Dirty Confessions - Reveal your innermost secrets.




My wife of 34 years and me are always competing with each other. We make little bets whenever we're out together. Things like, "I bet you $2 you can't get that guy to shake your hand." Shit like that. I once bet her 50 cents she couldn't get a woman in the mall to kiss her. "Well, fuck me," I actually said out loud when she did. Sometimes they get really kinky. Last week at dinner she blurted out, "I bet you $100 you can't get my mom to suck your dick." Then she laughed. She knew I couldn't refuse that kind of challenge but I had to come up with a plan.

Her mom is 72 years old and has been a widow for about three years. She never goes out and doesn't have any friends to speak of. She lives just a few miles from us so we visit a couple of times a week. My wife and I are very open sexually and can talk about anything and even had another woman in our bed a few times over the years. The one stipulation to our bets is that the other one has to see it.

Last Friday night we went over to her mom, Pam's house after dinner. She's not much of a drinker but I brought a couple bottles of wine anyway. I poured the three of us glasses of wine and said we need to make a toast. I lied and told her I got a promotion at work. We're allowed three lies per challenge. We sipped our wine for a bit and I kept our glasses full. Pam didn't notice that we were barely drinking but she had half a glass gone each I filled them up again.

About halfway through the second bottle I noticed Pam was unsteady and almost seemed to want to go to sleep. I got up and walked behind her on the couch and told her she looked tired and started to rub her shoulders. This relaxed her. When she spoke her words were slurred a bit so I knew she was drunk. Not sure if she was drunk enough to drop all inhibitions but I thought it was time to see. I leaned forward and whispered, "Did dad used to rub your shoulders honey?" She shook her head yes. I slowly moved my right hand down past her collar but she didn't flinch. Then I took the chance and put my hand inside her blouse. Her skin was wrinkled but soft and she had big tits like my wife. Inside her blouse I felt her bra and snaked my hand inside it. She still didn't protest. I undid her blouse with my other hand and noticed my wife was watching intently with one hand rubbing her pussy through her clacks.

Pam's bra clipped from the front so it was easy to undo. When it came undone I circled her tit with my right hand and began to rub her nipple. "Honey, doesn't that feel good?" I whispered in her ear. Her eyes were closed and she mumbled yes. She was quite drunk and I knew it was about time. "Come on, honey, let's get you more comfortable," I said and moved her so she was almost laying down on her back with her head over the low arm of the couch. I was afraid she would fall asleep so I leaned down and nibbled on one of her ears. I undid the rest of the buttons on her blouse and tweaked her nipples a bit. She flinched a little but didn't tell me to stop.

Then I went for it. I undid and dropped my pants and put my hands along the sides of her head tilting it back as far as I dared. I leaned over, "now honey, it's time for you to suck my cock like you did last night." Lie number two, but it planted the thought in her head. I put my cock up to her lips and she shook her head no. My wife chuckled at the failed attempt. I was so close I didn't want to lose the bet so I leaned down and tried to sound like her late husband. "Honey, open your fucking mouth and suck my cock or you'll regret it." She said, "OK," and opened her mouth a little. I put my semi-hard cock in her mouth and told her to milk me dry. Within seconds my cock was hard and I was fucking her mouth and pulling on her nipples. I looked and her hand had gone down to her crotch and she was rubbing up and down. Either she had done this before or she knew what I was doing and was putting on a show. I figured she had done this before and was reliving some memories in her drunken state.

I looked over at my wife and gave her that "Fuck you, I won" smile. Her eyes were glued to her mom's mouth around my cock. "Honey, do you want me to cum in your mouth or on your tits?" I whispered. She mumbled something but I couldn't tell what it was so I just kept fucking her mouth until I was ready to cum. The first shot came, then the second. I figured I'd shoot some in her mouth and some on her tits but when I started to pull my cock out of her mouth her hand shot up and held it in. She was actively sucking the cum out of my cock as I finished. She even kept sucking until I had no more cum, either in or on my cock. When I finally pulled out I didn't even need to clean myself off.

I pulled my pants up and just made a money gesture with my wife. She asked if we should put her mom to bed and I said I think we should leave her here on the couch with her blouse open and her bra unclipped and let her wonder about it in the morning. She'll wonder what happened with her clothes opened and the taste of cum in her mouth. We had a pretty good laugh about it on the way home. She was reluctant but pulled the money out of her purse and gave it to me as we headed off to bed. I won again.