This is a continuation of my first posting, "Practice Date."
While it is not necessary to read "Practice Date" first, I recommend you do. It will help with the character development.
Additionally, to those of you who left feedback, thank you very much, I was flattered.
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While Saturday morning is the time I do yard work for Mrs. Webster, Friday afternoon is the time I try to do likewise around home. I attend a local college and don't have the money for my own place, so I volunteer to do most of the dirty work around the house. I want my parents to think they should keep feeding me.
I had just put the last of the lawn tools away and was heading inside for a cool drink and a warm shower when the phone started to ring.
"Hello."
"Oh, good, it's you. I was hoping you would answer." It was Mrs. Webster.
"Hi. How are you?"
"Hot for you, but that's not my immediate reason for calling. Do you have a minute, I want to ask a favor of you?"
"Sure, whatever you want." I was pretty sure she knew I would do anything she asked.
"If you have nothing planed for tonight, would you be so kind as to join me for what may turn out to be some new territory?"
I immediately remembered her comment of last Saturday when she alluded to "new territory" as maybe being her shapely ass. My cock twitched.
"I'm all yours. Tell me what you want me to do."
"I want you to be at my place at 9:00, tonight. Something like what you wore last week will be fine, and be sure to bring a pair of swimming trunks, baggies like last week, too. There is someone I want you to meet. See you tonight." The line went dead and I returned the earpiece to its cradle. Almost immediately the phone rang again.
"Hello."
"I forgot to tell you, no jacking off before you arrive. Bye." Click.
I looked at my watch, 6:30. Only two and one half-hours of not jacking off, I wondered if I could make it.
I did make it, and I knocked on Mrs. Webster's door ant exactly 9:00 PM.
She opened the door within moments, reached out with her hand and pulled me inside and embraced me, pushing her great tits into my chest and kissing me full on the mouth.
"I've missed you, Bobby. My pussy's missed you, too."
"I am truly thankful for that," I responded, my lips barely touching hers.
"Now, what are you here for? I know you want to know. All I can tell you is that a teacher friend of mine is here, and I thought she might like to meet you. I've told her we have a more than casual friendship, but no other details. If the two of you get along, well, we'll see. Now let me introduce you to her. She's, out by the pool."
When we got to the pool, Paula made the introductions, "Helen, this is my very good friend, Bob. Bob, this is my very good friend Helen, we teach at the same school."
"Helen, I am very happy to meet you. Paula has told me absolutely nothing about you."
"Wise ass," muttered Paula, and Helen smiled.
Now, let me tell you, Paula was a babe, I knew that both from close observation during the years I had been doing yard work for her, and from some very close personal contact last Saturday evening. At first glance, Helen was just as attractive. She had light brown hair, a beautiful face and even sitting in the patio chair it was easy to tell she had a real nice figure. She was obviously older than Paula, but how much I really couldn't say.
"There are chips and dip on the table, sodas too, if you want anything. We were waiting for you and then we thought we would have a little swim. What do you say?"
"Great. I'll change into my suit and be right out."
When I returned to the pool, both Paula and Helen were in the water, their shorts and blouses folded over the backs of their chairs. They were sitting on the middle step and the water came to their waists. Two beautiful women, four large boobs, and the promise of two fine asses awaited me. I took three quick steps and dove into the deep end. It was the only way I could conceal my rapidly growing cock.
We talked, laughed, told jokes and generally kidded around for about 15 minutes during which time the women only got wet to their shoulders, being careful to keep their hair dry.
I was wondering about that, when Paula said to Helen, "So, what do you think, do you want to move on to phase two?"
"I'm really nervous, but Bob does seem like a nice young man, just as you said. And, I am determined to move on to sometime, so it might as well be phase two."
Paula said to Helen, "Great, I am delighted for you. I'm sure you won't regret your decision."
Then to both of us, "Let's dry off a little, and I'll give Bob the background and then tell you both what I have in mind for the rest of the evening."
With large beach towels wrapped around us, and seated at the backyard picnic table, Paula presented her plans for the evening.
"Bob, I told Helen about last Saturday evening. Not in any great detail, but enough."
My eyes went straight to Helen's and I am sure she was blushing as much as I was.
Paula continued, "Helen was divorced five years ago, and has not had so much as a date since then. If that were not bad enough, she was raised in a very religious family and married a very religious, unimaginative man. For them, sex was only for babies, not for fun or pleasure. She and I have talked about this in great detail over the past few months and she wants to, how should I say this, expand her horizons. After our relationship changed last week, I presented her with the idea of the three of us getting together and she agreed to meet you. Now that she has meet you, she has agreed to move forward with her, let's call it, education. Helen, do you have anything you want to add?"
"Oh, Lord, I am so nervous and embarrassed," her voice was almost a whisper. "But I am resolved, and I trust Paula, and, Bob, I want you to promise you will never tell anyone about this, do you promise?"
"Yes, I do. Actually, Paula and I never talked about it, but I have no intentions of talking about us, either."
Paula interjected, "I never doubted you for an instant, but thank you."
"OK," continued Helen, "All this is so new to me, I can't even begin to tell you how scared I am. All my life I have been told sex was dirty and men were evil, and don't let them touch you except for your "wifely" duty and all kinds of crap like that. Can I say crap?"
Paula and I nodded.
"Now, here I am at the ripe old age of 43 and I see my life going down the toilet and I want to have some fun but I don't know how. Don't get me wrong, I've had men ask me out, but they are older, and undoubtedly experienced and that terrifies me. What am I to do, act frigid and refuse intimacy, or accept their advances and then not know what to do, other then lay on my back and spread my legs? I'm sure any man, other than that "ex" of mine, would expect a woman to do something, and I would be too afraid, worrying that I might make a fool of myself. It's humiliating! I want it to end! So there."
Paula looked at me and asked, "Are you all right with this?"
I nodded and said, "Yes, yes I am. I know how she feels, or at least a little bit about how she feels and, well, yes." I really couldn't think of anything else to say.
"All right," exclaimed Paula. "Now you two can stay here and chat for a few minutes, I have to do a little creative writing. Now while you're talking, don't forget that you two are going to have sex together tonight. " And with a huge grin on her face, she left me alone with Helen.
Talk about your pregnant silence. Finally Helen said, "She sure has a way about her, doesn't she?"
"A way I really like," I said. "Do you know what is going to happen next?"
"No, all we agreed to was that if I liked you, and if I then wanted to try some new things, she would take the lead and I would only have to do what I was told. She said it would be easier that way, and so far she is right about that."
"I have a policy of complete honesty with Paula. I decided last week that if she was going to share herself with me, she deserved to know my real feelings and emotions. We agreed to total honesty between us. I want to have the same starting point with you, do you mind?
"No I don't mind. I think it's great and I think all the more of you for putting your cards on the table, as they say."
"Then let me say that I think you are a really beautiful woman. When Paula called this afternoon and said she wanted me to meet a friend of hers and my mind immediately started going a million miles an hour. I had all kinds of fantasies. Would you be young, old, good looking, ugly, nice, mean, you know, all of that. Now that I know you a little, I just want to say I think you are as nice as you are attractive, and I think you are really, really, good looking. My cock's been hard almost every minute since I got here."
"Wow, I like your honesty. I would not have believed I could be attractive to such a good-looking young man as you. I think I am going to have a much better time tonight than I originally thought. Thank you."
'OK you two, I'm ready. Bob, you can shower in the guest bath. I laid out what I think you didn't bring. When you're ready, we'll see you in the living room. Helen, you and I will change in my room."
"Change? Change into what? All I have is my shorts and blouse. I wore the swim suit under them."
"No, you have some other things here, too. I went shopping for you on the way home this afternoon. I knew that after you met Bob you would want to continue. You'll love the items I picked out for you. Come on, where're wasting time."
I cleaned up quickly and was waiting in the living room when I heard Helen shriek from the bedroom, "You don't expect me to wear that, do you?