Sally's Sr. Sex - Darren

I was having lunch with my group of retired teachers; we meet at a different place each month. This was my first visit to this little grill. The menu was varied and there seemed to be something for everyone. I was wearing a blouse with a loose neckline today and even though I didn't let on, I noticed that the shy waiter was looking down my top at my breasts as he stood just to my left to take our orders. Later, I observed that throughout our meal, he seemed to be looking at me regularly and we often made eye contact.

He was nice enough looking and was about 6'2" tall with had really big hands. I wrote a note on a small piece of paper and wrapped my tip around it and I handed it to him directly rather than leaving it on the table as the other ladies seemed to be doing.

My note simply said, "Call me." My name, Sally, and my phone number.

I had nearly forgotten about the whole incident when the phone rang about 9 AM three days later. "This is Darren from the grill. Your note said to call you. Did I do something wrong?"

"No, you did nothing wrong, you just seemed like you might need someone to talk to and I want to offer my services."

"Oh, that would be great. I just recently moved here and I know no one. You reminded me of my mother's sister and made me realize how alone I am here. I called because today is my day off. I didn't call earlier because I didn't want to disturb you in the evening and I normally work all day."

"Let me take you to lunch. I know of a little place on the beach that serves great hot dogs and fries. Do you have transportation or would you like me to pick you up?"

"I have a bike, but I am used to going most anywhere on it."

"Give directions, I'll come get you."

Darren was renting the furnished, converted single car garage of a house near where he worked. When I got there he invited me in for a look. The furnishings were Spartan, but Darren kept everything picked up and the place was clean. It was a studio apartment with a small kitchen, complete with a table and two chairs, and an enclosed bathroom at one end; his bed, which converted into a couch, a chair and a TV at the other.

Darren told me his life story over our more than 3 hour lunch. He was 18, had graduated from high school in May, and was planning to work and attend the local Jr. College. He knew no one here and had never had a girlfriend. He wanted to, but was too shy to approach girls his own age. We held hands while we talked, or rather, while he talked and I made encouraging noises. Darren seemed to be very comfortable with me for some reason.

I told him that I had seen him looking down my blouse at his grill and he told me he was fascinated by breasts and had only seen them in pictures and on the internet. I told him we would see what we could do about his education - and left it at that.

The grill where he works is closed on Mondays, so I invited him to our house next Monday so he could meet tgg.

Tgg told me that it sounded like I had taken on a project, but said, yes, bring him over.

When Monday rolled around, tgg was in rare form. Over tuna fish sandwiches and chips, he told Darren about his inability in the bedroom since his prostate cancer and that if Darren wanted to get it on with me it was okay with him. Darren is a virgin, and was so embarrassed that I thought his ears might fall off. He had not expected to hear anything like that. Tgg excused himself, he seemed not to notice Darren's reaction, and said he was going to the plant nursery and would be home by dinner time.

I didn't call any attention to Darren's embarrassment either and just talked casually with him as I cleared the table. He helped wash the luncheon dishes and naturally my T-shirt got wet in the process, causing my bra-less breasts to be more exposed than they had been when my T-shirt was dry.

It was a hot afternoon. We were sitting by the pool talking when I ask Darren if he would like to cool off with a swim. He said a swim would be great, but he didn't have a swim suit. I told him we didn't use swim suits in this pool, stood up, kicked off my shoes, dropped my shorts, pulled off my top and jumped into the pool. Just like that!

When I was in chest deep water, I stood up. My breasts were floating at the surface and I said, "Darren, come on in, the water feels good."

Darren turned his back, slipped out of his shoes, pulled off his shirt and dropped his shorts and boxers. He crossed his hands across his privates and jumped into the pool. His hands did not totally cover his equipment and I got an eyeful as he raised his hands when jumped in.

I asked Darren why he was so shy about showing his cock and his answer surprised me. All through high school, whenever he had to change for PE in the locker room, or whenever the other boys saw his penis, they would tease him about being too big, about never being able to get a girl because no one would be able to handle him, etc. It got to the point where he would fake being sick just to avoid PE and didn't go out for sports, even though he was a really good basketball player and runner, for the same reason.

I walked over to Darren, reached under water and grasp his cock gently but firmly before he could pull away and told him that the boys were just jealous because they thought no girls would want them after seeing and feeling what he had hidden in his pants.

I told him that I could prove to him that he would fit into me anytime he wanted to try, but if he wanted to feel real breasts, this would be the perfect time while they were just floating in front of him.

Darren tentatively reached out and barely touched the top of my left breast with the pointer finger on his right hand. "You can really touch it; I'm not going to break." I let go of his, by now erect cock, and placed both of his hands on my breasts. Hand over hand I squeezed and manipulated my breasts and ran his hands all over them.

This could be interesting. It definitely felt good.

"Now let me show you the parts." I showed him my nipples and how they become erect like small acorns when he shows them attention, the same with my areolas. He was fascinated by the way they changed from wide and smooth to tight and crinkled. I explained how when a woman has a baby her breasts produce milk and I let him practice suckling. I told him how my breasts had changed over the years and led him to shallow water so he could see how they really hang down on my chest. I told him that every woman's breasts are individual to her - some large, some small. Some are soft while some are hard. Some are light while others are heavy and dense.

I explained that my body had changed over the years. I had been quite heavy only a year ago and because of my weight loss, I was not only healthier and had more stamina, but I also had hanging loose skin and wrinkles all over. We went to even shallower water and I had him feel my hard body under my loose skin. I told him that if he was turned off by what he saw, I would understand. I put my hand back on his cock and explained that men's cocks were like women's breasts in that each man's cock was different. Some are long and thick like his while others are short and thin and everything in between.

He asked about women being able to accommodate a cock like his and I responded that the cock goes into a woman where the baby comes out. If a woman's vagina can let a baby pass out, doesn't he think that a cock as large as a baby should be able to go in? I told him that I had experienced cocks of many sizes and shapes, but I had never seen a cock as big as a baby.

Darren asked if he could put it in me just to see how it felt to be inside a woman. I told him there was a lot more to it than just putting it in, but yes, let's go to the bedroom and take our lessons to the next level.

We held hands as we walked naked into the house and through to the bedroom. In the kitchen I picked up the jar of coconut oil as we passed through.

We reclined on the bed facing each other and, while stroking his erect cock, I explained that he should never put it in any girl unless she wanted him to. I ask him if he ever had wet dreams and if he knew what it was that came out of him. I explained that his emission was the man's part of making babies and unless he wanted to make a baby with his wife, he should know how the woman was protected from pregnancy and, to protect himself from the possibility of disease, he should use a condom unless he knew for sure that both he and the woman were both disease free.

I asked him if he was ready. I kissed his cock and then his lips. I reached into the coconut oil jar, filled my fingers with the thick oil and slathered it on his cock. I took another glob and placed it in my vagina. I lay on my back, spread my legs to open myself up and directed his rigid tool to my vaginal opening. I told him to go in a little bit and then pull back and do it again and again, going a little deeper with each push.

"Oh Sally, this feels so good."

"Darren, you are probably going to feel some really strong feelings in your cock and you will probably cum. When it happens, just let it go and shoot right into me. It's okay, I can't get pregnant."

Darren started pumping harder and faster and just as he was emptying his balls into me with a loud "AHHHHH," tgg opened the door and said. "Dinner is almost ready. Darren, you are welcome to spend the night if you want to." Darren's cock was still jerking in my vagina when tgg closed the door and went back to the kitchen.

"Oh Sally, can we do that again?"

"Let's take a quick shower and eat dinner. Tgg invited you to stay, so we have all night for you to learn more about sex."