My former fiance had a sister who cut hair. I ALWAYS paid her for her services since I thought it would be really uncool to take advantage of someone simply because you are dating their sister.
This girl was actually a little better looking than my fiance, but they were both pretty hot actually. I'll call her Diane. I ultimately broke up with her sister and never heard from her again, but I digress.
I usually went to her shop on friday nights since it was quiet and I was not taking time from real paying customers who'd tip, I'd pay her for a cut after shop hours, her idea originally.
Anyway, it was always kind of interesting because I thought that she would be pressing parts of her body into me at unusual times and she usually smelled pretty nice and had a hot little bod, but the thought of the fallout from me misreading this was way to much to want to deal with, plus I was 25 or so and probably misreading it anyway, guys being the klutzes we are.
One friday though I was feeling horny and she was looking really nice, it was warm and she was wearing a blouse that was loose and she had no bra on. She'd come in to cut my hair and I could look right down at her tits, which were nice large b cups with good sized brown nipples.
I could not tear myself away from the free show and was hard as a rock under the smock. I could feel the pre-cum dripping out. I had 'adjusted' myself so my poor dick was not turned back on itself inside my suit pants (having come from work) and was really just enjoying the show and thought I'd need to run home and screw my fiance silly.
Diane then stepped in front of me to cut the front of my hair and rubbed her thigh right onto my rock hard dick and pushed her pussy into my hand which was sitting on my thigh. I was sitting in the chair and could not really 'pull back', and I was kind of surprised but the little brain just enjoyed the rubbing too much for a moment or two before I mumbled a 'sorry.'
Diane kept cutting in that split second while this was happening and then I heard a little 'oh' escape her while I finished my mumbled apology. With the strength provided by my raging hard on, emboldened by her rubbing my dick through my underwear, suit pants, the smock and her clothes, I reached up into her shirt and starting caressing her tits.
I was really scared that she'd freak out and then I'd be totally busted, but she stopped cutting my hair and leaned into me and spread her arms so I could get a good feel. Her station was away from the door behind one of the five foot half walls so we could not be seen from outside the shop. As I said, it was after work, no one else was in the shop and we were going to meet my fiance and her boyfriend for dinner at a restaurant a few blocks away.
So, I just kept feeling her boobs and she was standing there really enjoying it, she had her eyes closed and was just standing there enjoying being felt up. I then leaned forward and starting kissing and licking her boobs, and she started moaning. Her sister could come from breast and nipple manipulation and enjoyed it immensely when we did it, so I guessed it ran in the family.
Diane pressed my head against her chest and I was sucking on one nipple and caressing the other and switching back and forth, and we were doing this for about ten minutes when she shuddered, sighed, and then collapsed on me.
A minute or two later she recovered, thanked me, told me she loves having her breasts played with and that her boyfriend was a leg man who skipped over the boobs or just paid very little attention to them.
She then pulled up my smock and told me that it looked like I was a little uncomfortable. I laughed, and unzipped and pulled out my dick and said something like 'ah, thats better.' In reality I needed to cum really bad.
Diane took my dick in her hand and jacked me for a few seconds that felt like a few minutes. I was sooooo horny that I was gonna splooge into her any moment, when she stopped, pulled her shirt up and told me to 'jerk it on her tits.'
At that point I probably would have done it in the picture window in front of the senior citizen lunch group. My dick was throbbing so hard, but I stood up and it took me about 10 seconds to shoot line after line of sperm all over her chest. This was probably best because she could wipe it up really easy and none of it got on my suit or any place other than her tits, chest, neck and hair.
Diane cleaned herself up, and came back and finished up my hair-cut topless. She then told me she had wanted to fuck me ever since she saw me but could not bring herself to actually do that. I REALLY enjoyed what we did and before we left I sucked her boobs to another orgasm for her. I then went home and did her sister the same way that night! What a DAY! Diane told me that we could never say anything to anybody, and I told her that I'd probably stop paying her for haircuts and she just laughed and told me that she'd take it out in trade!
From that point forward for the next 10 months until I broke it off with her sister, I got my haircut ever four weeks religiously, and every once in a while Diane would call me up to see if I needed a trim! Her sister never suspected a thing so far as I ever knew, just that I looked well groomed all the time! Every time I had a haircut Diane and I did the same thing, more or less, never had intercourse, though Diane did end up jacking me off a few times at my request. She was a one track girl and always wanted me to bring her off using her boobs alone. Not that I ever minded! She'd finger herself every now and then to add to the pleasure I guess, or help herself along, but she never let me touch her twat, and to be honest I never saw it!