Practice Date

by Chicago Bob


I awoke early this Saturday morning, just like I did every other morning. Not having an active social life left plenty of time for "early to bed, early to rise." Don’t get me wrong, I very much wanted an active social life, but I was shy. To tell the truth, I was painfully shy at times, especially those times when meeting or socializing with girls was on the agenda. Don't get me wrong, I wasn't a virgin, I had had some experiences with girls, but to this day I suspect that the two girls who did it with me were more motivated by sympathy than true feelings of romance, or even lust for that matter. Let me tell you, being the object of a sympathy fuck did nothing for my self-esteem or my shyness.

Anyway, it was Saturday and Saturday morning was when I worked for Mrs. Webster. I liked Saturday mornings. No more bicycle rides to her house, however, I was now a college boy with a great '56 Chevy, two door hardtop. I had saved every dime I could through high school to buy a great looking car. I thought it would change my luck with the girls but I spent more time alone in it than I ever imagined. Still, it was better than the bike.

I arrived at Mrs. Webster's house at 9:00 AM, just like every other Saturday, and just like almost every Saturday, she was already at work in the flowerbeds. I called a "Hi" to her and went to the garage and rolled out the mower and trimmer. As usual, we worked mostly at our different jobs without too much conversation other than the usual banter about the weather, it was going to be a hot day, and how nice it was to be out of school for the summer. This was true for both of us. She taught sixth grade at an elementary school across town.

After doing the front and back yard lawns, raking the grass cuttings and leaves from around the backyard trees, cleaning the pool, sweeping the sidewalk, and returning the equipment to the garage we stood side by side and agreed that, together, we had done a great job. And we had, in fact. The yard looked wonderful. Actually, I thought it was Mrs. Webster who looked wonderful. Even covered with sweat and dirt, she seemed to glow. Then she did something she had never done before, she invited me to stay for lunch.

"Tell me Bob, if you don't have anything else to do right now, would you like to stay for lunch?"

"That would be great," I said, "I don't have anywhere else I need to be today." My friends could surf without me this afternoon and I would be happier taking covert looks at Mrs. Webster than at the girls at the beach.

"Great," she replied. "I am going to take a quick shower, and then while I fix a couple of sandwiches, you can take one too, if you would like to that is?

"Sure, a shower is definitely called for right now, and I have an extra pair of swimming trunks in the car. I can switch into those after I clean up."

"OK, you know your way around. Make yourself at home while I get this dirt off of me. If you want to, we can eat by the pool and maybe take a swim."

Well, I wanted to do anything she suggested so I agreed to a poolside lunch and was delighted to be staying for more than just the yard work.

Showers over, sandwiches eaten, glasses of iced tea refreshed, we sat comfortably at her back yard table. Throughout lunch we had talked of school, both hers and mine, plans for the summer, my career path, the health of my family, and the prospects of a bigger US involvement in Southeast Asia. Throughout it all, I had been very gentlemanly and avoided directly staring at her. This took a superhuman effort on my part because she was wearing a pair of white, very short, shorts and a white tee shirt that maddeningly suggested she might not be wearing a bra. For my part I was just grateful that the table at which we sat did not have a glass top and that my swimming suite was the baggy surfer type that was in style those days.
Then came the second surprise.

"So, how's your love life, Bob?"

I kind of gasped and then felt myself blush what I was sure was a crimson red. This was territory into which we had never ventured. For all of the three plus years I had been working for Mrs. Webster we had chatted about a lot of things, but never anything this personal. I didn't know how to answer and just looked at her.

"Did I embarrass you," she asked. "I know it's a rather personal question, but after a year in college, especially that party school you're going to, I would think such a question would be welcomed. You know, give you a chance to brag a little. So, tell me, how's your love life?"I quickly reviewed the three years of conversations I had had with Mrs. Webster and realized I knew very little about her, other than she was divorced. I knew nothing about her ex, the reason for her divorce, nothing about her past or present social life, really nothing personal about her at all. Yes, she had made comments about some plays and movies so I assumed she was at least dating, but how often and with whom I had no idea. Really, her personal life was a mystery to me. And now this question from right out of left field. Left field maybe, but asked as a simple, matter of fact question. I decided I would tell her the truth. "Truth, justice, and the American way," that's my motto.

I looked her right in the eye and said, "I have no love life."

"Really? You are a good looking, intelligent young man, I would think the girls would be swarming around you like bees to honey. I for one can say I have certainly enjoyed your company all the times you have been here to do the yard. Actually, as you have grown older, I have grown to look forward to our Saturday mornings."

"Well, thank you. I appreciate your saying that, I really do, but to tell the truth, I have a real tough time with girls. I get really nervous when I am around girls. Being with just one girl is even worse. I say stupid things, or do something really ridiculous. I end up being so embarrassed I have stopped trying."

"You don't seem to have trouble with me. You seem relaxed and at ease and I can't recall your either saying or doing anything stupid or ridiculous."

"No, but you are not a potential date. And, you are at least twice my age, well maybe not twice, but there is no chance of us going out together, so I don't feel nervous around you."

"Thanks for backing off on the twice your age comment. Just for a moment you made me think of myself as a dinosaur. OK, I won't push. Help me clear the table and I will set you free to enjoy the rest of the day."

"Mrs. Webster, you are the most beautiful woman I know. I sure don't think of you as a dinosaur." And it was said. Why I said it I had no idea, but it was out there now, and I felt another bout of crimson rush onto my face.

With a big grin she said, "Thank you Robert, you just eliminated the dinosaur feeling." And with that she picked up our plates and took them into the kitchen. I followed with the glasses and napkins.

After putting the plates on the counter she turned and looked at me. "Have you always been so shy? You've told me about some of your dates in high school. What is it, the college girls intimidate you?

"It's not the college girls, it's all girls. I've always been shy. The dates in high school, and both of my dates in college, were only because the girls asked me, and then only the one time. A social butterfly, I am not."

As I said this, she leaned back against the counter and crossed her arms. The effect was to accent her breasts and even with her arms crossed there was still some tension in the tee shirt material that was stretched between them. Her nipples were clearly outlined beneath the white fabric. I couldn't help but look and she couldn't help but notice my looking.

Without thinking I said, "Please don't do that."


"Cross your arms like that, it makes it difficult for me to maintain eye contact."

She smiled and let her arms drop to her side. I thought the outline of her nipples was just a little more prominent, but I quickly looked directly into her eyes. Neither of us spoke for what seemed like an eternity.

Finally she said, "You're right, that was unfair of me. I'm sorry. I know I have a nice body, and I know you have noticed it many times over the years. I want to thank you for being such a gentleman about it. That's why you have kept this job all this time. Believe me, there were others before you who couldn't keep their eyes in their heads. It can become very distracting, even insulting at times."

"It's been difficult. Especially those times when you wore a bikini while you worked. Those Saturdays were both the worst and the best times I had working for you."

She laughed and said, "How about this? You said you have no commitments today, so why don't you come back for dinner, say 8:00 PM. I think of you as a friend, and I would like to help you feel more comfortable around girls, women. We can call it a practice date, or am I being too bold, again?"

I was dumb-struck. I just looked at her. My brain was reeling. I blushed again, big time.

"I'll take that for a yes. Now, off you go. I have some things I want to get and you should go to the beach. You need to cool off. See you at eight." With that she pointed to the door, and I left.

Eight o'clock. That was seven hours from now. Time enough to do a lot of surfing and time enough to do a lot of thinking. What could she have in mind? She said she liked me, but that was such a benign comment I didn't feel I could read anything into it. Hell, I couldn't read anything into anything. I had mowed this woman's lawn and raked her leaves for three plus years. She was a nice lady and she was just being nice to me, a shy kid who found it extremely difficult being around girls. She was just trying to give me some practice being with a female type person hoping it would help to lower my anxiety about dating. I decided Mrs. Webster was just being kind. Don't read anything into it.

So, I spent the afternoon surfing and failing completely in my attempt to not read anything into it.

Around 7:00 PM I showered, very sparingly applied some cologne, and dressed in a pair of tan slacks and a light blue cotton shirt with a button- down collar. Brown penny loafers completed the ensemble.

As I was leaving, my mother and father gave each other a questioning look and my father asked, "Have a date, son?"

"Not really, just going out with some of the guys."

"Well, have a good time," said my mom, and I was out the door.

There must have been a party in the neighborhood because Mrs. Webster's street was full of cars. I had to park over a block away. At exactly 8:00 PM I knocked on her door. What greeted me took my breath away.
Mrs. Webster was wearing a black cocktail dress, cut low in the front. There was a lot of cleavage.

"Hello, right on time," she said not missing a beat in response to what must have been a look of unbridled lust on my face. "Come on in. I don't see your car, did you drive over?"

"Yes," I said, managing to keep my voice calm. "I had to park down the block. I think someone is having a party."

"Oh, that's good," she said.

I didn't really understand what she meant. Good for the party or good for the parking down the block. Remember, Bob, don't read anything into anything.

But I became a speed-reader when she turned to go into the living room. The back of her dress was missing. She was bare to the waist. That meant the cleavage was real. No foundation garments, as they say. But there was more, her great legs were encased in black stocking with high heeled pumps, and she was wearing her long blond hair up, revealing her very sexy neck. My cock started to rise. I started to panic.

"Now, don't get excited," she said, not knowing how prophetic her statement was, "I just wanted to dress up a little to help compensate for the age difference. I thought looking like this would make this "date" more like a real one, at least as far as you being under pressure, and you would have to focus more on yourself than if it were just me, even me in a bikini."

"Wow, you look wonderful," I stammered. "For some reason that dress seems a thousand times more sexy than any bikini ever could. You look great!"

"Why thank you sir, now have a seat while I get some hors d'oeuvres." And with that, she left the room.

None too soon for me. I quickly took a seat at one end of the sofa and adjusted my rising cock to help conceal it in my slacks. I was thinking I should have worn something less revealing when Mrs. Webster returned with a plate of chips and a variety of dips. She leaned over in front of me, offering both the chips and an excellent view down the front of her dress.

Looking me right in the eye she asked, "Is this unfair of me, too?"

Rising to the occasion, in more ways than one, I said, "Yes, but I really like the view." I was surprised by my boldness.

Standing up she simply said, "Thank you." Then she put the plate on the coffee table and sat beside me. "I think you handled that rather well. Or more accurately, you responded rather well. I must be good for your shyness."

"Mrs. Webster, I have to be honest. I have never been more nervous in my life. I just decided that tonight, when you answered the door, I would be as honest as I possibly could, no matter what. I have the feeling I will learn a lot more on this practice date if I'm completely honest with you."

"Good for you. Honesty in a relationship is always the best recipe for success, and if being honest kills the relationship before is begins, all the better. That way you will have saved all that time waiting to discover all that's wrong with being together. Now, I think that after letting you look down my dress, you can call me Paula and not Mrs. Webster. What do you say?"

"OK, Paula it is. Actually, I have been thinking of you as Paula for a long time, so I don't think I will have much trouble calling you Paula to your face."

"Oh, you have been thinking of me as Paula, but calling me Mrs. Webster to my face. When, exactly, have you been thinking of me as Paula? And remember, you said you are going to be honest."

I knew where she was going with this although I couldn't believe she was pursuing it so strongly. This was not the same lady I had worked for all these years. More accurately, this was a side of the lady I had worked for all these years that had been kept hidden from me. I thought I might get to like this side of her.

"I think of you as Paula…when I masturbate."

"I know," she said, and then, "let's eat."

During dinner, lasagna with bread sticks and a green salad, we discussed our personal lives. I told her about my uneventful love life, including what I categorized as my two sympathy fucks. She told me about her ex-husband and the reason for her divorce. She said he was verbally abusive and she decided to get out of the marriage before he started getting physically abusive. She also told me that she dated from time to time, but that being a teacher put limits on her social activities and she was uncomfortable trolling, that's the word she used, for men in bars or clubs. As a result, she had had only two longer-term relationships in the four years since her divorce.

I asked her how her husband had taken the divorce. She was, after all, a very attractive and desirable woman and I thought any guy would be upset at loosing such a great looking wife. This is when she told me she could not have children, something to do with the quality of her eggs, and that he was almost happy to be out of the marriage. He wanted kids but she couldn't produce. End of story. End of marriage.

By this time dinner was over, we had cleared the dishes, twice in one day, and we were back on the sofa, sitting very close together.

"What now?"

"That depends on you," she said. "What do you want to do?"

"I want to kiss you."

"OK, stand up. I think kissing is best done either standing or lying, but not sitting side by side."

As I was standing I said, "Aren’t you being kind of cold blooded about all this."

"Sit back down," she said, "and I will explain how I feel about this evening. You deserve honesty just as much as I do."

I sat on the couch and she sat on the corner of the coffee table, crossing her legs and revealing a lot of nylon clad leg. I swallowed hard.

"Bob, I am very much aware of the difference in our ages. I am also very much aware of the difference in our lives and in our circumstances. For three years you have come to my home almost every Saturday to mow my lawn and trim my trees. For three years I have watched you mature into a really good looking young man, and for the last year I have thought about you the same way you have thought about me. I think of you when I masturbate."

She must have seen the shock on my face. A woman masturbating was something I had never thought of, although now, after she said it, it seemed logical enough.

"Yes, women masturbate just like men. Well, not just like men, the equipment is different, but we do enjoy the feelings of pleasure masturbation provides. As for me, I have learned that a pragmatic attitude towards sex is a good thing. Sex is sex, love is love, and sometimes the two intermingle and other times the two are mutually exclusive. Tonight, with you, sex is sex, with me, if you want it."

I had hoped for this but never believed it would ever happen. Even after the crossed arms and the appetizer view I thought she was only playing with me. Now here she was, the woman of my dreams, telling me she would have sex with me, if I wanted it. Of course I wanted it.

All I could do was nod. Finally, "Yes, I would like very much to make love with you."

"No, not make love, have sex. There is a difference. With you it's sex not love. Don't confuse the terms or the feelings. Although at your age we could maybe compromise a little and say 'make lust.' So, let's make lust. Do you want to lead, or would you like me to set the pace. I have to tell you, if you let me set the pace you may get frustrated after awhile."

For this angel I would do anything, and if she wanted to set the pace I was willing to go along. "OK, you set the pace."

"Thank you, we'll both have a better time. Let's go into the den. There's no carpet on the floor and we can dance a little."

She must have been confident of her plan because it looked like she had the music ready to go. Once in the den she turned on the hi-fi and Glen Miller's "String of Pearls" came from the speaker.

She turned, smiled, and came up close to me, putting both arms around my neck. I in turn held her by the waist and we met in a full body hug.

"Now, let's have that kiss," she whispered.

Our lips met for the first time and I was in heaven. Then heaven got even better as I felt her tongue brushing against my lips. Parting them, she delicately played her tongue over my lips and then inserted it into my mouth. I knew about this, it was called French kissing, and I liked it. Soon we were in a loving battle of tongues. All the while I could feel the heat of her body as she held it against me. Her breasts felt wonderful as they pressed against my chest. My hands instinctively left her waist and dropped to her tight little butt. Yes, I was in heaven.

"That was nice," she sighed as our lips parted. "I notice you are glad to see me because I know that's not a pistol in your pocket."

Embolden, I pushed my now completely erect penis against her. She in turn leaned back and actually ground her pelvis into me. It was great.

"Do you think you can last? I know at your age even a little excitement can produce serious results."

"So far so good," I more exhaled than spoke.

"Well, let’s not push it too far. I want you involved for the night and I don’t think you will be able to keep your mind on me as much as I want if you are always on the brink of ejaculation. Follow me."

With that she pulled away from me and walked toward her bedroom. On the way to the bedroom she grabbed a towel from a hallway closet and then spread it on the floor in front of the full-length mirror on her closet door. I had no idea what she had in mind, but whatever it was I wanted to be part of it. Following her into the bedroom, looking at that lovely back, the stocking covered legs, the heels…I knew I would do anything she wanted.

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