The first time I [22M] hooked up with my mom’s shy friend [48F] [MF]

This happened a little over a year ago when I was 21 and she was 47. This was the first of many times I had with my mom’s friend last summer. Using a throwaway account and names have been changed to protect our anonymity. This is my first time posting here but I’ve been dying to tell my story:

My mom’s friend, Jill (48 F), who I’ve known most of my life had gone through a divorce about a year earlier and had just sold her house in the suburbs and moved into a little fixer upper cottage style home about 20 miles away and much closer to the city center than we all live in. Since she knew I (22 M) had been saving money by doing landscaping the last few years, she hired me to clean up her new property and fix some irrigation issues she found out about when she moved in. This was going to be a pretty big project and I’d be working there every day for a couple weeks. This was in the heat of the summer so I almost always had my shirt off when I was doing the work. Most of the day she would be at work when I was there but would come home in the late afternoon just as I was finishing up. She would always come out and talk to me about how the work was coming along and it would sometimes transition into other random topics like my community college classes or gossip from our hometown. I got the distinct feeling she was checking me out and I got a little thrill out of being shirtless while we were talking. It was hard to tell because Jill has always had a pretty shy personality. She is a somewhat nerdy type that is still really sexy. At least she always has been to me. She had curly long brown hair that was slightly unkempt at times. She is tall and thin but a little awkward in her own body and it matches her personality perfectly if that makes sense. Like the type of person that always laughs a little mistimed at a joke and then you can see them thinking about in their own head.

So after several days of these types of conversation I tell her that I’m going out to meet a Tinder date in the city that evening and could I use her shower rather than drive all the way back to our town just to drive back in again. She said of course and I went inside cleaned up and got ready for my date. By the time I was dressed my date had cancelled on me though for some made up emergency. As I walked back through the house Jill was in the kitchen preparing a snack. She was wearing yoga pants, a flowy t-shirt and some Toms style shoes. Have I mentioned I lover her simple style and natural beauty? I mentioned my date being cancelled and this set off a conversation between us where she started opening up to me that she had been thinking about dating for the first time in close to 20 years and how different things are today. She opens up to me that she has actually not been on a date at all since her divorce which kind of surprised me. As we’re talking I’m showing her the Tinder app on my phone (she had never seen it) and we’re getting kind of closer together to where our arms are touching ever so slightly and then more and more pressed against each other as she leaned in to look at my phone. At some point I decide I just want to go for it a little and so I say something like “it’s all pretty easy for hot women like you though”. She let out the most nervous laugh, started to say something, stopped, looked beet red in the face, started talking again and then did the nervous laugh again. I gave a wry smile back but backed away slightly so our arms were no longer in contact. The air was just filled with tension now that you cut practically cut with a knife. I said, “Do you mind if I get a drink” to which she replied with a kind of apologetic tone “Oh, I should have offered before” and turned to the fridge and grabbed a beer for both of us. We were both sipping from our beers and I was doing my best to hold the conversation. She mentioned that she had planned on going to yoga that evening but that “I guess I’ll skip it now” as she held up her IPA and took another sip. She seemed to not know how to keep the conversation going so did my best to keep it up. I told her I had a couple different ideas for one part of her backyard I was working on and I pulled out my phone to show her some example pictures. There was no doubt she had been wanting to get close to me again because she immediately pressed her body against mine again as she stood next to me to look at them. Both our backs were to the kitchen counter arms touching again. The pictures we were looking at on my phone an obvious excuse for both of us to be leaned in close with each other. Our bodies testing the boundaries of how much we could let them touch. I noticed her hair had started to fall onto my shoulder and a little in her eyes. I set my phone down and turned towards her using my hands to push her hair out of her face and behind her ear and I just blurted it out “I’m REALLY wanting to kiss you”. She started to talk but then instead took the tiniest sip from her beer and as she set it down she closed eyes and nodded yes. I leaned in and put my hand gently behind the base of her head and pulled her in started to kiss her first with only lips and then deeper and with tongues.

As we started to make out harder and harder I slid my hand under shirt so that I could feel the skin of her hip and the small of her back. I slipped her shirt up and off of her and she reached back and unclasped her bra. Her breasts were smaller than I imagined them but incredibly sexy. Having only been with girls my own age I was intrigued by the way they fell differently against her body. I kissed first at her neck and then worked my way down to her breasts. As I kissed them and then raised back up to kiss her lip again she began to breathe more heavily. I unbuttoned the first couple buttons of my shirt and she undid it the rest of the way down. Her hands were exploring my chest in a way that made me think I was right about her checking me out shirtless. I said “I’ve wanted this for so long” which had a little different effect that I intended. I think it must have reminded her who I was because she just said “Joy (my mom) can never know about this!”. I assured her that I didn’t want her to know any more than than she did and we were able to pretty quickly resume our making out. At this point we are both shirtless, pressed up against the kitchen counter my hands exploring all the rest of her over her yoga pants and hers feeling my bulge through my jeans. I decided to go ahead and undo the button of my pants and she looked down and then unzipped the rest of the way. She started to slide her hand down my boxers and my cock touched her hand for the first time which caused her to freak out a bit again. She kind of yanked it away and went completely red in the face again. You expect someone that much older to be “experienced” and not nervous but if you knew Jill, this seemed totally fitting to her personality to me.

She kissed me and then immediately said “I’m sorry I’m so weird. Can I try that again?”

“Of course.”

She kissed my neck, my chest, ran her hands up and down my stomach and then dropped down to her knees. She helped me take my pants and boxers all the way down. As my cock came free she let out an “Oh, my god” under her breath and did another one of her nervous gestures before determining herself to keep going again. She started by kissing my legs along the way. Now I was completely naked in Jill’s kitchen. A very strange feeling to see my mom’s cute shy friend on her knees in front of me. She held onto my hard cock so that it was pulled down and stretched out at a 90 degree angle from my body. She kissed just below my belly button. Then lower, and lower until she she was planting kisses right where the shaft of my cock met my body. It was my turn to breathe heavier and she seemed to find her confidence in my delight. She wrapped her hands around my body. One hand on my ass and the other on my hip she pulled my whole body to her pushing my cock deep into her mouth. She licked up and down one side and then the other. Her curly brown hair started to fall all around her face. Without me even asking, she gathered it all and pulled it back so my view was unobstructed. Her eyes were closed and she seemed to be almost in a trance now, clearly enjoying herself. As I stared down I again noticed the difference of her skin from girls my age. Every line in her face was fascinating to me and just made her that much sexier though. I wanted to see every inch of her. I pulled her back up to kiss me and said “let’s go to your bedroom”. She said “great idea” and we started walking, grabbing and kissing as we walked until we fell into her bed together. She peeled her yoga pants off right as we layed down and I kissed her down her body starting at her neck and all the way down to her lower thighs and then back up again until my head was right between her legs. She was so wet it was soaking her inner thighs. I pressed my tongue against her clit and she let out a small moan. The next several minutes I was taking in everything about her, the way she tasted the movements and vibrations in her hips all while exploring up and down her long lean body with my hands. She had also started to guide my head. Her hands running through my hair, adjusting my positioning to just the right spot until she started to quiver and moan. She held me there in place until she came a second time and then pulled my head away and said “Fuck me!” I climbed on top of her and we began kissing deeply again as I slipped inside of her. She pulled me in close to her with both her hands solidly against my upper back digging in a little with her nails. I altered my thrust so that my shaft was rubbing her clit as I went. Her breathing turned to moaning and then near screaming. I used one hand to hold her hips off the bed and the other to get leverage on her hips for deeper thrusts. She shook all over as she came again and then held me in place above her and stopped me from continuing. There was an “Oh my god” and then she exhaled and pushed me off of her and onto my back. She went down on me again and said “I want to taste you” which sent me over the edge. I came hard and I think some hit the back of her throat because she gagged the smallest amount but then swallowed every drop. She came back up and kissed me and rest her head on my chest and we cuddled up nude and basked in the connection.

Source: reddit.com/r/gonewildstories/comments/jkaz9u/the_first_time_i_22m_hooked_up_with_my_moms_shy