Working to please my (33F) long time mentor (51M) [FM]

Following the overwhelmingly positive responses to my last story, I am excited to write this one. This one is very fresh, and therefore will be in pretty vivid detail (I hope). For the first instalment of my encounters with this wonderful man, check out my post history.

As you might know if you are a frequent reader, I had a surprise encounter with my longtime mentor a few weeks ago. Since then, we have been in regular contact and I can really see us developing into a more regular friends with benefits situation. Neither of us is really in a relationship place, for a few reasons, but I have to admit that the physical chemistry is really outstanding.

So I’ll take you back to Saturday evening after a couple of hours of texting with my male friend. We had decided that he was going to come over to my place for a little bit of fun and some further exploring of the things we had started previously. I took my time and got ready for his visit, showering, making sure everything was perfectly clean, neat and shaven (somewhat unlike last time). I dressed myself in a deep burgundy somewhat lacy, crotch-less push-up teddy underneath a little red dress that showed off as much cleavage as is possible when you’re an A cup. I did my makeup, curled my hair and went to sit in my living room and wait for his arrival.

The crotch-less teddy against my skin was already making me feel pretty hot when the doorbell finally rang. I opened the door and saw that he had put in his full effort into his appearance for our evening as well. The perfectly fitted casual dress shirt and young man jeans (his words, not mine) clung to his frame perfectly, and I knew I couldn’t wait to get them off of him. The front door had barely closed when his hands were in my hair and his lips were pressed against mine, slipping his tongue to me and kissing me deep and slow. He pushed me up against the wall, grinding against me, showing me that he was already hard for me.

He wasted no time letting his hand slip down to the outside of my thigh and lifting my dress slightly before moving his hand to the inside of my thigh and travelling upward slowly. When he reached my bare pussy with the obvious strings from the crotch-less teddy, he slipped one finger between my labia and realised that I was totally soaked for him. He pulled back from me, a look of pure fire on his face and said “fuck this” and picked me up, carried me into the living room and threw me down on my big square ottoman. He dropped to his knees, pulled my dress the rest of the way up and brought his lips immediately to my soaking wet pussy – working my labia, working against my clit, slipping softly inside me, making me moan out his name in pure ecstasy. I gripped the ottoman edges with my hands as he continued to eat me, now bringing his fingers into play as he slowly slipped one, then two inside me to rub my g-spot. At this point I am sure he could tell how close I was getting to orgasmic as he brought his other hand into play, using his thumb to apply just a little bit of pressure against my asshole.

I was done for. Almost immediately I let my moans get louder and my grip on the edges of the ottoman get tighter. My hips shook as an intense orgasm flooded over me. I thought he was going to stop as I had obviously cum, but he kept going, still caressing my g-spot, still licking my labia and clit. At this point the feeling was so intense and I was so sensitive that my moans had turned into full blown screams. As I inched closer to the second orgasm he stopped suddenly and told me that I was going to have to work for another one. At this, I was kind of surprised, and honestly, extremely turned on.

I stood up, pulled my dress off in a couple of quick motions as he undressed himself and stood before me, completely naked, also shaven, and hard as a rock. I instructed him to take my place on the ottoman and I dropped to my knees as he did it. I reached out and grabbed the base of his exceptionally thick cock in my right hand and brought my mouth to the head. I caressed the head with my tongue before completely rolling my tongue around it and taking the first inch or so in my mouth. I remember thinking to myself, “fuck this is thick, I don’t know how I am going to get it all in my mouth”. I did my best to open my mouth and throat as far as possible, and I did better than last time but still, throating this much girth just seems like its going to be impossible for me. Using my tongue I coated his shaft and balls in as much saliva as possible before putting both hands on his shaft and the head back in my mouth. I worked the shaft with both hands in opposite directions and rolled my tongue around the head while sucking (any daddy gang out there will know what I’m talking about).

After a few minutes of listening to his breathing getting heavier and his posture stiffening I released my grip on his shaft and pulled the head out of my mouth. I stepped forward and placed my knees on the ottoman, straddling him. I reached down and guided his throbbing thick cock between my labia lips and slowly lowered myself onto him. The perfect stretch from his girth was amazing and made me feel so full as I placed my hands on his shoulders and he reached up and pulled my teddy down exposing my small but perky breasts and rock hard nipples. I rode him slowly, eventually leaning back and moving my hands to his thighs so he could enjoy the full view of his thick cock inside of me.

As I was starting to feel the pressure of another possible orgasm starting to build within me, he pulled himself to a seated position and wrapped his arms around me. Then he stood up with me in his arms, still inside me. He turned around and again laid me down on the ottoman grabbing my legs and pushing them upward so that my knees were almost touching my chest. He lowered himself on top of me and started to thrust and grind in a circular motion. Now – anyone who’s been fucked like this – you know how fucking DEEP it is. It was so intense because I could literally feel him so far inside me and so thick as his hands explored my chest and shoulders. He was looking into my eyes and moaning my name, all while his thick cock was moving around inside me, grazing my cervix, grazing my g spot.

His intensity was what finally put me over the edge as he continued to thrust and grind on me, looking me in the eyes and holding me so tight. I finally let go and one of the biggest orgasms of my life hit me like a freight train. I screamed his name, panted, shook and my hands grabbed him by the ass to make sure he was as close to me, as deep as I could have him. All of this sent him over the edge and he came hard and fast, deep inside me, moaning my name, panting and staring into my eyes. When he had finished he pulled out of me and lay beside me on the ottoman, totally spent.

Source: reddit.com/r/gonewildstories/comments/syuygs/working_to_please_my_33f_long_time_mentor_51m_fm