On Friday, October 9, 1998, there was a big birthday dinner for my mom at a very nice Italian restaurant in Beverly Hills. I was seated next to her and at some point in the evening quietly asked her what she had planned for tomorrow night. She then proceeded to tell me of what she had planned for the entire weekend and I quickly realized that I had blown it. Everyone else had offered to treat my mother to any number of activities but other than the usual gift-card routine, I had been so busy with my own life that I had forgotten to make plans for her big day myself, and now I knew that things just weren’t going to happen. Fortunately for me she was having such a good time that she didn’t seem unhappy about it.
A couple of days later she told me that she was going to house-sit the following weekend for my grandmother who would be out of town. Actually she just had to check in on the cat but mom intended to spend much of the weekend there anyway. I offered to keep her company on Saturday night, the seventeenth and I’d order a pizza. It wasn’t sumptuous but it was the least I could do. She said okay and that’s where this story really begins.
At some point mid-evening Saturday, I was sitting on the couch with mom. I had gotten a little bored and noticed a deck of cards. I picked them up and began to shuffle. I dealt her a hand just for the hell of it and she asked what I was doing. I simply replied “poker.”
“I don’t want to play poker,” she said rather annoyed. I then grabbed her cards and put them back with the rest of the deck and continued shuffling. About ten seconds later mom offered to change our relationship for eternity.
“You wanna play strip poker?” she asked with an inviting smile. She was being playful and I wasn’t sure if she really meant it. Mom’s often a tease and I’ve never been one to take her too seriously, but with a thrilling feeling running through me just at the suggestion I said,” That might be fun.”
Mom looked a little uneasy as if silently saying to herself, “Oh my God, what have I done.” After all, she was now going to play strip poker, and with her eldest son! I was a little nervous too but acted calm.
“I don’t mind,” I said, and I meant it. Then with a smile added, “I don’t have anything you’ve never seen before.”
She batted her eyes at that and remained silent but was smiling nervously. I said “I don’t have a problem with it. You should see how I was dressed on the beach in Hawaii last summer.”
“I can imagine,” she sniffed. “Wearing your little thong and showing everyone your behind.”
“I don’t wear a thong,” I replied. “But I am rather skimpy. I have an exhibitionist streak in me.” Mom remained silent as if debating the situation.
“Okay!” she exclaimed loudly, up to her own challenge. “Let’s play.”
“We can have a fanny contest,” I joked, to which she laughed.
“You had a cute fanny when you were a boy,” mom said with bright eyes and a smile.
“Still do,” I replied.
She looked away and nodded. “I’m sure you do,” mom said.
“You’re right,” she continued. “A fanny contest sounds good.” Then she let out a huge grin that masked her bouncing nerves. Mom has always been good at hiding her insecurities behind a smile.
I asked her in the course of playing if she wanted to leave her top on. She had a mastectomy almost twenty years ago, and not wanting either of us to be uncomfortable she agreed that her long tee shirt would remain on.
Then we set the ground rules. Mom was wearing slip-ons with no socks, long white pants, panties, and the shirt that was not part of the game. I was wearing sneakers, socks, tennis shorts, paisley briefs courtesy of Frederick’s of Hollywood, and a sweatshirt. Since mom was wearing less that was within the limits of the game I suggested that to make it even, if she lost a hand she only had to remove one shoe while if I lost, I had to remove both shoes and socks. In this way if I lost a second hand I had to remove my shirt. Third lost hand meant my shorts and then finally my briefs. For mom it was easy: first the left shoe, then the right, then her pants and finally her panties. She seemed in a daze as perhaps the realization of what she had suggested was finally hitting her but instead of copping out she just nodded and said “okay.”
Now let me describe mom. Her name is Susan and she’s in her mid-fifties, but easily passes for mid-forties. Mom is about five-two with short blond hair, blue eyes and very fair skin. Her legs and ass were always husky looking, in an athletic sort of way, when I was younger, but several surgeries over the years forced a dramatic diet change and now she has great legs for a woman twenty years her junior, and her ass is truly fine. As for me, I look just like her, with that same baby-faced appearance which is why even at thirty I still get carded for alcohol. It’s true I have thought about mom sexually, which is why I had no problem in accepting her strip poker suggestion. I had no idea how far this would all go but I knew, whatever else happened, things were going to change forever. Maybe that’s why we were both nervous.
Sitting on the couch with her I dealt the first hand and asked what she had. Queen-high. I lowered a pair of sevens and then mom slowly removed one of her shoes. Her eyes were laughing and excited and she was trying hard to contain a smile. She looked me in the eye and I just stared at her with my own little smile. I was trying to exude a self-confidence which seemed to make her that much more edgy. I lost the next hand and mom let out a little sigh of relief.
“Okay!” she barked. Take it off.” I untied first my right shoe and then my left and pushed them off. I then picked up my right leg to role down the sock in as sexy a way as I could. Mom started laughing. Then I did the same for the other sock.
I dealt the next hand and sure enough I lost again.
“Okay!” she yelled, teasing me. “Take it off! Take it off!”
I stood up right in front of her and slowly, seductively took off my shirt with mom commenting on my hairy chest. As I dealt the next hand I noticed my mom smiling because she was winning and not feeling so threatened — yet! When she lost that hand she took off her other shoe and reached out to play footsie with me. I responded as our toes got better acquainted.
After dealing the next hand I noticed I didn’t have a thing. Mom seemed confident.
“What do you have?” I asked.
“Two jacks and two tens.”
I raised my eyebrows and swallowed a little and said, “Okay.” Looking back I’m almost amazed that mom didn’t try and stop me from taking the next step. I stood up right in front of her, looked in her eyes and she was all smiles with her baby blues dancing. She was really enjoying this. I continued my Full Monty routine, unsnapping my shorts and slowly pulling down the zipper. I then warned her about my paisley briefs so she wouldn’t be shocked.
“Why do you wear that stuff?” she said with a little sneer.
I then oh-so-slowly brought my tennis shorts down exposing all of my legs and a slowly growing bulge in my briefs. She noticed it and then looked away. She may have been my mom but this whole thing was now quite a turn-on. I did a little pirouette for her and sat down to deal again. Mom then got quiet and I saw her swallow hard. She knew we were at the moment of truth. Even if she lost she would have to remove her pants. And if I lost! When I looked at my I knew I was safe. I had three jacks. Lucky me. Mom looked nervous but excited. She knew she had a dead hand. She looked at me and then batted her eyes a few times. I then lowered my jacks. Mom tried to control a little laugh and just looked at me. I stared at her as if to say “Well? What are you waiting for?”
Mom then stood up, exhaled, unzipped her pants and dropped them to her feet exposing her creamy white legs for my eyes to devour, which they did from her feet, up her calves, and to her soft thighs. I then motioned for her to turn around so I could view the back of her thighs and calves and the well-rounded, shapely panty-covered ass, which at this point I was really hoping to see. She gave me a nice show. I felt a little twitch in my briefs and knew I was leaking pre-cum in them.
“Last hand,” I said as she sat back down.
“Listen, we don’t have to go any further,” she said. This has been fun.” Ah ha! I thought. I knew it.
“I thought we were going to have a fanny contest?” I asked. “I haven’t shown you mine yet,” I said with a little smile in an effort to get her to relax so she wouldn’t think she was going to lose. I then started dealing before she could cop-out. When I looked at my hand I knew the truth. I saw a two, seven, jack, eight and ten. There was no way I was going to win. I looked at mom and she had a somewhat more relaxed smile. I lost. She batted her eyes at me once again and I asked what she had. Two kings. When I showed her my hand she had an absolute look of triumph on her face.
“Congratulations,” I said. “You win.”
As I stood up to remove my briefs she said I didn’t have to do it but I insisted. She seemed more nervous now then I was. I then turned around and preparing to expose my buns to her, slowly, seductively began removing my briefs. When my ass was naked she exclaimed “Oh wow!” and then laughed. With a burst of confidence she reached out to touch my ass.
“You’re right,” she said. “Your fanny still is cute.”
“Go ahead,” I replied. “Give it another feel.”
She then massaged my asscheeks not at all realizing the affect it was starting to have on me. When I was out of my shorts I knelt down to pick them up and said “maybe you’d like the grand tour?”
With that I swung around to show her my nearly erect cock. Mom let out a gasp and looked away. Full Monty, indeed. With mom trying to catch her breath, I noticed her totally bare legs giving me all the inspiration I needed and I began pumping my cock, quickly getting it to its maximum length.
“I’ll be I didn’t look like this in diapers?” I asked bringing her attention back to my fully erect cock.
She looked at it again, a longer gaze this time, and then back up at me. “No, you didn’t.”
I then bent down to pick up her left hand and brought it to my thigh. She let out another gasp and held her breath. If she really wanted to stop this she could have but didn’t. I then placed her hand around my cock and together we jacked me off, giving her fingers all the precum she could handle. Then I removed my hand to let her go solo. She did too, tugging at my hard cock and developing a little grin. She was starting to enjoy it. With that shot in the arm I removed her hand from my dick, much to the surprised look on her face. I then took a step forward to where the tip of my cock was inches from her mouth.
“Go on,” I said softly. “I want you to.”
As if on cue, mom took my cock in hand and guided it to her mouth. She parted her lips and then I felt the warmth of her wet tongue encircling my cockhead. With that mom took over. She started to suck cock like a pro and I knew I was goi