The Education of RosebyBryanBiff©
I spotted her at Barbara's Bookstore. There were three teenage girls looking at a Playgirl centerfold and giggling. It was a hot day and all I was wearing a T-shirt, cargo shorts, and sandals. I admit that I got a bit turned on watching those girls ogling the naked stud in Playgirl and I had to shift my penis to avoid having an obvious hard-on. Hey I'm a healthy 21 year old. I get hard pretty easily.
This old lady - she looked at least my grandmother's age - was standing off a little to the side watching the girls and trying to peer over and see what they were looking at. When they put the Playgirl back on the stand (in the wrong place), she looked at it, but didn't quite have the courage to pick it up herself. Then she saw me looking at her and kind of blushed.
"Hi," I said.
I reached over and picked up the Playgirl and moved it to the right spot.
"Girls today are very forward," she said out of the blue.
"What do you mean?" I asked.
"When I was young, a young lady would never look at .. pictures like that."
"You mean pictures of naked guys?" I said.
I laughed. "Well we guys look at girls, so I guess they should have the chance to look at us."
She scanned my body pretty carefully and when I turned around to leave, she introduced herself.
"My name is Rose," she said.
"Hi, I'm Bryan."
We sort of stood there awkwardly for a moment. Then she said, "Bryan, would you have a moment to have a coffee with me," she said. "I don't get a chance to talk with a young man very often."
Was she trying to pick me up? This old lady? "Yeah, ok," I said.
But when we went across to Caribou and sat down with our coffees I began to wonder. She just started talking about the weather, the bookstore, and anything else to cover up her nervousness.
I said, "So you think girls today are forward?"
She smiled. "Well pictures of men ... like that ... were unheard of in my day. One didn't admit to wanting to see such things."
"But you did right?"
"Well," she smiled. "There's always a bit of curiosity."
"I was for 35 years," she said.
I shrugged, "Well ..."
After several minutes of hemming and hawing it came out that she had never seen her husband nude once in 35 years. They made love in the dark under covers and eventually not at all and slept in separate beds. "My God," she said, "I'm telling you things I've never told anyone."
"If you want to look at guys, you could just subscribe to Playgirl," I said, "and save yourself the trouble."
"Oh my, and have the doorman and postman know?" She shook her head at the thought.
I laughed. "Nudity is not such a big thing."
"Maybe not for your generation," she said.
Then she actually took my hand, looked into my eyes, and said, "I envy you, your youth and free spirit." By this point I was pretty sure she wanted to see me naked: like that was the whole purpose of the conversation. And there was something about the thought that was kind of thrilling in a way. I mean, there was totally no attraction to this old lady, but I sort of dug the fact that she was so into me and had gone her whole life without really seeing a naked guy.
We bantered a little longer. She didn't want it to end, so whenever there was a lull in the conversation, she started something else. Its like she hadn't talked to anyone for a year. She started to edge the conversation toward the area: she said she lived nearby in one of the high rises.
"Is it a nice place?" I asked.
"Oh yes, very comfortable, I've been here for more than 30 years."
Then a pause.
"If you'd like, we could continue our conversation there."
Now I was sure about what she wanted.
I looked at my watch. Then after a few second I said, "well ok, sure."
She seemed delighted.
It took 15 minutes to walk the three blocks to her place: she took forever. The building had a doorman, who greeted us. She introduced me as Bryan "who will help with some work around the house" as if the doorman needed to know. Then we took the elevator up to her place, which was pretty nice in an old lady way and had a nice view of the lakefront.
We went into her den and I sat down on the couch. She sat in an adjoining chair and turned on the TV. We sat there awkwardly.
"You really are quite handsome," she said. "You must be a college athlete."
I laughed. "Not really, no. I swim, that's about it."
More awkward silence. Was I wrong about what she wanted? She was so reserved, it was hard to tell.
I decided to break the silence.
"Rose, if you want to see more of my body, you can just ask."
"Would you, Bryan?"
"Yes, Rose, but just for show, ok? I don't want anything to happen between us."
"Oh .. yes, of course, yes ... no, no, nothing like that, " she babbled.
"OK," I smiled. "Then tell me what to do."
She blushed. "Oh my..."
She motioned me into the den and put on the light. Then she sat down and looked at me, almost worshipfully.
I stood there motionless. "Rose, do you want me to take off my sandals?"
She nodded. I unbuckled them and kicked them off, standing before her in bare feet.
"Rose, do you want me to take off my T shirt?"
Again she nodded.
"Bryan ..." she said haltingly. "Please take off your shirt."
I pulled it over the head and tossed it on the floor.
"Your skin is so smooth," she said. "You have a beautiful physique, like a statue."
I laughed. "Not too thin?"
"Oh no," she said. "Just right."
She looked down and saw the small trail of light brown hair that started below my stomach and worked its way down.
"Bryan, would you mind removing your ..." she paused for a moment. "Trousers."
I slowly unbuckled my belt and let my cargo shorts fall to the floor. I kicked them away. I was wearing blue boxers.
"Like my shorts?" I asked.
"Oh yes, very attractive," she replied, gazing in wonderment.
Then she offered to bring me a beer, which I accepted happily.
She came back with the beer and I took a couple of swigs. I walked around the den and looked at some of her family pictures. I put the beer down on a coaster and looked at her.
"Rose, I can pull down my shorts if you want me to."
She breathed in for a moment. "Bryan do you mind .. that is... would you please take off your ... underwear."
"I'd be happy to, Rose." I pulled my shorts down very slowly, letting her get a good look at my public hair, and then letting my penis kind of bounce up out of them. I stepped out of my shorts, kicked them away, and stood naked before her.
I took another swig of the beer.
"Do you like seeing me naked, Rose?" I said.
"Why yes," she said. "I really do."
I laughed. "You seemed surprised."
"Well I really wondered if I would like seeing ... a boy," she corrected, " a man like that ... and .. well. you're just exquisite."
"Why thank you Rose."
"You could pose for that magazine."
I laughed. "I'm not sure I'm ready to have the whole world see it" and then I put my hands over my dick for a second.
The combination of the beer and her intense gaze started to cause my dick to visibly twitch. Before her fascinated eyes, my penis started to harden, lengthen, and arc toward the ceiling.
"Are you getting ...?"
"Yes, Rose," I smiled. "I have an erection. Enjoy it."
Moisture collected on the tip of my dick. I looked down and then at her and said, "Precum."
She looked quizzically.
"When I get hard, my dick oozes precum."
The explicit language shocked and intrigued her. "See how wet my dick is?"
I lifted it to show her. "Do you mind if I masturbate? Otherwise this thing will never come down."
"Bring me a towel," I said.
By the time she returned with a washcloth, I was stroking my dick very very slowly. But I could feel the buildup.
"I'm going to come now, " I announced and squirted my juice onto to cloth and a little onto the carpet.
I handed her the cloth back and stood there with my cock dripping.
After a few moments I felt other urges. "Rose, I have to go to the bathroom" I said.
As she led me back into the apartment, she watched intently as my still hard dick bobbed up and down while we walked.
She opened the door and turned on the light revealing a rather large bathroom, with a shower, separate tub, and toilet. "Rose, I have to take a piss." I said. "You can watch if you want."
She looked at me in amazement.
"Bryan," she asked, "don't you feel at all self-conscious?"
"A little, yea," I admitted, "But I'm getting juiced just watching your reaction."
I positioned myself in front of the toilet naked.
"I have to wait until my hardon goes down," I explained to her.
She watched with fascination as my dick slowly went down. She seemed completely embarrassed and yet she couldn't turn away. I pointed my dick toward the bowl and she watched the first few drops of piss come out, followed by a full stream, splashing loudly.
"Rose, can you hand me some toilet paper."
She did and I wiped a few drops of piss off my dick.
I smiled at her. "Hey Rose I think that's a first for me. I don't think I've ever peed in front of a woman before."
"This is a day of firsts," she said and chuckled.
"Rose," I said, "I need to get cleaned up."
"Do you need to take a bath?" she asked.
Well actually, I was thinking a shower, but why not? Give her one more thrill. Watching me take a bath like a little boy.
"Yes, Rose, may I take a bath?"
Rose dutifully ran the water and gave me a towel and a fresh washcloth and bar of soap. I got into the bathtub, water coming up about halfway. Rose sat on the edge of the tub.
"You're a wonderful boy," she said.
"And you're so clean."
"Oh yes," I said, "clean."
I started a running narration.
"First I wash my feet and I make sure to get in between my toes. Then I work up my legs. See Rose?"
She smiled, taking it all in.
"Then I wash my chest and neck."
"Rose, do you mind doing my back?"
She ran the soapy washcloth across my back and neck very gently.
"Thanks, Rose." I said, squeezing her hand and taking the washcloth back.
"Now I have to wash my pubic area and penis very carefully."
"Oh yes, Rose, it's very important for boys to be clean down there."
She watched carefully as I scrubbed the shaft and head of my cock and my balls. "I'm cut - circumcised - so its easier to stay clean, but I still have to wash daily. I want to make sure my piss slit is clean." I knew my language would shock and intrigue her.
"Is that area very sensitive?" she asked.
"Yes, definitely, Rose. After cumming, a boy is quite sensitive down there."
Then I leaned back in the tub and lifted my legs . Rose looked at the trail of hair leading below my balls into my crack and she inhaled deeply. I spread my legs as far as I could.
"Rose I'm going to clean my hole now." Her eyes grew as she watched me make myself totally vulnerable to her gaze. Slowly I ran the washcloth between my asscheeks.
"I imagine young men must have to be clean that area quite often."
"Oh definitely, Rose," I said, my legs still in the air. "You'll notice I have some hair around the area of my hole..."
"Um, yes, Bryan."
"...so I have to clean around my hole very carefully so nothing gets, you know, stuck down there."
"Oh yes of course you do."
I got up and started toweling off.
"May I?" she asked.
"You want to dry me off?"
I stood a head taller than her so she had to reach to dry my back and chest. Then she lifted my feet and she dried them off and started working up. Very carefully she ran the towel over my ass, and then my dick and balls. She looked up at me. "May I?"
I nodded and she touched my penis. I gave a Rose a kiss on the cheek. Her touch caused my dick to twitch again. "Well look at that Rose. You made my penis hard again."
"Why yes," she said. "I did." My dick was sticking straight out.
"Rose, would you like to masturbate me?"
"I've never done that," she said.
"That's ok," I said. "I'll show you." I took her small hand and wrapped it around my hard dick, which was now curving upward. With my hand over her hand, we started pulling on it. Then I took my hand away. Rose kept pulling on my dick. The scene was ludicrous: both of us in the bathroom, Rose, age 70 fully clothed, me Bryan , age 21, naked and hard. She looked at my penis then up into my eyes. I smiled. "Isn't this fun, Rose?"
She smiled back. Then I moaned and - spurt spurt - ejaculated into her hand. She was practically shaking. She quickly washed her hand, then very gently toweled off my dick. It had been quite an education for Rose that day.
She watched me get dressed and leave. About eight months later we ran into each other again at the bookstore. It was winter and I was dressed quite differently, but she recognized me at once and blushed furiously. "We had a grand time," she whispered to me.