Confessions tagged with 'jerkoff'.

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#627

Submitted:

""

I'm 20 years old, not as dumb as people think of me but have let myself be manipulated by an older woman. Paula is 53 and since I was 17 has slowly inticed me into a submissive situation. Its not that I couldn't stop it if I wanted to but I am so used to it I now crave her attention. I was in high school when I first began doing chores for her, mostly painting and cutting grass etc. She is older than my mother, not at all an attractive woman but she always treated me and paid me very well. I lived 8 miles away so she would pick me up and take me home all the time. Her and my mother knew each other slightly and my mother approved of me working for her. She came for me every Saturday morning and would always insist I stay for dinner before she took me back home. It wasn't really like working because she catered to me all the time insisting I take a break often. She began insisting I wear the work clothes she bought for me and before dinner time always insisted I take a shower. I should have known she was a little crazy right from the start but she was so good to me I never questioned her. Only a couple months went by when she would come into the bathroom as I was in the shower. The door didn't lock but I never thought she would do that. The first few times she came in it was very embarrassing and I'd cover my penis with my hands. She began telling me there was no reason for my modesty and in a short time convinced me to let her watch me shower. She said she used to watch her children shower but I found out from my mom that Paula never had any kids. I think I got used to it because she would always give me an extra $10 everytime she watched me. I never told her I knew she didn't have any kids and I'm not sure why but I started likeing it when she was there and often got a hard on. I know I was still 17 at the time when she told me it would be ok for me to masturbate. I was to embarrassed but after a few weeks of her telling me to I finally did as she just smiled and watched me jerk off. After that things got wierd when she started asking if she could wash my back and I wasn't sure I wanted her to but I let her do it. Every Saturday she would wash more of me and as old and ugly as she is it got me turned on when she washed my penis and testicals. I always got a hard on and she would tell me to masturbate and I would. I'm not sure how long it went on like that but then she began jerking me off all the time. I never had anybody do that for me before so I never tried to stop her. She mentioned often that I shouldn't tell my mother that she bathes me but there is no way I would anyhow. I was 18 by then and she began asking if I would stay overnight and she would take me home on Sunday. My mom thought she had extra work for me to do but thats when Paula began giving me massages Saturday nights. I was embarrassed by it the first time mainly because I was laying there naked. She had already jerked me off before dinner and now she was putting oil on me and jerking me off a second time. I still don't understand her but I do whatever she wants me to. I have never seen her naked and she has never wanted me to touch her. I think she has a fetish for young guys and just found out a few weeks ago there is another young guy who goes to her house during the week. I don't stay overnight every Saturday but do most of the time. She gave me her old car last month so now I drive there myself every week. She likes seeing me naked and she likes jerking me off. I think she is crazy but I must be too.

#448

Submitted:

""

A few weeks ago, on Friday, I headed home from work. I was feeling really horny, and, looking forward to an evening of great sex with my girlfriend, Jennifer. As I neared our house, I was disappointed to see her friends cars, parked out front. Her friends, Stephanie and Michelle, had come over, as they sometimes did, to visit. Since they, usually, stayed too long, and, sometimes, drank too much, I guessed that our evening wasn't going to go as I had planned. Once in a while, if they drank way too much, her friends spent the night, and, I knew that would mean no sex at all.

I walked in the front door, feeling more than a little disappointed. I heard giggling coming from the downstairs family room. So, I headed downstairs, to assess the situation. I wasn't surprised to find two empty wine bottles, sitting on the coffee table. But, I was surprised to see the three of them, sitting on the couch, together, in just their bras and panties. I froze, for a moment.

"Take off your clothes!", Jennifer said, as she started to giggle.

I hesitated for a moment, but, since they were in their underwear, I began to do just that. I stopped when I got down to my boxer shorts. I was already half hard, and, had a nice little tent in my shorts.

"Don't stop!", Michelle said.

"Yeah! We want to see it!", Stephanie added.

The three of them kept begging me to take off my shorts, for about the next minute. Until I, finally, decided that if I was going to get any sex, that evening, taking off my shorts was my only option. And, besides, I thought, "Who knows where this might go?"

I pulled my shorts down, and, stepped out of them.

I saw the bottle of astro-glide, sitting next to the empty wine bottles, just as Jennifer said, "I bet the girls you'd jack off for them. They bet you wouldn't. Neither one of them has ever seen a guy jerk off, and, they'd really like to! Will you help me win the bet?"

"No! No way!", I answered, almost immediately.

"Please! Please!", Stephanie and Michelle pleaded. "We'll do anything, if you'll masturbate for us!"

"Anything?", I asked.

"Yes! Anything! Anything you want!", Jennifer said.

"Well, then! O.K.", I heard myself say.

Jennifer smiled, and, tossed me the bottle of astro-glide. I started out, reluctantly, pouring the lube over my cock, and into my hand. At first, I stroked my cock slowly, but, when I saw how hot they were getting, I lost my inhibitions, and, started to pick up the pace. I wound up stroking my cock furiously, until I came longer and harder than ever. My cum spurted all over the place! The girls were very pleased with the show I'd just given them. And, I didn't mind their giggling, whispers, and, smiles.

Then, I reminded them that they'd promised to do anything in exchange for getting to watch. They didn't seem to mind that I suggested we go up to our bedroom.

Once we were in our bedroom, I informed Jennifer that I really wanted to see her eat Michelle's pussy. Without another word, Jennifer turned to Michelle, and started to kiss her. Something about the way they kissed told me that this was not the first time Jennifer kissed Michelle, though it was the first time I'd seen it! They started taking off each others bras and panties. Stephanie was not going to be the only one left with her bra and panties on, and, she started peeling off hers, too. She and I watched as Jennifer and Michelle started to touch each others tits, then, kiss, lick, and, suck. I was in awe, as Jennifer pushed Michelle back on the bed, and, started working her way lower.

I didn't even notice, Stephanie had put her hand on my cock, which was starting to get hard, again, already. And, as Jennifer started kissing Michelle's inner thighs, I, finally, noticed that Stephanie's hand was wrapped around my cock, which was as hard as ever, by then. I pushed Stephanie over, so that she was bent over the bed, and, as I guided my cock into her, Jennifer was starting to really eat Michelle out. I'd always fantasized about getting to fuck Stephanie. I'd never fucked a redhead, before, and, I was in heaven as I started to thrust in and out of her, while watching my girlfriend eat Michelle's pussy.

The three of us wound up spending the whole weekend together. And, I got to fuck Michelle, Stephanie, and, my girlfriend, Jennifer, to my hearts content.

The next weekend, though, as I came home, Friday evening, there were half a dozen cars parked out front. It turned out that Jennifer, Michelle, and, Stephanie had invited more of their friends over. As I got out of my car, I knew what was about to happen.

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