Cherry Poppin' Co-Worker

As a virgin at the age of 23 I had a lot of sexual imagination, and a lot of time to enact the things I imagined while I was masturbating. Now you can only do so much, but I found that by not holding back, I could always make masturbation a very rewarding experience.

One of my favorite subjects of fantasy was a woman from work. Her name was Laura. She's about 5'9" tall, medium but heavy looking breasts, somewhat wide hips from childbearing, a beautiful face, and neck length black hair. But the thing I really found appealing about her was that she was an older woman at age 42, and she had a very sexual foxy aura. In fact I had noticed her looking at me more and more on the sparse occasions I was around her.

So things began to heat up one day when I had to help her out at work. We had a small project that we had to collaborate on. On the third day she took me out to lunch and started asking a lot of personal questions, and by the time we were finishing eating she had questioned me on having a girlfriend, have I been intimate, and a few other things. I knew at this point I was at a crossroads with her. I could either say that I wasn't comfortable talking about this, or I could dive in and ride this out to see what happened.

I decided to dive in. By the end of the day she had asked me to join her at her house the coming weekend on Friday night. Man was I nervous. All I could think about at work the next 2 day was what was going to happen. I ended up getting in a bit of trouble with my boss. By the time Friday arrived I was a nervous wreck. I also had a heck of a time not masturbating as Laura had told me to do.

Friday evening came and I arrived at Laura's house. She answered the door in jeans and a tight white tee shirt. I had never really found her breasts to be great, but this shirt really made look good. She picked up on me seeing that and grinned.

After a great dinner we headed for her bedroom and I found myself dumb with nervousness. Laura coaxed me to relax and started to strip in front of me. Regardless of her older body and wide hips, she looked wonderful. I loved her heavy breasts, and she had some of the sweetest legs I can remember. She helped me undress and we lay next to each other on her bed, petting, kissing, and groping.

After a few minutes of exploring each other she asked me what I wanted to do with her. I told her I always imagined her being in control. I had a lot of fantasies about her and what we would do, but I didn't want to freak her out with some of the more intense stuff. She asked if that was it, I told her no, but I didn't want her to think I was crazy. She told me that she didn't think that would happen, so I told her about my desire to have her fuck my ass with a dildo or some other toys if she had something. She mmm'd at that and told me to go on. I shared with her how I wanted to fuck her in her office at work. She moaned again at that.

She got up and told me to sit tight for a few minutes while she got a few things. I sat nervously and looked around. I knew she was married with kids, but that fact started to sink in. I started to freak out. She came back and told me not to worry. Her husband was never intimate with her any more. She doubted he'd ever suspect a thing.

She showed me what she had brought back to her room. On the bed she lay out 4 things: 1 small dildo that was about 3 inches long and pretty narrow; a very large dildo that was about 8 inches long and about 2 inches thick; and 2 banana squash which were long and of 2 different thicknesses. She also had a bottle of lotion.

She told me to get on my stomach and put my ass in the air for her. I did so nervously, and she pushed my legs apart a bit, giving her access to my cock from behind. I felt her finger spreading cold lotion around my asshole and she massaged around there to help me relax. Finally she pushed a finger in. I told her to use 2 or 3 fingers, I had done this before and knew what to expect. She didn't waste any time and had 3 fingers in my ass right away. In and out she worked them until she though I was ready for something else.

For a moment I sat waiting for her, and then I felt the small dildo go in. I moaned out loud. Damn I wanted this bad. She started to pump it very fast, each time bumping it into my prostate. After a few minutes she told me I was too loose for that one and she stopped.

Not 10 seconds later she crammed the larger of the 2 squash into my bum. It hurt for second, but she started to ram it into and out of my ass like crazy. Instantly I was pushing my ass back into her, anticipating her rhythm. I shouted that I was going to cum if she would just go faster. But instead she sank the squash as far as it would go and just left it there. I looked back and she was looking into my eyes. I pleaded silently with her to let me cum. Slowly she started to pump it again and finally pulled it out.

Next was the big dildo. I was a little nervous about it because I knew it was thicker than anything I'd used before. She helped me to get into a position where she could wear the dildo and fuck my ass with it. She put it on and lubed up. It went in a lot easier than I'd anticipated. She started to fuck my butt wildly and I couldn't help but start to moan really loudly until I finally came all over her bed.

She pulled out and we cleaned up the mess. Well she did more than me, wiping it up with her fingers and licking them clean. Once she was done we headed for the shower.

I started the hot water going and got in before she did. After a few minutes I wondered what she was doing. Then I heard her come into the bathroom, but I heard more than one person. What's going on, I thought. I looked out and with Laura was a younger looking copy of her. Then I remembered her from the picture...it was Laura's daughter. She had a body a lot like her mother, except with much slimmer hips, long legs, and dirty blonde hair. And, as I found out later, she had just turned 19.

Laura introduced us and I had to laugh at the circumstances. Apparently her daughter, Rachel, was going to join us. I couldn't believe it. The hopped in with me and I ended up in the middle of the sandwich. It was a relentless groping session, with most of it being done by the women. I started to kiss Rachel and didn't realize that Laura had left the shower to get the big dildo and put it on. She got back in and with me still making out with Rachel, she started pushing the dildo into my ass again. I grunted and moaned, but Rachel wouldn't let me stop kissing her, instead pulling me to her. I relaxed and started to join in Laura's ass fucking rhythm. Laura pulled me back to her and I leaned back against her breasts and Rachel go her hair wet under the shower head, and then kneeled in front of me.

She proceeded to give me what I thought was a fabulous blowjob. Having never been through such an experience before, it seemed to be awesome. After bringing me near to climax several times she stopped with the oral treatment and stood back up.

Fuck him! Laura encouraged her daughter as she was still pumping the dildo into my ass very slowly, keeping me constantly on high sexual alert. Rachel put one of her legs up on the rim of the shower and pulled my cock towards her and slowly pushed me into her pussy. Good lord what a feeling. She felt soooo tight, and better than and hand job I'd been through. And so it went, Laura was slowing grinding into my ass with her dildo, and Rachel picking up speed on my cock. I unloaded a huge load of cum into Rachel and she followed shortly after with her own climax and squirted all over the shower.

I expected Laura to stop with the dildo but she kept going and I loved it. I leaned back against her again, and started grinding with her rhythm again. My cock started to harden up right away. It felt sore already, and I tried to focus on the pleasure in my ass. I closed my eyes and kissed Laura. Meantime Rachel began giving me a hand job. I was in heaven! These women were the best. After I was back to full erection Rachel backed into me and started to ride my cock with her ass.

Not more than one minute into this we heard a sound outside the bathroom. I panicked and tried to pull off of the dildo, but Laura held me fast and kept her slow grind going, as did Rachel. Then Laura's husband came in. Holy shit! I was soooo scared, but the ladies kept on fucking me. Laura started to fuck my ass harder and I let out a loud moan. She quickly put her hand over my mouth and her other arm around my waist, and shhh'd me in my ear.

Her husband asked what that sound was and Laura just told him she was massaging her sore calves after a long workout. They talked for a few minutes while he was doing who knows what just feet away from us. Laura increased her ass fucking speed and intensity again and I had a hard time not moaning more. She kept my mouth covered though, and I controlled myself. I felt Rachel coming again as her ass tightened up and she started to buck wildly on my cock. I came too as I realized what she was doing, but she pinched my cock off and held it so she could get my cum all over her tits.

Damn, I thought. This was crazy. Laura's husband was in a yard away and I was there fucking his daughter and wife. He finally left and Laura turned me around and started to kiss me wildly. I returned it and started to touch her pussy. I wanted to fuck her cunt so badly. I was so turned on after what just happened that my erection was renewed immediately. She backed me up to the wall opposite the showerhead and put me inside her. We started to fuck like animals until we both erupted into extremely intense orgasm and moaning.

After that things kind of ended and we cleaned up. I managed to sneak out of the house and headed home. That night I hard a hard time sleeping because of a sore ass and cock, but I easily forgot the pain by imagining what could happen next time I had some time around Laura and her daughter.