Bobby's Mom

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Four young men finally get the woman of their dreams.
2.3k words
4.21
153.6k
117

Part 1 of the 2 part series

Updated 06/08/2023
Created 03/16/2017
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Let me tell you about the time we finally got our hands on Bobby's mom.

Bobby is a good friend of mine and there are usually four of us that hang out at his place most weekends. There is a couple reasons for this, Bobby has all the coolest game systems, they have a pool in the back yard and his mom.

His parents split a few years back, never really found out why, and they moved into town shortly after. When they first moved here she was the typical busy mom, not to active and while good looking was not anything spectacular. Just you know, normal.

Not long after starting her new job she started working out like crazy and now- wow. She's pretty tall with long black hair and definitely in great shape, long muscled legs and built super-hot. Great boobs and butt too.

For the last year or so she has been not really showing off but we all got the impression she didn't mind us checking her out. We had all seen more than the occasional side-boob flash or her hanging out by their pool in a sweet bikini. Bobby knew we were always checking her out and I think he got off on it too. He would always tell us about her coming out of the shower with a short towel or listening to her in her room at night on the computer. Guess it was kind of weird but we loved it.

So this was a Friday night and four of us were sitting around downstairs playing a game. Actually we were playing a game and watching porn to be honest. It was this sweet scene where a MILF was getting seduced by two girls our age. There was a lot of squirming and we were quiet but laughing while watching it. I guess it was louder than we thought since we didn't hear her come home. We knew she was at one of her classes and we were distracted not watching the time.

So there we were, four skinny young guys all staring at the tv as these two girls were sucking the tits of this hot MILF. She was really into it, moaning and playing with their hair as hands were running over her tits and down her belly. Next thing we know his mom is walking down the stairs!

I never saw Bobby move so fast. He clicked off the video and brought the game back up while we all tried to act casual while she's standing on the stairs looking at the tv. The way the basement is set up there was no way she didn't know what we were watching, but she didn't say anything about it.

We were all looking at her like deer in the headlights, arm up on the wall still in her workout clothes. The black leggings really defined her amazing legs and ass, and the bra top leaving her belly exposed was way too hot. No one said anything for a moment, all waiting for the explosion. Surprisingly all she said after a bit of an awkward pause was hi to everyone and that she was going to get a shower. Walking back upstairs she turned her head to catch us all watching her ass and smiled.

Once she was gone we were all giggling at the close call and all horney as hell. We knew better than to bring up the video again so just started the game back up. Little while later we hear her getting out of the shower and were joking about how we could find a way to watch her in the bathroom. I don't know maybe we were louder than we thought but after that video and seeing her in her workout clothes we were pretty excited.

Half an hour later were listening to her move around and start coming downstairs. This was pretty surprising since the downstairs is usually just Bobby and us, but we were not complaining. We look over and our jaws all dropped. She had switched out of the leggings and was wearing some really tight shorts with a pink sleeveless shirt long enough to just cover her ass. Hair up in a ponytail and looking at that shirt she wasn't wearing a bra! The wine glass in her hand wrapped the whole package into the ultimate eighteen year old boy's fantasy.

We didn't even pretend we were not all staring and she had this sexy little smirk walking toward us taking a sip of her drink. She walked toward me on the couch and making a shooing motion sat between Mike and I, leaned back and put her bare feet up on the table.

Even Bobby was speechless for a moment and we were all ignoring the game, till we just shook our heads and started playing again. She started asking us what was going on so Bobby told her about the game as we settled down a bit and got into it. She seemed really interested and had lots of questions between sips of her wine. After a bit she finished her glass and went back up for a refill but was back down again right away sitting between Mike and I while Bobby and John looked on.

The second time she came down though she seemed a bit different, at least to me. She was still asking questions about the game but seemed to be looking at us more. I was so distracted I kept dying which was making her laugh. When her hand landed on my leg and squeezed I almost lost my load but tried to act normal. Even better the second time when she had her hand on my leg up higher and left it there for a minute rubbing!

We were still trying to act normal asking her about her day and how her workout was. She said the class was great but that her feet were sore from all the jumping around. Mike and I immediately looked at each other and thinking the same thing offered to massage her feet. Her hand had been on his lap a few times too, we were so worked up any chance to touch this lady we were taking.

Trying to hide our boners we got off the couch and pushing the table back each took a foot. Now neither of us had a lot, or any, experience giving foot massages but we were giving it our best shot. I guess we were kind of bad at it when she started laughing saying we were tickling her but while she was squirming she didn't pull away.

John had moved off the chair and was now sitting beside her on the couch. He was never overly subtle but she didn't seem to think anything weird about him moving over, just smiled and winked at him. He leaned back almost touching her arm while Bobby sat in the other chair watching, trying to hide his lap with the controller.

Then she asked about the video we were watching earlier.

It was like time froze. Mike and I stopped our clumsy massage of her feet and John held himself still against her as we looked at her and Bobby.

He was pretty cool about it though and just told her what it was and laughed. We expected her to be pissed but all she did was look back at the game we had been ignoring. We were even more surprised when she told him to bring the video back up!

Mike and I went back to massaging her feet and running our hands on her calves. She didn't stop us and actually moved her legs apart a bit more making it easier. Her leg was against John who oh so casually had a hand on his lap now caressing her thigh.

Bobby looked nervous but clicked off the game and brought the internet back up to the homepage of the video site. She sat there looking at the videos, us still massaging her feet and legs, telling him to scroll down.

She asked us which ones we liked to watch and we stammered a bit, telling her about the one we were watching earlier and some of the other videos we liked to watch.

I know I was distracted, my hand was rubbing her calves up and down not even pretending to massage. She flexed a bit and not thinking I squeezed the muscle then kept on rubbing. Mike on the other side was doing the same and his hand slipped past the knee a few times. John's hand was now caressing her thigh while watching the TV and her at the same time.

Bobby switched to the next page and she kept asking questions about each scene and what we liked about it. The whole situation seemed unreal but she wasn't stopping us feeling her legs and we were so turned on I thought I was going to explode.

Halfway down the page she told Bobby to stop and click on one of the videos. It was a girl with long black hair lying on a table getting her back massaged by two blonds. The one on the table looked a bit like her and the two blonds were crazy hot, nice sized boobs in tight shirts. We were all quiet watching these two women rub the bare back of the dark haired girl and slowly slide the towel down to massage her ass.

She was staring at the screen as Mike and I kept massaging her calves and thighs. John had his hand on her upper leg and was rubbing back and forth, getting closer to her shorts. We stopped when she leaned forward, still eyes on the screen, putting her wine glass on the table and slid forward a bit more to the edge of the couch. We had her legs stretched out in front of us and were able to run our hands over the whole length. She motioned with her head for John to slide behind her and start massaging her shoulders. He slid in behind her, it was cramped but he's not a big guy and started rubbing her shoulders, neck and down her arms.

None of us had ever been with a woman let alone touch one like this so the whole situation had an unreal feel about it. Bobby was watching amazed as we all sat around his mom, pretending to massage her but really just feeling her up. On the tv the dark haired girl was getting her ass rubbed down with oil and one of the blonds was sliding her hand up the girl's leg and brushing her pussy.

She said something about how this looked kind of interesting, then stood up. We all thought that the fantasy was over but then she laid down on her front by Mike and I, telling us to keep going while she watched the video!

We were shocked but we're not stupid. Mike and I went back to rubbing her legs, slowly brushing her ass like the girls on the video. John started rubbing her back, pretending he knew what he was doing I guess, and then started moving her shirt up. She lifted her body a bit and he quickly bunched the shirt and brought it over her head exposing her whole back. She moved the shirt to be a pillow eyes not leaving the screen.

Mike and I looked at each other with huge smiles and moved up her legs to start squeezing her amazing ass. She gave a moan so we must have been doing something right and arched her back a bit opening her legs a bit more. Feeling brave I ran my hand between her legs and brushed her pussy just like the girl on tv, my first time ever.

John wasn't even trying to massage anymore, just running his hands up and down her back, trying to brush a bit of boob on the side. Mike started rubbing her ass and back too and she let out another low moan. On the tv the dark haired girl was getting her pussy and clit massaged, so I started sliding my hand higher, hoping I was brushing her clit like the girl on tv. Her back arched again and legs opened wider giving me better access through the shorts. I rubbed up and down, trying to imitate the action in the video. Mike and John kept rubbing her back and ass, and Mike was able to slide a hand down on a boob managing to brush a nipple.

That seemed to really set her off. She propped herself up so they could each reach a nipple. The girl on the video had rolled over and was getting her chest massaged by one girl while the other worked her pussy. She was breathing faster, her hips grinding against my hand as the guys played with her nipples. Bobby was watching with his hand on his crotch rubbing his dick through his pants. As the girl on the table orgasmed she started to shake, grinding her wet pussy against my hand. John and Mike both pulled gently on her nipples while she came which seemed to get her off even more, forehead on the floor biting her lip.

After a couple moments she was done and relaxed under our hands. We kept gently rubbing her bare back until she started to sit up. We moved back, our pants bulging with throbbing cocks waiting to see what was going to happen next. She sat back we had our first look at her bare chest as she brought her hands up to run over her head. On the screen the dark haired had a loud orgasm while the blonds kept playing with her.

When she asked Bobby what other videos he liked to watch we thought we had died and went to heaven.

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7 Comments
AnonymousAnonymous9 months ago

Nice fantasy many boys dream of sex with a old woman.

AzdesertcplAzdesertcplabout 4 years ago
Every boy’s dream

Very good story. I think most boys have had an older woman that they dreamed of seeing nude or nearly naked. These boys REALLY got their dream come true.

AlexaDrakeAlexaDrakealmost 7 years agoAuthor
Thanks for reading

Thanks for the feedback, although why does all the negative stuff come from anon writers lol. Glad you enjoyed and thanks for reading. For Connie if your back thanks for the pleasant images your post left *wink*.

Alexa

AnonymousAnonymousalmost 7 years ago
Connie

I enjoy my friends come around and I dress so my tits and ass show. I like watching their eyes light up. When my husband's friends come around I like showing off. I always leave my tits fall out and they like feeling them and doing other things.

SilentEcho13SilentEcho13almost 7 years ago
Liked It

Keep writing, girl!

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