Riding With Grandpa

by Tony Tiger

Copyright© 2019 by Tony Tiger

Erotica Sex Story: A couple of sex surrogate interns change a young boy's idea of love and sex. Grandpa is part of the process too.

Caution: This Erotica Sex Story contains strong sexual content, including Teenagers   Sharing   Slut Wife   First   .

Bobby was so excited to have his driver’s license and an old but functional set of wheels. He looked for excuses to drive somewhere and this time it was to visit his widower grandpa across town.

There was a car he didn’t recognize in the driveway so he went around to the back door which was rarely locked and entered. Some odd sounds were emanating from the bedroom so he proceeded quietly and got both eyes full. He grandpa was naked on his bed and a girl was straddling his waist. The way she was moving, she had to be sitting on his cock!

The long-haired brunette was very young, probably close to his age. She was skinny and had breasts which were small but equipped with large and stand out nipples. He watched for a little bit because the two were focused on each other and hadn’t noticed him yet.

When his grandpa groaned and thrust his hips upward, Bobby surmised that he was ejaculating. The young woman bent down and gave him a quick kiss, and then dismounted and turned her head towards him. She squeaked in surprise. Grandpa turned to look and said, “Oh Bobby, I didn’t hear you come in.”

He didn’t seem embarrassed or flustered as he introduced Marie who he said was his sex surrogate and visited him twice a week. She calmly put her clothes back on, said she was pleased to meet him and left without further ado. His grandpa got up, wilted willie still wet with sex fluids, and walked to the bathroom. Bobby had to admit he looked pretty good for guy in his 50s.

After providing both of them with coffee, Grandpa smiled and said, “Yes, people my age like sex and since your grandma’s been gone I haven’t had any so that’s why this surrogate program sounded really good. As you know, your grandma was sick for a long time and so we couldn’t do anything intimate together and I’d lost confidence in myself in that department so even thinking about dating was scary to me. This was my third lesson and the first one that went ‘all the way’. I don’t know how many more I will get but I sure am enjoying the therapy.”

Bobby piped up, “I’d sure enjoy it too! She was the first naked girl I’ve ever seen. You suppose I could sign up for their program?”

Grandpa smiled and said, “If you don’t ask you don’t get, so I’ll tell you when she will be here next and will find out.”

They visited some more and Bobby went home to jack off to the images burned in his mind.

He was there early on the next day Marie would be visiting and they chatted a bit before she said, “It’s time for the therapy session.”

Bobby asked, “can I watch?”

She turned towards Grandpa and said, “I’m used to it so it’s up to you.”

The older man smiled and said, “I think it’s probably the best sex education technique I can imagine. Bobby, you just sit over in that chair and be real quiet. On second thought maybe you need to quietly walk around and see what’s happening from different vantage points.”

Of course Bobby had a hard on as he watched foreplay and then intercourse in two different positions. This time, when Marie disengaged she waved him over to the edge of the bed. “I know that this has been extremely arousing to you so let me relieve your tension.”

She was still naked, of course, and watching her unzip his pants and work his erection out made him harder than ever. He was amazed as she moved her mouth over the end of it and began the most pleasurable experience it had ever had. It would be, as she knew, only moments before she got a mouthful of his youthful semen.

When he erupted she swallowed and smiled at him, “You taste quite good so I bet your girlfriends must enjoy that.”

“I don’t have a girlfriend and I’ve never experienced what you just did.”

Grandpa had been watching this interchange and said, “Marie, perhaps you could teach him about sex.”

She smiled as she was putting her clothes on and said, “Of course I could but I’ve already had a virgin in my training. I’m an intern and we are supposed to have a variety of experiences. It’s enough of a challenge to get through them without adding more. I do have a girlfriend in the program who is looking for a virgin. Seems that they are hard to find these days, and I will let her know. If I can, I’ll have her come with me on your next session. How’s that?”

Both grandpa and grandson said that would be wonderful and they would look forward to it.

Cindy was a shorthaired blond, not as tall as Marie but a lot more filled out in all the places that women get curves. Bobby’s dick started to get hard in his pants as he was introduced. He took her to the other bedroom as Marie began her therapy work with Grandpa and they got at least briefly acquainted. Yes, he was a virgin and yes, he would be delighted to change that with her help. She had some paperwork he had to sign which he didn’t bother to read, anxious to get things going.

He didn’t get to bonk her that first time, since there really was an agenda that she was supposed to follow. He did get to touch and squeeze and suck her full and firm tits though, and she gave him a hand job to observe his ejaculation.

This was a good time in her schedule and so she would just accompany Marie on her visits. Grandpa was real interested in what it happened in the other room and smiled a lot as Bobby described what it happened and how he felt about it.

The next session moved into oral sex and Cindy got some satisfaction as she tutored. He was so proud of himself as he described their progress to his grandpa after the women left. He jacked off furiously to build up his endurance but abstained with great difficulty the morning that the next session would be.

This time they went to the foreplay quickly and she was smiling as he entered her in the classic position, thus making the transition to being a “man”. His ejaculation followed very quickly after that entry and she skillfully kept him inside her and soon ready for more. This time she showed him the advantages of a woman on top, especially one with substantial mammaries like hers. His ejaculation was not as quick but they still had time left so she sucked him back to hard and presented her hindquarters on her hands and knees so he could experience that approach to fucking.

There was one more session where they reviewed everything and then she could sign off on that part of her training. Bobby was infatuated with this young woman and asked how he might be with her again. He’d asked Marie for a date but she said she had a boyfriend who kept her occupied well enough when she was not doing therapy. When he asked Cindy she said that she wasn’t dating anyone and she’d enjoyed being with him enough that they could give it a try. She said it was best for her to come to Grandpa’s house and they set a time on a Saturday.

It wasn’t really what he’d been thinking about, a date, but if you got in her pants then that was what his goal for the dating had been anyway. They spent a couple of hours naked before she had to leave to go shopping, she said. When he asked about taking her out some evening, she said that she wasn’t available then and Saturdays were the best. It was a bit puzzling but she wouldn’t explain any further and he decided not to look a gift horse in the mouth, as the saying went.

Those Saturdays became a regular thing and they did have quite a bit of time to talk between couplings. She was rather guarded talking about her personal life but did explain about how she got into the surrogate therapy program. Her older sister was one and it seemed like a good fit for her interests and skills. So far she was doing well academically and in the field work. Bobby had kind of forgotten about that but wondered how many men had been inside her since he last was. It wasn’t a question he felt he could ask and he hoped she’d volunteer something but so far, no luck.

Then on a Saturday, before they stripped and screwed, he had a puzzling thing he needed to discuss with her. He’d been at Walmart during the week and saw her pushing a cart accompanied by a man. The ring that she always wore around her neck was on her left hand and he had one that was identical. It looked like she was married. Would she please explain.

Her eyes went wide and tears started forming. “Please, please, please, don’t tell anybody what you saw. I am married and you’re not supposed to be that in this program. At least not until after you graduate and get certified. They don’t want you to be too emotionally involved with anyone else because it might interfere with your field training and work. Casual boyfriends for sex and socializing are fine if you keep it that way and that’s what Marie does. I’d already been married a year before I decided to do this and I do have my husband’s complete understanding and approval, in case you wondered.”

That got Bobby even more puzzled, “Okay, I follow that but why are you dating me?”

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