She had a very pretty face, great tits, and even though she had definitely gotten heavy, she still had a great personality that kept me thinking, “I would love to ask her out,” and yes, I did try to ask her out, but because I either didn’t pursue it strong enough or maybe she didn’t take the hint, it didn’t happen. I had been told, “Never ask you hair stylist out, it’ll ruin your relationship forever.” I didn’t heed the advise.
I had been seeing the same hair stylist for more than twenty years. It started from the time when I was about 40 years old and I think she was about 20. I kept going to her for obvious reason, and it wasn’t just because I got a good haircut. When I first started seeing her, she was a young slender, well built, dirty blonde, that loved to wear low cut tops to show off her tits. She was easy to talk with and came across as someone very personable. With that said, there were many a time when I had thought about asking her out, but either she was in a relationship or I was … in a relationship and even though I had been told, “Never ask your hair stylist out, because it’ll ruin the relationship you have forever,” I continued to think about asking her out whenever I saw her.
Over time though, she moved to a different salon and I ended up trying other stylist. This lasted a few years, but eventually I ended up back with Lisa. I was excited to see her again and I was nervous to see her when I walked in the salon. She was still very pretty, but over the few years when i didn’t see her, she had put on some weight. I’m not sure why, maybe it was the break up with her ex boyfriend or maybe too much partying, or maybe both.
In any case, she still had a very pretty face, great tits, and even though she had definitely gotten heavy, she still had a great personality that kept me thinking, “I would love to ask her out,” and yes, I did try to ask her out once when my … consort was out of town, but because I either didn’t pursue it strong enough or maybe she didn’t take the hint. In either case here I was again, thinking about trying to ask her, because my monthly haircut appointment was coming up and my cherie was out of town. Not heeding the advise of my friend, I wanted to try again to ask her out, but I thought, How can I persuade her to want to go out this time.”
Anyway, as I sat in the chair and she cut my hair, we talked about what was going on in our lives and just like before, I mentioned that my … la petite amie was out of town again. As I tried to nonchalantly explain that she was going to be gone for a week, I said, “Yea, and it’s Friday, and Friday’s a drinking night.”
Lisa simply agreed with my comment and as she continued to cut my hair, I looked at her for a reaction, but continued by saying, “Yea, but I don’t have anyone to go drinkin with.”
Lisa hesitated and then suggested, “Well, you could go to a bar.”
Smiling I replied, “Yea, but it’s a bummer to go to a bar by yourself.”
I knew she went out to the bars with friends, sometimes by herself, but after a pause she again agreed that it was more fun with friends. As Lisa continued to cut my hair I said, “I could go out to a restaurant, but it would feel awkward to go out to eat by myself.”
She again agreed but then Lisa suggested, “How about going to a movie, you could do that by yourself.”
I paused and again said, “I don’t know, it would be nice if I had someone to go with.”
After a pause, Lisa inadvertently blurted out, “I’d go with you,” and giggled slightly.
I didn’t know what to say, but thought, “Was she just making conversation or did she really mean it,” and after a slight pause I said, “Really?”
She paused and said, “Yea, I’d go with you.”
Maybe she didn’t think I’d really go through with it or maybe she felt obligated, in any case I said, “You’re just saying that.”
At first I think she thought I was kidding, but when she saw that I was excited, she realized she needed to try to get out of it, and as she searched for what to say, Lisa inadvertently said, “No, I’d go with you but you know I don’t get off until after 7 today.”
I didn’t want to lose this chance, not now but when I asked, “Well, if you’re up to it, how about going to a movie after you get off work?”
Lisa smiled and pausing again, I think she felt obligated but after stammering for words to get out of going she said, “I would probably need to go by my house first.”
I think she was trying to politely get me to realize she didn’t actually want to do it, but I wasn’t going to let it go and quickly said, “I could meet you at her house.”
Lisa quickly remarked, “No, that’s kind of far to go,” and as she again paused, searching for what to say, she could see my apprehension, which might have made her feel committed to try to go. As she took a deep breath, she suggested, “How about we meet up at this bar down in old town.”
Immediately, I smiled and as I though about it Lisa said, “We could have a couple drinks.”
Elated, I smile and quickly agreed, but I could still sense some reluctance on her part. As she finished my haircut, and I paid her, I felt I needed to make sure she really wanted to go, and so I asked if she could meet up there around eight o’clock, she thought about it for second or two, eventually agreeing and said, “I’ll text you as I head over there.”
Lisa seemed to realize she was compelled to go, and as I shook her hand I said, “I’ll see you later.”
She still seemed apprehensive but as I let go of her hand, I felt it was going to happen. I couldn’t believe it, but as I went home I thought about what to do. I took a shower, cleaned up, and as I waited impatiently for her to text me. I thought, “What if she texted me an excuse that she couldn’t go,” and I’m sure Lisa thought about it too, but as the time approached for us to meet, I continued to worry.
Suddenly, I got a text, I hoped it was from her and as I grabbed my phone and checked, it was from her and seeing that she was on her way, I became over anxious, and hastily texted her back that I’d see her in a little bit. Quickly, I got in my car and headed over to the bar where we were going to meet. After parking, I started to head in, but then I saw her pulling down the street, and as I saw her park, I decided to wait for her. As she walked up the sidewalk, and saw me, she smiled and eventually gave me a hug, before we headed inside.
We ended up having a couple drinks as we sat there talking, and it seemed she was enjoying being out, but I still felt she was just being nice. After a little bit our conversation lulled and when it did, Lisa suggested, “How about we look for a movie to go see.”
I had forgotten that’s what we were going to do and so we both got on our phones and searched for a movie. We eventually agreed on a movie that was playing at a theater close by, and after I paid the bill, we headed out of the bar. I suggested, “How about we take one car,” but Lisa said she wanted to drive herself.
I agreed and as we parked next to each other at the theater, we headed inside. After getting our tickets and stopping by concessions to get some stuff, we went in the actual theater where the movie was playing. As we turned the corner, we decided on seats kind of in the middle, and as we settled in, we continued our conversation from the bar as we snacked on popcorn and soda.
As the lights dimmed, we sat back, and as the movie started, I thought about putting my arm around her or reaching over to hold her hand. I was apprehensive, and instead rested my arm on the arm rest, hoping she would take my hand.
I didn’t know what to do; I wanted to make a move but didn’t want to come across as overly brazen either, and so I decided to just sit back and enjoy the movie, hoping that Lisa might make a move, but she didn’t.
Part way through the movie, there was sudden part that startled both of us. As we shot back in our seats, Lisa jumped toward me and grabbed my arm, pulling me close. We smiled at each other in the dark and as she sat back in her seat, I casually tried to put my arm around her, but immediately Lisa grabbed my hand and as she looked at me, she moved my arm from around her saying, “Sorry.”
“What had I done,“ I thought, but as I again rested my arm on the armrest, Lisa suddenly took my hand, squeezing it gently.
I felt a little relieved that she was still comfortable with being there with me, but as the movie ended and the lights went up, she let go of my hand as we stood up to leave the theater. Walking out to our cars, we talked about the movie and as we reached our cars, there was a pause. I don’t know if she was waiting for me to say something, but in either case Lisa broke the awkward silence by saying, “I had a good time.”
Again, I didn’t want it to end, I wanted to have contact with her before we parted, and as I extended my hand to shake hers, Lisa cautiously looked down, but eventually shook my hand. As we let go of each other’s hand, I hastily stepped into Lisa and reaching out, I gave her a big hug. I didn’t want to let go, but as I did, there was another pause as we looked at each other. It was impulsive and I didn’t know what to say or do, but came to the realization our date was over. However, just as I was ready to turn to leave, Lisa asked, “Hey, do you want to come over to my house.”
I couldn’t believe it and as I stood there for a second, Lisa said, “We could have a couple more drinks.”
Shocked but excited, I immediately agreed, and as we smiled at each other, she said, “Why don’t you follow me.”
Of course, I agreed and even though I knew where she lived, I know that’s weird, I tried to follow her closely, not wanting to lose her.
At her house, she ushered me to the living room, and asked if I wanted something to drink as she went into to kitchen. Lisa brought back a couple beers and as we settled into watch a movie on T.V. she seemed more at ease, even though I was nervous.
I still wanted to make a move on her but was afraid that she’d reject me like she did in the theater. Any way, after we each had another beer, Lisa suddenly laid against the arm of the couch, kind of awkwardly to the side. As I looked over at her, she smiled, and before I could say anything, she grabbed my shirt with both hands, and pull me over on top of her, giving me a kiss. She continued to hold me by my shirt and when I asked, “What was that for,” she kissed me again.
Lisa eventually let go of my shirt but I wasn’t going to let it go and when I leaned into her, and we kissed, I reached both hands up, cupping her boobs. She took a deep breath and as we continued to kiss, I could see her eyes were closed, but she pushed her tongue in my mouth.
I had slid off the couch now and as I knelt on the floor, we continued to kiss. I wanted this and as I moved one hand down to her pants, I undid her them, eventually unzipping them too. We continued to passionately kiss and when I tried to hastily put my hand down her pants, she reached down, taking my hand, stopping me. I worried that I had blown it, but after a second of looking at each other, Lisa said, “Let’s go to my bedroom.”
Nodding, I started to get up off the floor as she swung her legs around, and sat up. As Lisa stood up, she grabbed the one side of her pants, keeping them up and as she smiled, she led me to her bedroom.
I was super nervous, and as we entered her bedroom, and we turned to face each other, Lisa asked, “Are you sure you want to do this?”
There was no way I was going to let this opportunity get away, but as I hesitated Lisa took my hand, I looked at her. As we smiled at each other, I leaned into her, and we kissed. Lisa put her arms around my neck, which let her pants start to slip down. As she wiggled her hips, they eventually fell to the floor, and as Lisa kicked them aside, I held her away from me a little. She had a little bit of a poochie stomach and as I look at her soft little white panties, I grabbed her again after kissing her, moved down to suck her neck.
It was making me hard thinking about the possibilities, but then Lisa suddenly went down to her knees. As she looked up at me, she reached out with both hands and started massaging my crotch, and when she eventually looking back down, she undid my pants. I was in deep now and as she gradually started to pull my pants down, I grab my boxers so they wouldn’t go down too as Lisa immediately started feeling on my cock through my boxers. Suddenly, the head of my cock poked out the little flap, which made Lisa look up at me. Smiling, she looked back down, and as she pushed my boxers down on my cock, she was able to expose it a little more as she started to stroke it.
I couldn’t believe it, but as I continued to watch her, I could her quietly saying, “Mmmmmm,” as she took it in her mouth. I put my hands on her head as she slowly start sucking my cock as she rubbed it. Closing my eyes, I thought about cumming but I did want to yet; I wanted to fuck her, and as Lisa changed her position, sitting on her legs, I could feel her occasionally fondled my balls as she suck my cock.
It felt so good but I needed to stop her. Leaning down, I grabbed her by the shoulders, and as I lifted her back up to her feet, she looked up at me and asked, “What’s wrong.”
Nothing was wrong, except that it felt so good I had to stop her because I wanted more. As she gradually stood up, I turned her to face away from me and as I kissed her neck, I felt on her tits. Lisa eventually turned to face me, and as she did, I backed her up against the bed. She smiled and when I again grabbed her boobs and started to feel on them, she put her hands on mine. We continued to kiss and as I tried to pull her top over her head, she eagerly obliged by lifting her arms.
She was wearing a light blue bra with a lacy top and it seemed her boobs were almost spilling out as I again started to feel on them. Lisa then reached back and unhooked her bra, letting it fall to the floor. Her milky white skin and pink little nipples excited me to the point where I leaned down to tongue and suck her nipples.
I wanted this and it didn’t seem she was going to stop me either and so I lifted her onto the bed. Lisa again giggled slightly but immediately tried to pull my shirt over my head. I immediately helped her and as I got it over my head, I tossed it aside. Lisa reached out feeling on my chest and as I eventually leaned forward, I pushed her to her back on the bed. Her legs were spread as I climbed on top of her and as I laid on top of her, I reached down positioning my cock as I pressed it against her crotch. Lisa immediately started to try to pull my boxers off and realizing what she wanted, I lifted up slightly, and reached down with one hand, taking them off. As I threw them aside, I again repositioned my cock as I laid on top of her again, pressed it against her pussy.
As we kissed, I eventually moved to suck her neck and as I continued to move down, I fondled her tits and again tongued and sucked her nipples. Lisa put her hands on my head and as she did, I continued to move down, kissing her stomach. I wanted to see her pussy and as I reached her panties, I looked up at her to see her reaction. Lisa wasp on her elbow smiling at me, and as she laid back, I kissed her pussy through her panties, eventually mouthing it and pushing my tongue in her slit.
I put my hands on each side of her panties and as I started to pull them down, Lisa again leaned up on her elbows. As I looked up at her, I continued to pull them down until I could see her mound and eventually the top part of her slit. I continued to pull her panties off, and as I slipped off the bed, I pulled them down her legs. I paused, gazing at her plump pussy, wanting to be in her. Lisa had trimmed her hair into a narrow strip that ran from the top of her slit toward her belly button.
Smiling at her, I had her move further up on the bed, as I climbed on with her. I grabbed both of her legs,I looked up at her briefly, as I leaned down, putting my head right between her legs. I could see she was apprehensive, but I didn’t stop her to me from indulging as I kissing and tonguing her slit.
She had a fat stomach, fat thighs, and a fat pussy, but I still wanted to be in her, and as I eat her pussy, she was definitely wet, and as I fingered her pussy as I continued to eat her, she gently squeezed my head between her thighs. I knew I was doing it right and as I continued to flick at her clit as I licked her pussy, she reached down with both hands, holding my head, as she continued to squeeze my head with her thighs. Suddenly, Lisa arched her back slightly, and out of breath she asked me to stop as she pulled at my head. She was coming and I continued to eat her pussy, wanting her to experience it. Eventually I stopped, and as climbed on top of her, her breathing was labored.
Lisa was smiling and as I tried to kiss her, I took hold of my cock and tried to it in her. She seemed tight, but eventually as I pushed into her, she told me to go slow as it slipped in. Immediately, I started to fuck her, moving my cock in and out of her as we kissed. It wasn’t going to take long and as she wrapped her arms arm my neck, my thrusts became more deliberate, and quicker, wanting to cum. It felt so good as we continued to kiss, but then Lisa whispered, “Cum in me,” as she moved her hands down, grabbing my ass, pushing and pulling on me, making sure I wouldn’t stop.
I was there, and as I thrust into her I said, “I’m coming.”
Lisa immediately pulled me close and as we kissed, my cock jumped inside her. Gradually, I tried moving my cock in and out as my cum continued to drain into her. I was done and out of breath I tried to keep my cock in here as long as I could, but as it went limp, it eventually slipping out.
As I rolled off her, and laid next to her, Lisa rolled over cuddling against me and said, “That was nice.”
It was more than nice, but as I kissed her on the head, out of breath I told her, “Yea, that was great, thanks.”
She hugged me tight and as we laid there for awhile, Lisa eventually rolled over to get off the bed. She went to use the bathroom and as I laid there, I felt on my cock briefly, relishing the moment. It felt so good and as Lisa came back, I immediately got up and said, “I needed to use the bathroom too.”
Lisa climbed under the covers as I left the room and when I came back, she was beaming at me as I quickly climbed in bed with her. It was late, and as we embraced under the covers, we kissed, until we eventually trying to fall asleep in each others’ arms. I started having conflicting thoughts about what had just happened, and when Lisa eventually rolled over to be more comfortable, I continued to not be able to sleep. I did eventually nod off for a little bit, but when I happened to wake up needing to use the bathroom, I looked over, and Lisa was looking at me. She seemed concerned, obviously thinking about what we had just done, and as I rolled over to hug her, trying to calm her and myself too, Lisa immediately insinuated, “It’s kind of late.” As we continued to look at each other, I said, “Maybe I should get going,” and when she didn’t try to stop me, I knew I needed to go.
I quickly used the bathroom, and as I got dressed, Lisa leaned on her side to watch me. She gave me a sheepish smile as I pulled up my pants, and as I fastened then, I stepped over to the bed. Lisa laid back, and as I leaned over to kiss her, she turned her head, offering me a cheek. Understanding that it was over, I kissed her on the cheek and as I stood up Lisa sat up in bed and reached over, giving me a hug right before I left.
I felt a little ashamed and realized what my friend had told me about not going out with my stylists was true, but I continued to think about the time we spent together and I have got to say, “The sex was beyond my expectations,” and would I do it again, yea I would.