A place to share your sexy stories
By Veliki
#29883
I was home from college on summer break and I needed to get a few pairs of slacks hemmed. We had a family friend who used to do all of our hemming alterations etc. I had known her since I could remember and at the time she was in her late forties.
It was a hot summer day and I made my way to her home . She opened the front door and as usual I got a warm welcome and big hug . She is a short woman , a bit on the stocky side with large breasts. I always liked getting hugs from her because her breasts always felt so good against my chest. She had divorced years ago but I had always heard rumors about how she liked to date various men but never married any of them.

When she opened the door she was wearing a thin white robe and what looked like pajamas under the robe . This wasn't unusual , I had seen her in a robe before as well as in her bra a few times . She offered me a cold drink and we went downstairs to her basement where she had her sewing machine set up. I was wearing these blue terry cloth shorts and a tee shirt , it was the eighties and terry cloth was in . Off of the sewing room was another room with a couch and a tv .

She told me to go put the pants on so she could measure them . I went into the TV room changed , then came back out and she measured them. With the second pair of pants , she stopped and took of her robe because she was sweating. To my delight she was braless under her white pajamas . Even in her late forties her breasts looked so damn good . They swayed in unison from side to side as she moved . When she leaned over , her cleavage was enough to get me hard. As she stood there I couldn't stare but I could clearly see her dark bush through the thin material.

When she was done measuring , she told me to relax and watch some TV until she was done . I think she realized that I could see her breasts but she was too hot to put the robe back on.

I went back into the tv room , put my shorts back on and sat there watching TV . I couldn't help but get a hardon thinking about what I had just seen and knowing that she was in the other room braless with those big hanging mellons poking up against her pajamas.

So I was sitting there and my cock started getting hard straining against my shorts just begging to be stroked . I gave it a few strokes through my shorts but that didn't do the trick . My hormones took over and I convinced myself that I would take it out of the side of my shorts and rub out a quick one . My plan was that as long as I heard the sewing machine working , she would be clueless as to what I was doing .

So there I was stroking away thinking about her big hangers and how nice and bushy her pussy probably was . I had my cock in my hand stroking away like there was no tomorrow, when the next thing I knew she was standing in the doorway with my slacks in her hand. I never heard the sewing machine stop or anything , I had totaly lost myself in masturbation.

I do remember her gasp and then start laughing as she stood there in front of me . I must have looked a mess trying to stuff my cock back in my shorts . I don't even remember cumming but I did , as there was globs of cum on my shirt and the arm of the couch . She handed me a rag to clean myself up . I remember that I stood up and she gave me a hug and and kept saying in broken english " that's ok , that's ok" don't be embarrassed " . I couldn't get out of there fast enough .

I apolgized and left , hoping she wouldn't tell anyone .
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By Thinker
#29966
I can imagine what could happen the next time you came over for some tailoring. She has the ability to do things with the excuse of being a tailor. She can reach into your pants to adjust things and smooth the fabric over your cock. When you begin to get hard, she can tuck your pockets into place and get a touch of the side of your cock too.

She could use the trick of putting in pins to hold the fabric in place. Now she can offer to help you take off your pants so she can make sure the pins do not prick you. By the time your pants are off, your erection will be "on!" She'll be able to tell you that it is alright if you want to take care of it...maybe help!
By ripstar1
#91185
Wow, does that sound like a similar situation that I had when I was home from Univ. one time. Same thing family friend was seamstress and I went over to have pants altered that were given to me. The seamstress/friend was in her 40s and always on the make after her divorce.

Lots of small talk when I got there. She asked me about my meeting girls at college - did I have a special gal etc. Of course over the years prior she had been beat off material for me. I had seen her in underwear and once a bare tit. I asked her about her life. Boyfriend etc. She said nothing serious and that it was tough dating at her age, but guys at work regularly hit on her.

So she has me put on a pair of slacks and stand up on a flat stool. Takes a tape measure, holds the end at the cuff and the other end in her hand up under my balls. She made sure she got the tape all the way up there and moved the back of her hand across my balls a couple times. Bingo! Junior wakes up and gets chubbie. Now she reaches up under my balls again and holds the crotch of the pants and stretches them out and marks where she will hem them.

Well then of course she pins the cuff. Then repeats the process on the other leg only this time her hand brushes against junior who is chubbed up but still facing down my pant leg. Wearing boxers obviously. She makes a "Hmmm" noise. She suggests I slip the pants down so the pins don't come out. I'm not modest so no big deal, but she is going to get an upshorts view. As I drop trou there is nothing but my boxers to hold junior down and he pops upward and she is there face to tip with junior. She looks at me and just smiles and says to put on the next pair of pants.

She says she will be right back and goes up stairs to get something. I go to the other side of the room to put the other pants on. I can't take the sexual tension and pull junior out and give him several soft strokes. I hear her coming down the stairs and quickly put the other pants on, but junior is hard and pointing at the stars.

We have a sip of our drinks and up on the stool I go. Same routine as before only this time it is obvious I am very erect. She is dressed in shorts and t-shirt and I notice that while she was upstairs she took her bra off and her high beams were staring at me. We went through the measuring routine again only this time she even more bold in feeling around my balls. Now it is time for me to lower the pants. In my haste to put these pants on I left junior poking through the hole in my boxers. I lowered my pants and junior was staring at the ceiling.

I was red faced and told her I was sorry but with her hands around my crotch I couldn't help myself.

I am running out of time. I will finish this later.
By ripstar1
#91260
So to continue.....and finish this.

There she is staring up close at junior who is pointing right at her. She looks at me and says let's get back to work. Go put another pair of pants on and I will get us another drink (beer as I remember). We got the pants off and I made no motion to put junior back in my boxers and I got off the stool and she headed up to get drinks.

I went over and grabbed the pants to put them on, but I was so excited I was afraid I might cum when she measured these pants. So I figured why not finish myself in the bathroom and junior would be soft. So I went into the bathroom dropped my pants and boxers and started to rapidly stroke myself to get this done before she returned.

Well, I was now so nervous that I just couldn't get myself off quickly. Before I knew it she opened the door and there I was facing her with my cock in one hand and holding a wad of tissues (to catch the cum) in the other. She tells me I shouldn't be embarrassed that it is natural for guys to get turned on by her AND why are you not saving "that" for me.

I just said this is so embarrassing and you really turned my on and this shouldn't be happening with you a friend of the family. She responds to not worry about it and that this has turned her on also. I know you noticed that I took my bra off for you. She puts her hands on her tits and squeezes the nipples then raises the t-shirt and asks me if like seeing them AGAIN.

Well I left caution to the wind and began feeling her tits as she knelt down and started massaging my balls. I was still nervous and said I don't think I can last much longer. She started gently stroking junior and as I started to cum she directed my cock so I came on her tits. As she milked my cock to get all the cum out and on her tits she says that she knows there is more of that for her. Then she has me wash the cum off her tits and my cock.

We headed back out of the bathroom straight for the couch. She pulled my shirt off and invited me to undress her. I was in dreamland. I knelt down and pulled her shorts down followed by her thong panties. The thong was wet with her juices. I looked at her and took a whiff of the thong and she asks if I would like a taste of that. She laid back on the couch and spread her legs as wide as she could.

I was on that like a bear on honey. It wasn't long and junior was waking up again. We ended up 69ing on the couch followed by us fucking like "as they say Rabbits". I remember this was the first time in several months I had fucked without a condom and it felt sooooo good.

We discussed that this encounter must be kept to ourselves and she assured me that if I wanted we would do this again. I put the last pair of pants on and we went through the routine again. While we were in the process of taking care of the pants a female friend of hers stopped by. We had introductions etc. as she pinned the cuffs.

She reached up like it was a normal thing to do unbuttoned my pants and lowered. What she didn't realize was I had not put my boxers back on. There I was standing on this stool with my cock (red from recent use) hanging out and this 40something MILF I had just met staring in disbelief. A good laugh and some naughty comments were made. I stepped off the stool and proceeded to put my shorts back on with no mention of my boxers that were still on the bathroom floor.

No I didn't have a 3some we three just had a drink and I left to a couple more racy comments. I did end up having a torrid affair with my seamstress for the rest of the summer and a couple more encounters over the next couple years before, get this, she married my uncle.
By ripstar1
#91443
Luckily for me it is true.

My "seamstress", while we were having the affair, admitted sharing the details with the other gal. The other gal said to her she wished she had an arrangement like ours. My seamstress told her, "Keep away from my boy-toy". I always hoped that it might lead to a 3some, but that never happened. She also told me that the two of them had "played around a little together" once, but said they felt weird about it and never did it again. She said it never went beyond touchy-feely.

Years ago I used to post here, but under an old user name. I've searched here since the site was revamped, but couldn't locate any of my posts. I can't even remember what my old user name was exactly.
By Shardog
#91536
Even more incredible. I posted here years ago too. I think the name was USA or something like that.
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