Haircut

Funny how life gives you opportunities. The trick is to capitalize on these opportunities.

I used to get my hair cut by Jane. Jane is 5 ft 2 cute little fireball. She would always cut my hair in one of the back rooms, so we could tell dirty jokes. At this time Jane was 32 and I was 38. I don't like to brag, but yes, I was easy on the eyes, as women would tell me.

I was married and Jane was recently divorced. There were times when I was sure she was flirting with me. It kind of seemed like she was humping my elbow occasionally as she was cutting my hair. It almost seemed like she was lingering on my elbow, then turned flush. I wondered if she had an orgasm.

The next time I went to get my hair cut, I noticed a big change in her. She now had C cup boobs. Before she looked to barely be a B cup.

As she was cutting my hair, I could feel her boobs brush against my head. Finally, she said, "So, do you notice anything different about me?"

"I don't want to seem rude, but did you get a boob job?"

She laughed, "All the dirty jokes we tell each other, and you are worried about being rude? Yes, I had a boob job. Before I was not even a B cup. Now I am a strong C cup. I finally feel like a woman. Now maybe I can attract a man."

"Jane, you are very pretty. You don't need big boobs to attract a man. But if you are happy, that's all that matters." I told her.

"Aww, thank you Brian. You should feel them. The feel real." She said as she moved in front of me and took my hand and put it on her right breast. I gave her a couple of feels, then took my hand away.

"Yes, they feel very real." I told her.

She took a quick look out of our booth area, then pulled her shirt and bra up and said, "Feel them now."

"Jane, I can't. I am married." I told her reluctantly.

"I want to know, if a guy can tell the difference. Besides my surgeon, no men have touched me yet." She took my hand again and put it on her naked breast.

I massaged her breasts. Her nipple got hard. I played with nipple. Her eyes went close and she moaned. After a good minute I took my hand away. "Yes, they feel very real."

"Fuck, now you made me horny. It's been 2 years since I have been touched by a man." Jane said.

"So, you humping on my elbow doesn't count? If you are really horny, my elbow is available." I said with a smile.

"Fuck, you could tell? Shit, I used to do it to get bigger tips. Now I have my boobs, to tease them with. You never seemed to notice or mind. So, yes, I have had a few orgasms from your elbows."

We had a good laugh. She went back to cutting my hair. I put my right elbow a bit further. She took the bait and stopped cutting my hair and road my elbow to a nice orgasm.

"Thanks for the ride. Please let's keep this a secret." She said.

We finished the haircut and I gave her a very nice tip.

A month and a half later I was due for another haircut. I decided to pull a prank on her. In my jacket I had hid a 12-inch dong. We got to the back room, and she put my cape on. Then went back up to get a different pair of scissors. I quickly got the big dong down my pants and covered up, before she returned.

As she was cutting my hair she asked, "You know, I was wondering, Did you get aroused when I would grind on you?" As she pressed her crotch onto my elbow.

"Funny you should ask. Yes, I would. And I am starting to right now. (She continued to grind even more.) But, I thought about what you said. You finally feel like a woman. I have a very small cock, so I had surgery to making my cock bigger."

With that I pulled the cape to the side a bit showing the bulge of the 12-inch dildo in my pants.

"Holy fuck. It's huge. I let you feel my boobs. Can I feel it?" She asked.

"Sure" I told her.

She ran her hand up and down it and squeezed it. She moved the cape to the side more. This exposed my real cock bulge.

"What the fuck? Two cocks?" She said as she squeezed my real cock and felt it twitch. She jerked her hand away.

I reached inside my pants and pulled out the fake cock. "You weren't supposed to see my whole lap." I told her.

She put her hand back onto my cock. "Still, this is really nice. I want to see it." She told me.

"We can't, what if we get caught?"

"Everyone is gone. It's just us. I will go lock the door." She said as she left the room.

She came back and I was having second thoughts about this, until she came back and started to undo my pants. I lifted my ass up off the chair as she pulled my pants and underwear down causing my cock to pop out right in front of her face.

"Fuck Brian, you have a nice cock." She said, then without warning she straddled me on the barber chair. She pulled her skirt up and started to grind her pussy on my hard cock.

"This feels a lot better than your elbow." She whispered in my ear.

She leaned back and took off her shirt and bra. Jane leaned in offering me her breasts to fondle, lick and suck.

Her hand went to my cock. She pulled her panties to the side and guided my hard cock inside her hot wet pussy. I knew I was not going to last long. Something new, exciting and wrong makes me very excited.

Jane didn't last long. She was over horny and was having a shaking orgasm within two minutes. I thrust 3 more times hard and filled her tight little pussy with my hot seed.

We held each other and kissed for a few minutes before she climbed off of me. I went to pull my pants up when she said, "Leave them down. I want to see your cock while I cut your hair.

She remained topless while she cut my hair. She teased me a lot with her tits during the haircut. This resulted in me getting hard again.

"That is so cool, watching you slowly get hard. It's like you can see every beat of your heart as it fills your cock with blood."

She finished my haircut. "I can't let you go home to your wife with that and the smell of my pussy on your cock." She told me as she got down in front of me and took my cock into her mouth.

Jane had amazing skills at giving blow jobs. It didn't take long before I shot another load into her mouth.

Every month to month and half I would get my hair cut by Jane. We would schedule it after everyone had left. We found some fun positions using the barber chair and the sink. The first 3 times I felt guilty being married. But my wife lost interest in sex 4 years ago.

This went on for 2 years. Then Jane sold her salon. She had a good friend that had started her own business that was growing fast and needed her help. She joined her as an equal partner. That company grew to $200 million in sales. Jane and I never got together after she sold the shop. She eventually found a man and got married.

Fast forward 15 years. I had moved and was working for another company. We were having our annual retreat at a large Resort with lots of meeting rooms.

It was our last day and during our lunch break, a coworker nudged me. "Isn't that Jane H.? She was on the cover of Fortune Magazine last month."

"It is. Watch me hit on her." I told him.

I walked up to her and she suddenly noticed me. "Hey sexy, how about we go to my hotel room and have some fun?" I said with a smile on my face.

"Oh god yes! I want you to dominate me." She said, almost laughing.

My co worker was in shock. "Bill, how would you like to meet Jane? She used to cut my hair."

We all had a good laugh. As we were going back to our meeting Jane pulled me aside. "You know, I think we should have one last good fuck. Can you come to room 604 at 7 tonight?"

"I will be there." I told her and gave her a hug.

I could hardly concentrate during the meeting. Jane was still cute and sexy as she was 15 years ago. Biggest difference was that she was now very wealthy.

I get to her room and lightly knock. The door opens and she is standing there in red sheer lingerie. Her light brown nipples are clearly visible through the bra. I can see light brown pussy hair shaved to a landing strip through the fabric.

As I close the door, she wraps her arms around my neck and we kiss deeply. She is undressing me at the door. I am able to get her bra and panties off. We leave a pile of clothes at the door.

She leads me through her room to the bedroom. She has a large suite with hot tub, balcony, living room and wet bar. We got into the large bedroom with a king-size bed.

In all the times we had gotten together, I never gave her oral. Right now, that's all I could think about was licking her pussy.

I picked her up and put her on the bed. I got on top of her and we kissed deeply. I kissed her neck, her ears.

"Oh fuck, I need you to fuck me so bad Brian. I couldn't even think today. Just thinking about how much I loved your cock in me."

"In time. There is something I always wanted to do with you."

I worked my kissed down to her firm breasts and lingered there, making her nipples hard.

After knowing she was totally aroused, I moved down between her legs. I kissed and nibbled her inner thighs. She was moaning in pleasure. I had always wanted to eat her pussy and I couldn't hold back any longer.

I licked her pussy in long strokes with the flat of my tongue. She tasted great and she was already very wet. I started licking faster, now every so often teasing her hard clit, as it peaked out from its hood.

Her hips started to rise and fall with each lick. I circled my tongue around her clit. She moaned even louder. Her hips began to move faster. I could tell she was getting close. I sucked her clit into my mouth and flicked it with my tongue.

Her legs scissored around my head, holding me tightly. "Oooooooh fuuuuuck!" She screamed as she came hard. She released her grip on my head.

"Good thing you have an end room, we only have one neighbor that could have heard you." I said laughing.

"Actually, I rented the other room next to me for privacy, and why the fuck didn't we do this before? My god, I never had an orgasm like that before."

"Kind of hard to do in a barber chair." I told her.

I moved up and started to rub my hard cock against her wet pussy. Then I slowly entered her.

"Oh fuck, you feel just as good as I remember. Now fuck me like the dirty slut I am." She said.

"Okay, you asked for it. You are my little slut bitch, who happened have her beautiful face on Fortune 500. I bet you men have jerked off to your picture and came all over it."

"Ooooh that is so hot, love to have a bunch of men cum on my face." Jane said as I got her legs over my shoulders and started to fuck her hard and deep.

"You like that bitch?" As I slammed hard into her with my cock hitting her cervix.

"Yes, yes, fuck me, fuck me hard, oh god, I am such a slut." She moaned.

Jane had two strong orgasms before I was ready. "Ooooohhh fuuuuck, I am cummminggg!" I yelled as I just 4 jets of my hot seed deep inside her.

I let her legs down and lay on top of her. I could feel her vaginal walls gripping my cock as she milked a little more cum out of me. This felt so good, that my cock was staying hard. We kissed deeply. I didn't want to pull my cock out.

I rolled over keeping my cock inside her. Jane was now on top in cowboy position. I reached up and started to play with her tits.

"I remember when you had me feel them for the first time. I was thinking, If I tit fucked her, would that be cheating?"

"Do you think that would have mattered after everything we have done?" She asked laughing.

Jane began to slowly grind away, as she was enjoying my cock still inside her.

She started going faster and faster to where she was now bouncing up and down on my cock. Her tits barely moved as they we were as firm as the day she paid for them.

As she was getting closer, I slid my hand down and started to rub her clit for her. It had an instant reaction. Her body stiffened like she was hit by a bolt of lightning. She came instantly. Then collapsed on top of me. I continued to pump and shortly after I came again.

I could feel my seed and her love juices dripping down my cock and into the crack of my ass.

After a bit she rolled off of me. "Brian, I missed this so much. Do you think you can spend the night with me here?"

"We are done with our meetings. I have no plans. I was going to check out in the morning. I would love to spend the night." I told her.

She rolled over and picked up the phone and ordered 2 bottles of champagne, 2 Filet Mignon meals. "I think we have time for one more before the food gets here." She said with a wicked laugh.

Nothing to kinky, just good old missionary position until we both had another orgasm.

Jane got up and got two nice bathrobes out of the closet for us to put on. Then she started the water in the hot tub.

The meal arrived and she gave the guy a $50 tip.

She dropped her robe and took her plate to the hot tub. "Join me for dinner?" She said, as she stepped into the tub.

"Am I eating my steak or that fine pussy of yours?" I said with a big smile.

"Both" was her answer.

We had our plates on ledge and enjoyed our meal and a bottle of champagne. After we were done Jane straddled my lap and we kissed for a good 10 minutes getting reacquainted with each other's bodies, as our hands explored.

We finally broke off the kiss and Jane said, sit on the ledge.

My cock was hard and she put it between her tits. "Is this what you were thinking of, all those years ago." She said then took the tip of my cock into her mouth and swirled her tongue around it.

Jane worked my cock between her man-made tits like a pro. Occasionally she would stop to deep throat my cock.

"Oh fuck, Jane I am getting close. I don't know if I want to cum on your tits or in your hot mouth." I groaned.

Jane didn't give me a choice. She took my cock into her mouth and stroked me until I started to cum. My first load filled her mouth. Then she popped my cock out and continued to stroke me, shooting my hot cum on face and tits. She looked like a mess.

"How's that, I gave you both options. Kind of missed my tits and hit my face on one shot." She said laughing. Then ducked under water and came up all clean.

I slid back into the hot tub and she straddled me again. Seemed weird as we did some catching up talking about kids and our spouses. With her tits rubbing against me occasionally my cock started to wake up. It was now pressing against her pussy, looking to get back inside that nice warm love hole.

Jane leaned forward and started kissing me while she reached down and guided my cock inside her. We slowly fucked inside the hot tub. We slow fucked for a good half hour before we picked up the pace and until water was splashing as we were now fucking hard and fast. We had perfect timing as we had our orgasms at the same time.

We just held each other for a while. "I think we should get out, before we start getting all wrinkled. Then we will look like two 80-year-olds, that like to fuck." I said with a little laugh.

We wrapped the towels around us; Jane grabbed the other bottle of champagne and glasses and led the way to the balcony.

It was warm outside. The stars lit up the sky. It was almost midnight. We hung out at the railing of the balcony talking and drinking. Jane moved a little bit, and her towel accidentally came lose and fell to the ground.

"Oops. Oh well. Nobody can see us." She said and left the towel there.

"You are right. I might as well join you." I said as I took my towel off then stepped behind her and wrapped my arms around her.

I started to kiss her neck and ears. I worked my way down her back. She bent over and spread her legs giving me access to her ass and pussy.

She moaned as I licked her ass and pussy I paid a lot of attention to hitting the right spots. I stood up and guided my cock into her very hot wet pussy. "Oh god, yes, fuck me, fuck me hard Brian, fuck me." She yelled while leaning over the balcony.

She came hard. Just as some lights started to turn on other hotel room balconies. Thing is we were on the top level, and nobody could see our balcony.

She pulled away from me and said, "Wait here, I will be right back."

She returned shortly with a vibrator and some lube. "I wasn't expecting any action, so I came prepared." She said then got down on her knees and started to suck my cock.

"I love how I taste on you.

After a bit, she poured a bunch of lube on my cock, then stood up. Here is something new I discovered, I like my ass fucked." She said, then turned around and leaned over the balcony railing.

I guided my cock towards her ass. With 3 gentle pushes, I entered her tight little ass. "Oh fuck, you feel so tight and good." I told Jane.

"First time I had my ass fucked, I thought, I wonder if I could take Brian's big cock. Fuck, you feel amazing. Now fuck my ass, fuck me hard." Jane demanded.

Jane turned on her vibrator and started to fuck her pussy with it as I fucked her. I could actually feel the vibration. It just added that much more to the pleasure.

I already had a lot of orgasms. I knew this was going to be a long hard fuck before I could cum. I tried to pace myself. But Jane kept yelling, "Fuck my ass, fuck me like a whore." I was doing everything I could to keep up with her. The lights started coming on other balconies again. Only one person yelled, "Shut the fuck up." I think the others enjoyed hearing her.

I think Jane came at least 4 times in the 20 minutes of fucking. I was finally getting close. With 6 hard thrust I just a jet of cum on each thrust.

I collapsed across her back. We were both exhausted. My cock slowly went soft and fell out of her ass. I could some splats of my cum hit the balcony floor. Along with Jane dropping the vibrator onto the floor.

"God, that was perfect and amazing." Jane told me.

"I agree. I don't think I can go again. How about we go to bed and sleep?" I told her.

"I agree, but let's wash off in the hot tub as long as it's there." Jane said.

A quick clean up with a little kissing. We fell asleep quickly with me spooning her.

I woke up hearing a knocking on the door. I was alone in bed. I heard the door open and Jane talking to someone. A bit later Jane came in and said, "Breakfast is ready. Come and eat." She had a robe on, but as she left, the robe dropped to the floor.

We sat at the suite dining table both naked eating. There was some whipping cream on my pancakes. I took some and put it on her nipple, then licked it off. Then some strawberry syrup on the other nipple and licked and sucked on it. With our meal half eaten, Jane took the syrup and put it on my cock. She sucked my cock on and off, adding syrup each time she stopped.

I couldn't wait any longer. I picked her up and carried her to the bed. We fucked in missionary until I came twice.

It was getting close to check out time. We took a quick shower together. Nothing sexual, just washing each other's bodies.

I got dressed and kissed her goodbye. "Jane, this was an amazing time, that I will never forget. Thank you."

"Mmmm, it was the best time in my life. I wish I knew you were here earlier. I love being your slut." She told me as she hugged me.

"Who would ever think, that this filthy rich lady was such a slut in bed." I said laughing.

We kissed goodbye. I went to my room and packed up my suitcase and checked out. Had a nice ride home thinking about our night together. However, I was dead tired when I got home.