Part-time Work With Benefits
I've mentioned here more in more than a few posts of my experiences with older women. For the most part, my lovers have been attractive women who would have no trouble in getting attention from men, and I was fortunate in that these women were receptive to having a younger man as a lover, with no expectations, except in one case, other than to have fun.
A former boss was an exception to this 'rule.' 'Toni' was about 5'2', on the heavy side, curly hair that always seemed to be unruly, glasses, but always dressed professionally, though she never wore dresses, as she felt her legs weren't her best feature. She did have a pleasant face, a friendly smile, and lips that I found myself wondering one day would feel like to kiss.
I had been working for her part-time in a bookstore for over a year. Since we were relatively close in age, we became friends of a sort. She told me of her divorce, as I did of mine, and the problems we had in dating. I didn't tell her that I had been enjoying sex on an irregular basis with various older women, and really hadn't thought about a relationship, having too much fun making up for lost time.
I had been helping her in the back room to unpack new books and load them onto carts. This continued during the evening, and after the store closed, she went into the backroom to tally up the day's totals, while I continued to work. It was warm in the room, and I had removed my shirt and my t-shirt was showing signs of sweat. Toni had taken off her red blazer, and her white blouse was a little damp as well. I heard the phone ring.
'Oh, hi! Just closing up. What? Oh. Oh. Well, that's okay, Phil. I understand. Damn. Next week? I'll let you know. Bye.' Then, the sound of the handset slammed into the receiver.
I went into the office. Toni was sitting there, tapping the phone, looking very unhappy.
'X, that sonofabitch Phil said he his wife was going to be out of town tonight and tomorrow, but then he calls tonight at the last minute and says that she decided to stay home. 'Stay home', my ass! He thinks that just because I'm single, that I'm going to wait around for his call and fuck him when he wants! Well, he can just wait until I decide he's going to get a piece of ass!' I had never heard her talk like this before. I told her how sorry I was, and that dating married people was a pain in the ass sometimes, remembering how often I was geared up for sex with a married lover, then getting a phone call that the date was off that day or night.
I patted her shoulder, and she reached up and patted my hand.
'You're a good friend, X.' Then Toni took my hand and kissed it!
I took her hand and kissed it. I pulled on her chair, and it rolled back from the desk.
'I want to give you a hug, Toni.' She got up, and I put my arms around her. She did the same. She felt softer than many of the women I hugged, but smelled very nice, and a little sweaty. I squeezed a little, and she returned the gesture. I made a little joke that she was too sweaty to go out anyway, and she laughed. I squeezed her again, and again she reciprocated. She kissed my cheek, and I hers. She pulled back for a second, looked at me, and then kissed me on the lips, lightly. I was fast enough to kiss her back. She pulled back again, and then moved in to kiss me once more, this time pushing in her tongue.
'Okay,' I thought, 'I'm going to get fucked tonight.' Toni wasn't my first choice, but she was here, my cock was up, and it had been awhile since I had been laid.
I kissed her back, putting my hand behind her head, pulling her close while I took time exploring her mouth with my tongue. She moaned into my mouth, squirmed, and tried to pull back. I held her head firmly and continued kissing her. She whimpered, and I felt her arms tighten around me. When I broke the kiss, she was a little sweaty, a strand of her in her face, her lipstick smeared.
'Oh, shit! No one has ever kissed me like that! Especially a very sexy younger man! Do it again!' I did so, moving my hand to her blouse, and stroking the tip of her bra, feeling a hard nipple. She groaned and squirmed and moved her hand to my ass.
When we stopped kissing, she said, 'I've always liked your cute little butt, X. Please take off your t-shirt.' She sounded hoarse. I did.
'Oh, damn. What a nice body.' She moved in to kiss my chest, and then started sucking one of my nipples. It was my turn to moan, and I told her I loved having my nipples played with.
'You do, honey? How about having your prick played with?' I kicked off my shoes, dropped my pants and underwear, and stood naked before Toni.
'Oh, shit! I want that cock in me, but first, I want to do something I've fantasized about for awhile. Sit on the desk, X.' I did, facing her.
Toni sat down in her chair. She moved so I was directly in front of her. She reached up, wrapped a hand around my penis, and began stroking me.
'Oh, X. You have such a wonderful cock. Come, X, come for me. Come on my face!' She stroked me faster. I came hard, spraying semen on her cheek and lips. She licked her lips.
'Oh, goddamn, you taste good, X! I'm going to enjoy sucking you dry.' She stood up, unbuttoned her blouse, took off her pants, and her panties, and as we kissed, I rubbed and fingered Toni. She came quickly, and we spent the rest of the night in her office, fucking and sucking each other. You'd never know it to look at her, but she gave me some of the best handjobs I've had in my life, knowing how to get me right to the edge, then back again, before letting me come. We stayed lovers for about 2 months or so, and she said she enjoyed how she was cheating on her lover, especially with a younger guy.