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This story involves a young man who is a virgin, and a woman over three times his age. Therefore, this is both a “first time” story and a “mature” tale.


This wasn’t the way that most guys my age want to spend the summer before heading off to college, I recall thinking as I looked out the kitchen window to the tiny yard and the postage stamp lawn that might take me all of a minute to mow tomorrow.

The house and the yard had belonged to my grandmother, who had been in and out of the hospital for the last couple of years, and had finally succumbed to a variety of illnesses last week at the ripe old age of 82.

While much of the rest of my family had abandoned Grandma, I had continued to visit her in her declining years, which was how I ended up with the dubious honor of going through her stuff and shutting the house down so that it could be sold.

It was while I was taking a break from the house cleaning that I saw the woman who had lived next door for as long as I could remember, puttering around in her back yard. All I really knew about her was her name, Anna.

She was a tiny woman who lived alone in the modest bungalow at the end of the street, nestled between the woods and my Grandma’s place. She looked older than I remembered when I had seen her last year, her black hair now more streaked with grey and pulled back in a bun.

When she saw me, she gave a timid wave before heading over to the fence. I went out to meet her. After she expressed her condolences about my grandmother’s passing, she asked about what was going to happen to the house.

“I don’t know,” I said. “They just sent me here to try and make sense out of her belongings. My folks and the rest of the vultures will take what they want, and then I guess the place will get sold.”

“New neighbors,” Anna said, shuddering visibly. “Just the thought of that bothers me. I was so used to your grandmother. She was such a nice lady. I guess we got along pretty well because we were alike in many ways. She loved you very much, but you know that. She always said that Tommy was her favorite – the only one that would bother with her.”

“Oh, I don’t know about that,” I mused, but had to admit that Anna was right.

“It was good that she had someone that cared about her,” Anna said softly. “Being alone is…”

Anna left the sentence unfinished, but I sensed that she knew what being alone was all about. I had never seen anybody besides her next door, and while I recall Grandma saying something about her being married at one time, I gathered that her husband had passed away.

After we chatted for a few more minutes, Anna asked me if she would like to come over for dinner. I had mentioned that I had been depleting Grandma’s cupboards during my stay, and when the tiny woman invited me, I realized I had backed myself into a corner and so I accepted.


Much like my grandmother’s house was, Anna’s felt like a museum to me, with all of these little nick-knacks and doilies all over the place. I had gotten as dressed up as the limited wardrobe I brought here would allow, and after Anna complimented me on how I looked, she brought me into the kitchen for dinner.

Gradually, my nervousness faded as we began conversing. We kept the topics light and avoided talking about my Grandma, and after I helped my hostess with the dishes she brought me into the living room.

At that point, I have to admit that I was trying to figure out the most graceful way to end the evening. Anna was very nice and all, but I figured she had to get to bed early like Grandma always did.

“Do you have any children?” I asked as we sat on her couch, which was probably older than I was, and found my eyes going to Anna’s legs for some reason

The pale limbs were very slender, and the fact that they weren’t all that bad for a woman her age probably got my attention for longer than they should have, because she caught me looking at her as she answered.

“No, I – we couldn’t have children,” Anna said sadly. “I wanted children so badly. My husband – he did too. That why we – he left me.”

“Oh,” I answered, regretting that I had picked the wrong topic for conversation. “I’m sorry. I didn’t know.”

“Not your fault,” Anna replied, patting me on the arm and giving my limb a little squeeze. “Anyway, I suspect that you must be a very responsible young man, seeing as how they left you in charge of gathering everything up and all.”

“If anybody suspected that Grandma had anything of value, I’m sure the vultures would have swooped in,” I opined. “So far, I’ve found about a dollar in pennies and about a dozen empty bottle of seltzer water.”

“Don’t spend it all in one place,” Anna suggested, and I shared in her laughter.

Anna had an adorable laugh, as petite as the woman it came out of, and as we talked I found myself getting more attracted to her. I wanted to ask her how old she was, because it was hard to tell from her appearance. I suspected that she could be anywhere from 55 to 75, although the fact that she still worked made me lean tandoğan escort toward the lower end of that scale.

There weren’t very many pictures around, but there was one of Anna when she was very young, probably in her twenties. She was a cute woman back then even if the picture looked like something from the twenties. Even then Anna had her hair in that little bun, which made her look a bit like a spinster.

“What grade are you going to be in next fall?” Anna asked when the conversation turned to me, and when I told her that I was going to be a sophomore in college she got flustered.

“Oh, I’m sorry,” Anna said apologetically when I told her I was going to be 20 next winter.

“I know I look like a kid,” I offered, knowing that my nerdish appearance made my age tough to figure out.

“No, it isn’t that,” Anna said. “It’s just that your grandmother – the way she spoke about you, I always got the impression you were still a child.”

“I don’t think Grandma ever understood that I was getting older,” I admitted. “I was always afraid that for Christmas she would give me something like those pink bunny pajamas that Ralphie got in The Christmas Story.”

Anna started giggling at that, and squeezed my arm as she leaned against me, coming so close that I could smell the ancient perfume she used, a pleasant scent but something that seemed from around era.

“As a matter-of-fact,” Anna said when she stopped laughing. “The way you act – you’re very mature. It’s almost like you’re older than your years.”

Anna had a point there, I admitted to her, because I always seemed to relate well to people older than me.

“I’m square,” I confessed. “Maybe I was born too late, because I don’t like the stuff I’m supposed to like. Stuff guys my age are into, like rap music and reality television – things like that. I’d rather watch MASH or The Honeymooners than any of the junk that’s on the tube these days.”

“There’s nothing wrong with being square,” Anna told me, motioning toward the television that looked as old as me. “I hardly ever turn it on, except for the news. So, do you have a lady friend?”

“Me? No,” I said.

“I’m sorry. I shouldn’t be so nosy,” Anna said. “I mean, you might not even be…”

“Interested in girls?” I said in finishing her thought. “No, I’m very interested in girls.”

“Good,” Anna said blushing. “I mean, whatever you like is fine, but you never know these days.”

“That’s okay. No, I like girls but the feeling is not nearly as mutual as I would like,” I confessed.

What would she say if she knew that the only memorable relationship I had ever been in was with my science teacher, a woman who had been twice my age. A woman as plain and shy as I was, and she was about to take my virginity when she suddenly felt guilty. Her getting cold feet at the last minute was a crushing blow that I still hadn’t gotten over.

“I’m sure you’ll find the perfect girl someday, Tommy,” Anna said softly. “There’s still a place for good-hearted and considerate guys, no matter what you might think. Not all of us like the ‘bad boys’, you know.”

I happened to look at the clock, and when I asked Anna whether that was the right time, she seemed as surprised as I was that it was just past midnight.

“Silly me,” Anna said. “I’ve been babbling away all night, and you’ve been so sweet to sit there and put up with me.”

“I’ve had a great time,” I assured Anna, and I wasn’t lying, because what I had feared might be torture was instead a fun evening. “Really.”

“Will you be heading home tomorrow?” Anna asked, and the more I thought about it, the less good that idea sounded.

“I think I’ll probably be here at least for a couple more days,” I said, stretching the truth a bit when I added, “There’s a lot of stuff I still haven’t gone through yet.”

“Would you like to come over for dinner tomorrow night then?” Anna said, and immediately realized how excitedly she had offered the invitation.

“I mean, if you’d like to, that is,” Anna added. “I promise not to keep you so late tomorrow.”

“It’s a date,” I said as I went to the door, and when I opened it I paused, thanking Anna for a great night.

“Thank you, Tommy,” Anna said, and when I gave her a little hug she not only returned it, but gave me a little peck on the cheek, reaching up as high as her head could reach to press her lips to my cheek.

So tiny, I thought as I squeezed her and felt her frail form, although the press of her breasts against my stomach got my attention. When I got back to my grandmother’s house I closed the door and leaned against it for a moment, wondering what the hell was wrong with me.

There I was, a 19 year old geek not only spending an evening with a woman who, if she hadn’t reached senior citizen status yet, could see it from where she was, and not only did I enjoy myself, I even got a hard-on from hugging her.

“You’re a sick fuck, Tommy Baldwin,” I said aloud as I went into the kitchen for a drink of water.

After quenching tunalı escort my thirst, I realized that I was not going to get to sleep right away, so I did a little housekeeping, bringing a few empty boxes into the spare bedroom that I always stayed in. On my way in, I happened to glance out of the window that faced Anna’s house as I reached for the light switch, and found myself setting the boxes down and not turning on the light.

Instead, I moved through the dark room like a cat when I saw the light on in the house next door. The curtains were open, with only the sheers shielding my eyes from an unimpeded view of Anna Hayward’s bedroom.


“Sick sick sick,” I heard myself muttered as I looked over at the woman who I had just shared my evening with, and when I first glanced over I saw Anna in the process of putting her nightgown on, which meant that I had arrived just a little bit late.

It was a very plain nightgown that revealed little, but with the house less than ten feet away it was almost like being there, with the sheer curtains giving Anna’s bedroom the look of an old-time movie.

Her china white arms were so slender and pale, yet were surprisingly trim, with little of the sagging of skin that many women get as they age, and I would have seen it since she was busily brushing her hair after freeing it from the bun.

Sitting at what looked like a little make-up table, Anna worked the brush through her wiry hair with her right hand as she used her left hand to hold it down. My mother used to brush her hair 100 times each night, and I hoped that Anna did as well.

She looked a little like Katherine Hepburn, so fragile and feminine looking despite tiny wisps of dark hair that sprouted from under her arms. The unusual sight of a woman with unshaven armpits did not offend me, and in fact the effect of seeing the little patches of fur was just the opposite as I stood there peeking though the blinds like a pervert while she did what was likely a nightly routine.

Five minutes later the light in Anna’s bedroom went out, and the sudden darkness seemed to break me out of the trance I was in, leaving me to assess what I would look like had Anna been looking over this way.

Nothing unusual here, I thought. Just Tommy Baldwin with his jeans and underwear down around his ankles, his right hand still pulling on his deflating dick while his left hand was filled with the end result of his orgasm.

Perfectly normal. Nothing I hadn’t done countless times before, except this time the target of my deviant thought was a perfectly charming and innocent mature woman who, if she had ever see what I was doing, would have been just as disgusted with me as I was with myself.


I ended up at Anna’s again the next night, and I found myself having a great deal of trouble looking her in the eye as we ate dinner. Anna asked me if I had a productive day and I lied and said I did. I wonder what she would have thought about me had she known what I did?

“Let’s see,” I could imagine myself saying if I was pumped full of truth serum. “Last night when I got back to my grandmother’s house I thanked you for you kindness and hospitality by peeking at you through the blinds as you got ready for bed. Violated your privacy in a way that I’m sure has never been done to you before.

I masturbated while watching you brush your hair, and then after I woke up the next morning I was looking out the front windows when you left the house to catch the bus to go to work. Did it again – jerked off I mean – while watching you walk past the house, wishing that your dress was shorter so I could see more of your legs.”

I could not imagine what this sweet old lady – and there was no denying that Anna Hayward qualified for that word – would think about such a confession. Yet as I finished another nice meal I couldn’t at least say something.

“Uh – you know Anna,” I said as I leaned back from the table. “When my grandmother’s house gets sold, you might want to, you know, like in the back…”

“I’m sorry Tommy,” Anna said after trying to decipher what I was trying to say. “I don’t understand.”

“I mean, your bedroom,” I stammered, wishing I hadn’t started this but was too far in to stop now. “From the spare room in back, you can see into your bedroom.”

“Oh dear,” Anna said when she finally figured out what I was saying. “The curtains – I leave them open for the sun – oh no!”

“I’m sorry,” I mumbled when I watched Anna’s pale complexion turn crimson. “Just thought you should know, like for the future.”

“Yes, thank you,” Anna said before excusing herself and scurrying out of the room.

I knew where she was going. She was running back to her bedroom and closing those curtains after looking out to see exactly what I had seen. So much for the hope, the crazy thought that she had opened those curtains for me to look at her through.

“There,” Anna said when she returned, trying to act like nothing had happened.

“I hope you aren’t mad at me,” I said.

“Mad? Oh turangüneş escort my no,” Anna said as I helped her clear the table. “Can you imagine what someone just moving in would think? Glancing over at seeing a 63 year old woman prancing around naked?”

That answered the question about how old Anna was, but once again I couldn’t shut up.

“I didn’t see you naked,” I said.

“That’s good,” Anna sighed. “You wouldn’t have come over for dinner if you had.”

“I wished I had,” I blurted out. “Seen you naked I mean. You had just put on your nightgown when I noticed your curtains were open.”


“You sat down at your dressing table and brushed your hair,” I continued.

“That must have been something to see,” Anna said as she dropped a saucer in the sink, clearly confused at what I was saying.

“It was. I watched you brush your hair until you got up and turned out the light,” I admitted, leaving out the other part. “You looked so beautiful that it looked at I was having a dream.”

Anna put her hand on the edge of the sink, steadying herself, and she looked as if she was going to faint.

“Tommy, you…” she started to say and then stopped. “You’re a sweet boy but I know what I look like now. If I was 50 years younger, you might have gotten a more pleasant sight.”

“I didn’t wish you were younger. Maybe I wished I was older,” I said, making little sense. “I better go before I make an even bigger fool of myself.”

“Don’t go,” Anna said, clutching my forearm with her weathered hand. “I don’t – would you sit on the couch with me for a moment?”

I nodded and helped her into the living room, sitting next to her on the couch and asking her if I could get her something.

“No, just sit with me for a minute,” Anna said, our knees touching.

The only sound in the room was the ticking of a clock somewhere behind us, and as Anna seemed to regain her composure I got relieved.

“I’m really fine,” Anna assured me after I asked again. “That was a lot of things to digest at once.”

“I shouldn’t have said anything,” I said. “I just felt guilty about spying on you like I did. Even if I didn’t set out to do it, I still could have just turned away when I first saw you, but I didn’t.”

“No wonder your grandmother loved you so,” Anna said, her eyes watering. “I wish I had met someone like you when I was young. Those things you said, no matter how crazy they sounded, I still loved hearing them. Nobody has said I was beautiful in – I don’t know how long ago.”

“You are beautiful,” I said, taking her hand in mine. “Guess you can tell I’ve got a crush on you.”

Anna giggled at that, and squeezed my hand with hers as she looked at me.

“You’re going to make somebody a wonderful husband someday,” she said.

“I don’t think so,” I said. “I don’t belong here – I don’t mean here – I mean in the 21st century. Girls my age just don’t do anything for me. Someone like you I can spend hours talking to and listening to, but girls my age? I listen to them babbling about stuff I don’t care about for two minutes and I’m tearing my hair out.”

I went on to tell Anna my entire life story when it came to girls, and because there was so little to tell and the tales were so tame, even Anna didn’t flinch.

“I was crazy about her,” I said of my science teacher and of her last second guilty conscience, and then I told Anna something that I never shared with anyone before or after.

I shared with Anna the story of my dating Jill, and how when it finally got to the point that guys dream about, this time it was my fault it didn’t happen.

“We got naked and when she saw me – my – you know, she giggled,” I confessed, the memory still as fresh as if it was last night instead of last year. “I’m – It’s kinda small.”

“That sort of thing doesn’t matter,” Anna said softly. “Maybe she was just nervous or something.”

“Yeah, maybe,” I agreed, although in my mind I saw it differently. “After she laughed when I tried, I couldn’t – you know.”

“So you’re a virgin,” Anna concluded, and I nodded. “It’s nothing to be ashamed of you know. Even I was one once myself.”

We laughed at that, but then Anna continued.

“I was a child of the 60’s,” Anna explained. “Back then I was probably just as silly as the girls of today are. Smoking grass and drinking Boone’s Farm wine.”

“You did?”

“I did indeed,” Anna declared. “I wasn’t as crazy as a lot of people my age, but I was no wallflower either. If I told you how I met my husband you would die.”

“Tell me.”

“I couldn’t,” Anna said. “Let’s just say that it wasn’t something I’m all that proud of now.”

I kept after her, reminding her that I had just told her every one of my many humiliating experiences with the opposite sex, and finally she gave in.

“I went to a concert at the Aerodrome with a girlfriend of mine,” Anna explained. “This was in Schenectady, New York, and there was this group that had just came out called Led Zeppelin.”

“Led Zeppelin?” I said – shouted. “You’re kidding!”

“No. My friend Peggy was a little older and knew more about music than I did, so I went along with her. Hitchhiked and ended up sitting on the floor of this old bowling alley or whatever it was, about 15 feet away from these really skinny guys with long hair who I had never heard of.”

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