed when she greeted me. I asked why and she said she'd like me to work nude, but felt awkward asking. I said no problem and stripped in front of her.

Now Carol, although looking me over from head to toe, had never commented on my body. Maggie was quite different. She said really admired my build. I have a classic swimmers body with broad shoulders, well-developed arms, chest and stomach, narrow waist and big thighs and calves.

Maggie had me turn around and really made flattering comments about my back and butt. She reached out and squeezed each cheek and commented on how firm they were.

When I turned around I asked if she had rated everything. She actually blushed and said, "Well, I've seen bigger and seen smaller. But I do like the uncut look on you, and the way it goes to one side. Also, I like the little curve you get when it's hard."

And, she added with a wicked grin, "You have great balls."

Maggie then insisted we get to work. I helped with the dusting, vacuuming and general clean up. Maggie put a couple of CD's on and we sort of danced and worked around the house. Maggie also opened a bottle of wine and we both were soon feeling a little silly.

While working Maggie would give my butt a grab or little slap when she went by. She laughed and we were having a great time. Carol came home around nine and a lot of the major cleaning was over. She sensed we were high and said we should take it easy, especially since we were driving.

I agreed and said I was going for a swim to help sober up. I made my way to the pool and dove in. The water was cool enough to begin bringing me down. I heard a voice asking if I wanted company. Maggie was standing on the edge. She still had on her t-shirt, jeans and sandals. I said I'd love it.

Maggie kicked the sandals off and lifted the shirt over her head. She had on a skimpy bra. She loosened the top of her jeans and pulled the zipper down. She turned her back and shimmied out of the tight pants. I could see her small "little boy's butt" that was hardly covered by a thong. With her back to me, she hooked her thumbs in the thong and eased it off. By the lights of the pool, I could see her pale skin and even paler area of her beautiful ass. She reached behind, unsnapped her bra and let it drop. Slowly she turned with one arm across her breasts and the other in front with her hand covering her crotch.

"I'm a little shy," she said.

"Hey, you've seen me naked for days, fair is fair."

She sighed and dropped her hands. Maggie looked spectacular. Her breasts were probably—Ok I asked later—32 A. Her nipples were tiny and dark with a slightly lighter areola. Her bush was as red as her head, but trimmed and shaved to about an inch and a half strip. It was a little too dark to see if you could make out her lips. She dove in and surfaced next to me.

She stood up and said it was a little cold. I looked at her tiny nips that now stood out a good half inch or more and agreed it did look cold. She looked down and laughed and dove under and began to swim the length of the pool underwater. We stayed in swimming about ten minutes and then decided it was too cold and climbed out to get into the spa that was adjacent. As we were getting in the hot tub, Maggie checked out my equipment that was definitely having a shrinkage effect. "I guess it really is cold by the looks of things."

We stayed in the spa for a while just chatting. I confessed I was really embarrassed that first day when she saw me with a hard-on and then I had to face her back at the office. She said at least it stopped her from having to mentally undress me, as she had been doing for the whole month I was working there.

I was surprised that women did that sort of thing. "Hey, you have a great butt in jeans and we were speculating how good you would look."

We got out and realized we didn't bring towels. Maggie grabbed my hand and we ran back to the house. "Let's rinse the chlorine off and then we can get dressed."

She led me to the guest room where she usually stayed and into its bathroom. There was a large shower stall with a glass door. We both jumped in and Maggie turned on and adjusted the water. She spun me around and then washed my back from neck to heel. She spent a lot of time on my butt and kept saying how tight it was. I then washed her back and said I loved how her little butt fit right into my hands. I reached around and took her tiny breasts into my hands. She put her hands on mine and pulled them away.

"How about you wash my hair and then we get out." I took the hint that she didn't want to go further sexually, but still got a thrill by washing that incredible tangle of read curls. As we rinsed one last time, Maggie put her hands on my waist and pulled me to her. She kissed me lightly on my lips and hugged me, pressing her nipples into my chest, and her crotch into mine. I sprang wood and she reached down and pulled it up so that it pressed against her stomach. She kissed me again, but pulled back with I tried to kiss back and use my tongue. She smiled and shook her head. She then reached down and gave me a couple strokes. "I really have to go, but feel free to stay and finish business."

She got out of the shower and left the door open. I stood staring at her perfect ass as it left the room and then was startled to see Carol walk in.

"I think Maggie has a great idea, why don't you help yourself."

Carol was dressed in a long skirt with a slit up to her thigh and a long-sleeved t-shirt. She obviously did not have a bra on and her nipples poked through the thin cotton material. She was carrying two glasses of wine and handed one to Maggie, as the red head came back into the room. Maggie dried her hair and wrapped the towel around her head. She and Carol leaned against the vanity and looked at me. Maggie was stunningly naked and Carol simply but provocatively dressed.

I had never performed in front of anyone, let alone two women.

Carol gestured with her glass of wine as to encourage me. I slowly slid my right hand on my base and eased it up the shaft. With my left, I added a little soap and soon had a lather. I increased both the tempo and the pressure and felt the tension building. Both women were smiling and focusing their attention on my excitement.

I rapidly reached the point of no return and kept pumping while spurting in the shower.

They both put down their wine glasses and applauded.

"Well done, Owen," said Carol. She leaned into Maggie and sighed, speaking softly to her. Turning back to me she said she was going to her room and thanked me for all my work. She told me Maggie had my pay for the day, and said she really appreciated the last few minutes.

She and Maggie hugged and I noticed Carol's hand rest lightly on the tight ass of the tall red head, stroking it gently.

As Carol left the bathroom, Maggie pulled the towel from her head, came over, stepped into the shower and took the soap from my hand. She washed my now limp member, cleaning away any traces of my excitement. I stepped back under the shower and rinsed.

When I finished, Maggie had left the room. I dried off and put on the clothes that were left on the vanity. Downstairs I found Maggie wearing a long caftan and pouring another glass of wine.

She handed me the envelope and said, "Owen, this is for the real work you did today, and not for upstairs. I want to be sure you know we don't think of you that way. It was a pleasure for us to watch you and we both think you are great."

The dinner was on Friday night, and I could barely contain myself all week. I never mentioned anything to Tom during our daily games and dinners. On Friday, I asked for the afternoon off and Tom was happy to oblige. The market was dead and he was leaving early for his beach house.

I went and thought about how Maggie's wanted me to appear. She had stopped by during lunch one day and we shared a tuna sandwich on a bench in the office courtyard.

She explained that since I was new, I might need a few tips. The first was grooming. She said that they were thrilled to see I was not hairy. I had only mild chest hair and nothing on my back. I did have a fairly thick patch at my crotch and some hair on my lower back and ass. Maggie said I would need to do some shaving and trimming, and that she could come by that night to help. I agreed and she said she would give me the rest of the info then.

Anticipating Maggie's arrival I just put on a robe. She came by around 8 and smiled when seeing me nearly naked.

"Let's go to the bathroom and I'll get to work."

I dropped the robe in the bathroom and Sitting on the toilet seat, Maggie took a pair of barber's scissors from her bag. She had me stand on a towel and she began trimming back my pubic hair. It only took a couple touches as she moved my member around until I was hard. She didn't say anything and soon had cut back the thickness to a thin layer. She then asked for a razor and cream. She took a washcloth and soaked the area and then applied shaving cream to my inner thighs and the area between my navel and the top of the patch. She quickly shaped me into a small triangle with sharply defined edges.

She told me to take a shower and then join her in the bedroom. I was surprised to see she had set up a small table with a crock pot on it. She explained it was a waxing set-up. I began to protest, but she cut me off. "Listen, women do it all the time. So, don't be a wimp."

She had me lie on my stomach. She applied the warm wax to the small of my back and pressed some fabric tape into the wax. When the tape adhered, she warned me and then ripped it off. I couldn't believe the intensity of the pain, but it only lasted for a moment. She then repeated the procedure on my ass cheeks, which didn't have much hair to begin with.

When I turned over, she said this is going to be a little harder. She waxed my chest, again with little hair there I was spared agony. She outlined my newly trimmed crotch and made the edges smooth and the inside of my thighs clean.

She then said, now comes the hard part. She cupped my balls and applied the wax and tape. I held my breath and she yanked it off. I screamed, she laughed and then repeated the procedure two more times. When she pronounced me done, she bent over and kissed each ball.

Maggie then drew a bath and poured in some bath crystals she pulled from her bag. She told me to hop in and left the bathroom. She returned in a few minutes with an ice bucket and a bottle of white wine with two glasses. She must have brought them with her.

She poured two glasses, handed me one and rested the other on the top of the hamper by the tub. She stripped and slid into the tub facing me. Picking up her glass, she toasted me and said the lesson was about to begin.

Maggie explained that Carol had engaged a caterer to prepare the dinner and that he would remain in the kitchen. The four waiters, including me, would wear flip-flops and a geeky Chippendale collar and tie. Each of the waiters would take a position behind the two women whom he was serving. He would bring in the food, clear the plates, pour the wine, and do what his women asked. He was not to speak unless answering a question. And, it was definitely not cool to pop a boner during dinner.

Maggie offered that this could sound degrading, but neither she nor Carol meant any disrespect. Since this was Carol's first hostessing, she was obsessing that everything be perfect. She implored me to go along and that she and Carol would not only be grateful, but also would make it worth my effort.

All the while Maggie was talking her small breasts bobbed up and down in the suds. She would reach out to touch my knee to make a point and once or twice rubbed her foot in my crotch. The effect was that I was enormously hard.

Finally, Maggie brought up the "big finale" as she called it.

"For desert, all the waiters come from the kitchen fully erect. The desert is always some sort of ice cream accompanied by sauces and whipped cream. Each waiter offers ice cream, sauce and whipped cream to each of the guests. The guests have the option to use the sauce and cream on the ice cream or on the waiter. Guess which we always choose? So, each woman really has the opportunity to perform some oral sex on each of the waiters. I know this sounds so weird. And, Carol has already said she wants it to be me who cleans the sauce from you. Some day, if we have a lot of time, I'll try to explain Carol's sexuality. But for now realize she'd rather watch than do.

"I know this can be embarrassing, and if you want to back out you can. Carol will claim a client emergency and leave town for a week or two. She will lose face, but we all will survive. She wanted me to be sure to let you know that you've been a great sport up to now and there would be no hard feelings."

Maggie smiled as she rubbed her foot up my erection, "Well, no hard feelings except for this little fella'."

Friday night arrived and I went to Carol's at 7. The other three waiters were there and Maggie started running through the night's menu, the layout of the kitchen and dining room, and other details. She then handed us our "outfits" and directed us to a study down the hall.

Maggie's brother, Mike, was her twin. He was tall and skinny like her with the same red hair. Jake was about my size and looked like an athlete. Marcel was black and the tallest of us all at about 6'3".

We began stripping, and I soon found out that I was the junior member in every category. Mike had a long, thin dick that looked even bigger on his skinny body and surrounded by his close cropped red pubic hair. He was circumcised and had a big head. Jake was Italian and he had the thickest one I've seen. It was longer than mine and much darker. Marcel, however, lived up to the stereotype of a black man. He had a dick that was at least 9", with a big curve to the right. He was uncut like me, but his member was two shades blacker than his skin.

The guys started rubbing a light coating of oil on them. Mike tossed me a bottle and said it looks better with a little sheen. I followed along. Mike offered to do my back and I did his. Each of us also worked his dick so it hung heavier.

Maggie came in and gave us an approving look and told us to meet in the hallway to greet the guests.

The women arrived in pairs. The first were two attorneys about 35. They had short black dresses, stockings and high heels. Jake stepped forward and they each took an arm and he led them into the living room.

Next came a mixed race couple. The black woman was a professional basketball player, whom I recognized. She was taller than Maggie and wore her hair close cropped. She had on a tan silk pants suit and a creamy camisole underneath the jacket. When she walked everything moved seductively. Her companion was a white woman who played on the US soccer team. She was blond, about 5'7" and wore a brown dress that clung to her and let everyone know that underwear was not part of her outfit. I assumed that Marcel would escort them, but Mike stepped forward. They each hugged him and as he walked them down the hall they joined hands and rested them on his ass.

The doorbell rang again and Maggie greeted two women in their forties. I almost fainted when I recognized one as my boss' ex-wife. She often came by the office and we had chatted a number of times. She recognized me, too, and gave me a thorough up and down glance and smiled. She was a blond who looked a lot like Diane Sawyer. She just dripped class, wearing a camel skirt with a soft silk blouse. Her dinner partner was a brunette, whom I later discovered, was a leading surgeon in Boston. She wore all black, silky pajamas with the top three buttons open to reveal amazing cleavage.

Karen, my boss's ex, walked over to Marcel and stood on tip toe to kiss his cheek, while running her hand up and down that huge organ. Her partner did the same. Then Marcel escorted them to the living room.

Maggie and Carol were the youngest of the group, neither one of them were thirty. Maggie was wearing a white, long-sleeved cotton top with her nipples pushing the fabric and fitted black linen pants. Her hair was loosely tied up with a black ribbon and she wore just a trace of make-up. She looked incredible. She took my arm and we headed toward the other guests. As we passed the door to the dining room, Carol joined us. She was wearing a loose pair of black silk pants with legs that billowed and a black top that was completely sheer. I could clearly see her breasts and dark nipples. I felt a rush to my loins and I think Maggie sensed it. She whispered in my ear to cool down. As part of my pre-dinner instructions, Maggie said if I felt myself getting hard, I should get to the kitchen. They kept a bowl of chilled water there and I should stick my dick in it. No boners before their time, was how she put it.

The ladies were chatting and the men took their drink orders. We retreated to the kitchen. In spite of any embarrassment, I headed for the bowl of chilled—it really was iced—water and plunged my equipment in. The effect was immediate, and I lost the urge to grow. A bartender made the drinks while we each took a tray of hors d'oeuvres back to the ladies. They oohed and aahed and took some. I soon realized that touching was part of the ritual. Some would rest a hand on a naked butt or thigh, or rub a leg from knee to groin. Maggie cupped my ass and gave me a light squeeze. Carol, who really never touched me before, brushed the back of her hand across the tip of my dick as she reached for an appetizer. I knew I would soon be back to the ice bowl. The men went to retrieve the drinks. As the new kid, I took the tray and Mike said I had to serve each woman. I had hands everywhere as I made my way around the room. Karen said it was so good to see me and picked up my penis and looked at it. She offered it to her friend, who took it and pulled slightly. I turned to Carol who and smiled. Maggie stood up and asked me to join her in the kitchen.

She told me to soak it again since I was almost past half-mast. I obliged and then rejoined the group. The men stood along the wall next to the fireplace. The women chatted and occasionally would raise a glass for a refill.

When it came time for dinner, we served each course to our individual ladies. Actually, there was a lot to do and after a while I relaxed and forgot about being nude, although Maggie would give me a little butt squeeze every now and then. We cleared the table and it was time for desert.

Each of us waiters took a couple minutes to stroke and get hard, and then moved on to dessert. We each took a tray with chocolate and butterscotch sauce, pureed strawberries, whipped cream, and two bowls of ice cream. Each waiter went to his women and served the bowls of ice cream. Maggie then took the brush that was on the tray and spread chocolate sauce on me. She topped it with a dollop of whip cream and started to lick me clean. Her mouth was so warm, I thought I might shoot. She probably thought the same so she reached underneath and clamped my balls. I got the message.