I'll cliff notes this story some but I had an ongoing sexual relationship with the company presidents secretary - she was in her late 40's, been married since she was 18, and had never fooled around with another man, so it took 6 months of working on her to get to this point, I mean there were quick sessions of heavy petting in supply closets, kissing, me sticking my cock between her legs while standing up (her still dressed) and cumming that way, working my way to eating her pussy .
What opened the door to fucking her was me telling her how much she would enjoy it having her ass licked and massaged; the idea turned her on so much that within a day we were together in the company "archive room" that only her and a couple of people had a key, and she reluctantly stood against the wall while I raised her dress, pulled down her stocking & underwear, and proceeded to kiss her ass cheeks making my way to between her cheeks.
I told her that I needed to spread them, and with her stocking & underwear at her ankles she couldn't spread her legs, so I had her step out of them. She really didn't want to feel that exposed, but I knew what I was doing. after stepping out of them, I had her put lift one leg and put her foot on a box so she was completely exposed. I took my time, and gave her butthole a massage like I have done to many other women, but really took my time so she'd be horny as hell. It worked, because afterward she turned around, her pussy dripping wet, leaned against the wall breathing heavy, and just looked at me. She couldn't say it, but I knew she wanted me to fuck her right then, and I did with her leaning against the wall. I ate her pussy first, as I wanted to taste her and have her juices on my face when we kissed again. After licking her pussy and having my mouth rubbed all over it, I stood up, looked her in the eye, and held her left leg up as I slide inside her.
We kissed deeply, the taste of her own juices seemed to turn her on even more. She came really fast, and as I was close to cumming she made me pull out and shoot my load on the floor. That left me a little unsatisfied because I wanted to pump her full, something she did NOT want to happen.
She told me awhile back that she couldn't get pregnant, but that cumming inside might be too much for her.
Yeah, right, so I made a plan. over the next couple of days when we talked on the phone, I kept saying how much I wanted to massage her ass with my tongue knowing this would drive her crazy, and sure enough within a couple of days of our first experience, we planned to do it again in the late afternoon with all the executives were gone (like we always did).
It went the same way - she was in the room first, i entered, she looked at me and leaned against the wall, but this time after removing her stocking and underwear, I said her skirt was kind of "in the way" so I slid it off of her. she didn't protest because I knew she wanted that butthole licked again. after having her step out of her skirt, she was now totally naked from the waist down. I took my time on her butthole, and continued giving her a butt fucking with my tongue.
She was almost in another world, her body slowly moving with my tongue, so I reached up and began pulled her sweater up. she didn't protest at first, but when she realized it was about to go over her head she said "please no".
I wasn't stopping now, and said "i'm going to lick every part of your body like I've licked your butt. She let out a long breath, and seemed to relax so I stood up and pulled her sweater over her head and off.
She was now leaning face first against the wall wearing only a bra, and that had to go, so I unhooked her bra, had her pull out of it, and now she was 100 % naked in this room. I went back to tonguing her butthole for a few minutes, then had her lay on the floor ( it was carpet) and started at her toes, licking and kissing my way up to her pussy, though I passed it and went to her tits.
I slowly but deeply sucked her right nipple first, and quickly realized it was producing juice. (long after this she told her tits continued to produce juice after her son was born, but her husband didn't like that and stayed away from them).
I worked her tit milking it and drinking all it would give until it felt like nothing else was coming out. I then went to her other breast and it was producing as well, so I milked it long and deep. She was in another world, her hips raising her because she was so horny from me doing this.
She couldn't take me doing this and slid a finger into her pussy. I realized after she started, and I stopped and took her hand, removed it from her pussy and licked each finger.
She was in so much pain, she whispered "please do it" and I did. I entered her on the floor, but over the next 30 minutes I fucked her in every position and many she had never done. She came so had once that she blacked out for a few seconds, but I never slowed down. We finished with her back against the wall, me holding her in the air by holding her up under each leg, her arms around my neck, and me fucking like a jack hammer. When I started to cum, there was no way I was stopping to pull out so I pounded her while cumming. She got emotional, and once I finished cumming I eased us both to the floor.
She had a few tears as it was a barrier she never thought she'd cross, but it was done, and now she knew I owned her.
We had many more encounters, and even led to anal sex, but that's a story for another time.
