It was a Friday afternoon. I then (19M) picked up some flowers to not come empty-handed. I wasn't old enough to buy a bottle of wine. My (41F) coworker invited me over to dinner. She was playing matchmaker and wanted to introduce me to her daughter. We were around the same age. I was in the living room and heard a little bickering coming from the bedroom. Minutes later, her daughter comes into the living room and apologizes for the evening. She let me know she had plans with friends and that it was nice to meet me. It felt a little sarcastic, but I smiled and returned the gesture. I shook her hand and told her it was nice to meet you as well. 

She walks out the door, and her mom comes in. She apologizes for everything. I didn't have any other plans, so it was all good. I get up and say, "Well, I guess I should get going then."

No, please stay; at least have dinner." She said. Food is already made, which is too much for myself. 

We sat at the dinner table and ate. We talked and laughed at previous work conversations and talked sh*t about coworkers. We were wrapping up dinner. I helped pick up the plates and started washing the dishes. She asked me not to, but I insisted. It was a delicious meal. I had to contribute my part. As I was washing them, she sat on the kitchen counter, drinking her wine and keeping me company. She had on a beautiful red, flowery dress. Nothing tight. Flowy dress with a nice cut on her chest. Exposing the top of her perky fake tits covered in freckles. Conversations kept flowing. I was finishing up. I told her once again. Thank you for everything, and thank you for being so cool. I didn't want to extend my stay, so I told her I should probably get going. She asked if I'd like to stay and watch TV and keep her company. She hates it when her daughter leaves her alone. She was recently divorced and spent most of her time at the gym to escape loneliness. 

She let me know I could get comfortable. Take my shoes off and put my feet up on her sofa. She had throw covers on there for use. She walked into her bedroom to get comfortable as well. She slips into lounge wear. PJ shorts and a matching spaghetti strap tank top. No bra; she sits on the other end of the couch and puts her legs up. I quickly tried to catch a glimpse to see if she was wearing pants, but no luck. She covered herself right away with the cover and covered my legs in the process. We watched a movie. I remember it so well. The Crow with Brandon Lee. Mid-movie, she adjusted her position to lay on my lap. I'm trying my hardest not to get a boner. We get to the credits; she asked if I needed anything. Water, soda, or a drink. She's about a bottle of wine deep. If I were keeping count, about 4-5 glasses. She asked if I was interested in a glass. I asked if she'd be comfortable with it. She pours me a glass. We talk for a little while longer.

She chugs the rest of her wine and tells me she was sorry for her daughter bailing out on us. She said she was hoping we would hit it off. She wouldn't have to worry about me; she would be happy with the outcome and would love to have little mixed grandbabies. I'm Latino, btw. They were Caucasians. I questioned, What do you mean, worry about me? She explained how she has admired my company and that she is grateful. I started working there. She was happy to consider me a friend, and she didn't feel lonely. It got quiet for a second. I replied that the feeling is mutual. "I really needed to hear that," she replied. "I hate feeling like a pervert." I questioned the pervert. yes! She replied, "I love having you around. I love having you come to my office. I get to see that bulge in your pants. I stare at it way too much. And I told myself, "Well, if my daughter likes him, it will put something in my brain, and I won't have to quit my job or get fired for sexual harassment. Haha! I bend over on purpose to try and get a rise out of you! but you're so respectful and look away."

I confessed that I've felt like a creep since the first day I started working. "At first, I'd hang around to see that tight body of yours, but then you turned out to be super fucking cool. So that makes you double-fucking hot and makes me feel like an asshole because you would bend over or lean forward, not knowing I was creeping." Or at least I thought you didn't know. We could have creeped together!" We both laugh uncontrollably. Nervously, she said, "Well." You came all this way. Kept me company and made me laugh. The least I can do is give you my head.

I laughed, thinking it was a joke. "I'm serious," she said. Pulling her top down under her boobs, she gets on her knees and unbuttons my pants. Pulls the zipper down slowly, creating a small, tingly vibration on the top of my cock. She reaches into my underwear and pulls all of me out. begins to kiss my tip. Kissing her way down my shaft. She gets to the balls, grips them at the base, and stuffs them in her mouth, sucking on them. She really focused on my balls. She massaged them, played with them, and kissed them. She rubbed her face on my balls. She took my pants completely off, licked the very back of my balls, and worked my taint with her tongue. She then licks her way back up to where my balls and my shaft meet, and in a split second, she has my whole cock in her mouth. Her age must have given her all the experience, because that was the best head I'd ever received. Her beautiful lips and warm mouth were going up and down my shaft in a rhythmic motion. Zero-gag reflexes. I can feel the tip of my cock in her throat. It wasn't long before I came into her mouth. After I tried fucking her, she turned me down and sent me home.

After that, head became a regular thing. Only head tho. l'd come over 2–3 times a week. She sucked my dick and sent me home. I got to play with her tits a couple of times. I played with her pussy once. I never fucked her. I tried! But she never let me. She was in control every single time. She said she was obsessed with my balls. 

Work was fun! She would hand me her panties while I was in her office and tell me to return them to her later. That was her way of telling me she wanted me to come over so she could receive my milky treat. I would walk around with her pants in my pocket all day. Leaking and turned on. thinking about her and her warm mouth. I got fired for not doing a great job shortly after. She met a gentleman her age, and we lost touch. 10-star head service. I hope she is doing ok. :)