This takes place several months after 'My Best Friend's Mom'.
I was missing 'Helen', primarily because of the great sex. As I drove down a street near her old home, I thought of how I had seduced her, and taught her more about sex than she had known before. As I became aroused, remembering the first time I taught her how to blow me, I drove by the church that was near her home and remembered 'Doris', the church lady, as I thought of her.
I recalled the first time I met her. I had to be measured for a confirmation robe. As I entered the office, I saw a woman in her late 30s at the desk. She had blonde hair piled on top of her head, with ringlets hanging down by her ears, blue eyes behind unattractive cat's eye glasses, and (as I recalled from a man's perspective) a nice rack, shown off in a tight sleeveless white dress that ended just below her knees, pantyhose, and matching white pumps. From what I could see of her legs, she had nice calves. She was also wearing pink lipstick, which I have always found very sexy, and makes me think of what it would be like to kiss the wearer.
Doris asked me what I needed, and I told her. She got up from her desk, told me to follow her, and I did, admiring her nice, firm ass swaying underneath the dress. When we got to a storeroom, she opened a door and took out a measuring tape. She kneeled down, and of course, my cock sprang up, seeing her dress hike up, showing off very firm, shapely thighs. To make me even more hard, she pressed the measuring tape along my inner thigh. I almost swooned; I was still very much a boy, and the slightest touch of a woman's hand always excited me. To have this woman, who looked very attractive to me, touch me in a way I wanted her to, was almost overwhelming.
Doris took her measurements, finally standing up. She had to have noticed my erect cock. She was so close that I was strongly tempted to kiss that mouth. She gave me a robe, told me to try it on, and when I fit, she told me to be sure to have it cleaned afterwards, and return it to the church. I looked forward to seeing her again, and in my adolescent fantasies about her, I had planned to ask her for a kiss. When I returned the robe, she wasn't there, so I left, feeling frustrated that my fantasy wouldn't come true.
Jumping ahead about 8 years, I went to that church with my then wife on a semi-regular basis. On one of those Sundays, as we were leaving, there was Doris. She looked older, of course, and a little heavier, but the tits were still there, and she was wearing a striped dress that ended below her knees, but the calves still looked good. That night, fucking my wife, I thought about Doris. I didn't see her again for another 5 years or so, after my time with Helen.
I pulled into the church parking lot, and went into the office. There was Doris, filing something, her back to me. She was wearing a blue dress that ended about mid knee, sheer black pantyhose, and blue heels that matched the dress. She looked pretty good. Her hair was pulled back into a bun, and tied with a black ribbon. She turned around, and I saw that she had traded in the cat's eye glasses for rimless ones, which looked very stylish. She had on pale lipstick. She still looked pretty good, even with a few lines around the eyes and mouth.
She asked if she could help me. What could I say, 'Doris, when I was a kid I used to jack off about you and wonder if you could jack me off now?' Of course, that wouldn't work, and would get me arrested.
As I introduced myself, the story I came up with seemed plausible as I told her. I told her that I was looking for information about the school the church had with the idea that maybe I might want to enroll my nephew there. She gave me the usual spiel, and asked me if I wanted to see the school. Of course, I said, and we walked from the office towards the classrooms. I figured that somewhere down the line I was going to have to figure out how to get her to go out with me, and try to get her into bed then.
She asked me how I knew about the school, and thought I had found my opening. I mentioned the confirmation robe and that I remembered her, and, truth to tell, developed a crush on her. She said, 'Oh, my!' and giggled. 'None of the young guys I've ever measured told me that before!' She laughed some more. Someone called out her name, and she touched my forearm, said 'Excuse me, X. I'll be right back.'
She concluded her business with her coworker, and returned to me.
'I'll show you the library we have, and that will pretty much be everything we have here.' She led the way, me admiring her ass and legs.
As we stopped by the library, she asked me 'Did you really have a crush on me?' I said I did, and she smiled. She told me about the library, how many books it had, and if I had any other questions.
'Yes, I do. I wonder if you would like to go to dinner with me tonight?' Her eyes got big, then she said she would.
'But aren't you bothered by the fact that I'm older than you?' I told her I was more comfortable in the company of more mature women. She thought that was unusual, but she still wanted to go to dinner with me. I said I would pick her up after she got off work. She said that was fine, as she could leave her car in the church lot with no trouble.
We went to dinner, and talked for several hours. She told me she had been divorced for some time, and that she wasn't quite ready to start dating again, and wasn't looking for something serious. That suited me just fine, as I was just looking for a new fuck, not a relationship.
As we walked to my car, in the now empty parking lot, I put my hand down by hers, and I felt her fingers intertwine with mine. We got to my car, and I turned towards Doris.
'Are you sure you want to get involved with a woman who's about twice your age?' I pulled her to me and kissed that mouth. It was as sweet as my fantasies. Her hands rested on my hips.
When we broke the kiss, she said that we should get inside if we were going to do any more necking. I opened the door for her, seeing her draw her shapely legs inside.
When I got inside, she leaned over, said 'Hi' and kissed me, hard. Surprising me further, her hand slid onto my thigh, one of the things I wanted her to do in my youthful fantasies. Of course, I put my hand on one of those legs I wanted to touch for so long, and enjoyed the feel of the nylon, and the muscle of her thigh.
When we came up for air, one strand of her hair was hanging down by her ear, reminding me of the ringlets she once wore. I told her about how the feel of her hand on my thigh when she had measured me for a confirmation robe, and my erection.
'I always enjoyed doing that', she said, shocking me. 'Young guys are always ready to have a hard-on, and it doesn't take much to trigger one. I always volunteered for that job, so I could see how much young cock I could excite. Afterwards, when I got home, I would either be so horny that I would fuck my husband's brains out, or jill off when he couldn't fuck me.' She kissed me again, her hand moving over my cock.
'I never would have made a move on any of you guys, since it was illegal, and wrong, and besides, you wouldn't have lasted very long, and I wouldn't have gotten any satisfaction, but it was fun thinking about how hard I could make you guys, and fantasizing about teaching you about sex.' I asked her if she had fantasized about me, and she said she probably did, but had forgotten me, as she had the dozens of other boys she had measured.
'But you're here now, you're hard for me, and there's no reason why I can't jack you off, take you home, and spend the night fucking and sucking you.' She kissed me again, her tongue filling my mouth completely, and I felt her fingers unzipping me and taking me out. She broke the kiss for a minute.
'Here's your reward, sweetheart, for being confirmed.' She kissed me again, as passionately as she could and started jerking me off. I came within seconds. After I regained my composure, she told me to take her to her car, and follow her home. She said she wanted me to leave my cock hanging out, and think about how much I had wanted her back then.
'I want to look at your prick become stiff about me. I'll give you the best loving you've had in a long time, I promise.' She did, and we were lovers for nearly 4 months, when she decided that maybe it was time to end our fun, since it was just that, and not a commitment.
Oh, yes, I almost forgot. During some of our sessions, we reenacted her measuring me for a robe, except she was wearing a short white skirt, no bra under her blouse, and she masturbated me through my 'robe' (really my underwear), and wore the pink lipstick when I told her about it, and kissed me when she was finished 'taking measurements', making sure I could taste the lipstick after each kiss. Fantasy is fun, but the real thing is even better.