My Neighbor's Daughter

My name is Ray, and I've lived alone in a 2300 sq. ft. ranch-style house since my wife Ann passed away in a tragic accident. While a hefty lawsuit settlement has left me financially secure for the rest of my life, all the money in the world couldn't help my loneliness. I still maintain some income from being a freelance writer, but I treat it more as a hobby and something to keep myself busy. I like to play golf and have some beers with my friends, and I attend various sporting events and concerts to pass the time.

I work out every day at the gym to stay in decent shape. I'm nowhere near being a bodybuilder, but I'm toned and in good shape for my age. I have a little bit of a beer belly, but not as bad as most guys my age. It took me a few years to start thinking about dating again, but I'm in my early fifties, and the pickings are slim.

Friends have tried setting me up with women they know, but that hasn't worked out well at all. I wish they would stop trying so hard to play matchmaker and let nature take its course. I've tried online dating, and that hasn't been any better than matchmaking friends. Part of the problem is that I'm not looking for a serious relationship right now or maybe ever. Most of the women my age are looking for a husband, and that's when I run for the hills. I've had a few friends with benefits relationships, but when they started to get serious, I broke it off with them.

More often than I want to admit, I'm left to jerk off to my fantasies while watching Internet porn. It's less complicated than trying to date while I'm in my fifties. Don't get me wrong, I'm not jerking off every night, but sometimes, a guy needs to release the pressure in his balls. I like to have a beer and watch sports on TV out on my back patio. I have a nice inground pool with a diving board and hot tub that I enjoy regularly.

There is a young couple with an infant child on one side of me and a couple around my age on the other. I don't have much of a relationship with either neighbor, but I know the older couple better since they've been there longer.

Felix and Helen have three grown children. Gretchen is the youngest and is finishing up college. I've talked to them over the years, but we don't share many interests. Felix is a computer software engineer, and Helen is a Math professor at a local university. I don't want to call them nerdy, so I'll say they are scholarly. I've had friendly conversations with both of them, but it's not like I can talk sports or play a round of golf with Felix. They don't drink much, so we've never hung out and had a few beers either.

It has been said, "The apple doesn't fall far from the tree," so it isn't surprising that their children are a bit nerdy, er, scholarly, too.

While most kids were going to summer camp to fish, swim, play sports, and tell stories around the campfire, their kids were off to physics or astronomy camps. Hey, to each their own. I'm not going to judge anyone, I'm only trying to give the readers some perspective.

One early summer day, Felix stopped to talk to me while I was out cutting the grass.

"Hi, Ray."

"How's it going, Felix? What's up?"

"I just wanted to let you know that Helen and I are going to be taking a six-week trip through Europe starting next week."

"That's great, Felix. I hope you two have a great time."

"Gretchen is going to stay at the house while we're away. Even though she's twenty-one, I was hoping you'd keep an eye on her and help her out if needed."

"No problem. I'd be happy to help out in any way I can."

"Thanks, Ray. Even though she's an adult, we still worry about our kids. It's nice to know she can go to you if she has to."

"You're welcome. Tell her she can call me any time."

I'd see Gretchen coming and going from her parents' house during her school breaks, but I hadn't talked to her in years. It's not like we communicated a lot anyway. From what I could remember, she was average in height, maybe carrying a few extra pounds, but it was hard to tell because of the way she dressed. The best way to describe her attire is frumpy. She wore long skirts or dresses, or baggy clothes. She wore glasses and kept her hair in a bun most of the time. She resembled the stereotypical librarian.

I almost forgot about my neighbors going out of town until I saw Gretchen coming and going from the house. She hadn't changed much since the last time I saw her. She was dressed in the same frumpy manner. Her dark brown hair was in a bun as usual, and she was wearing a sweatshirt and sweatpants.

Things were pretty quiet around the house for the first few days, but then I saw Gretchen having a hard time starting the lawnmower, so I went over and gave her a hand. It wasn't a big deal, anyone would have given her a hand. Later that same day, her car wouldn't start, so I tried to give it a jump start, but that didn't work. I drove her to the auto parts store to get a new battery and installed it for her.

Gretchen was so appreciative, she told me, "I don't know what I would have done without you today, Ray. Thank you so much."

"You're welcome. I'm glad I could help out. I promised your parents I'd look out for you while they were gone."

"Normally, I don't like them treating me like I'm still a kid, but it worked out for me this time."

"If you ever need anything, don't hesitate to ask me for help."

"Thanks, Ray, I feel like I owe you something for helping me today."

"Ah, you don't owe me anything. It was my pleasure."

"How about if I cook you dinner? I don't have any plans."

I thought about her offer and replied, "How about if we have dinner at my house. I have a pool and a hot tub. We can throw something on the grill and enjoy the nice weather."

"Yeah, that sounds like fun. I'll bring over a couple of strip steaks, and I'll make pasta salad."

"Sounds good. I have plenty to drink too. Soft drinks, beer, or wine."

We had our plans set. Gretchen was going grocery shopping, and when she got back, she would come over. I was happy to have some company to break up the monotony that my life had become.

After spending a good portion of the afternoon with Gretchen, I noticed that behind the glasses, hair in a bun, and frumpy clothes, she was kind of pretty. She was shy in a cute way, with a genuine way about her. There was nothing phony about her. I was looking forward to spending the evening with her.

I straightened up the house and anxiously awaited Gretchen's arrival. I knew it was silly, but I couldn't help myself. I smiled when I heard the doorbell ring. She was wearing an oversized long-sleeved t-shirt and loose shorts.

After I welcomed her inside, I asked, "Did you bring a swimsuit?"

"Yeah, I have it on underneath."

"Good, because that's the first thing I wanted to do. It's hot out there."

"Yeah, I was looking forward to cooling down, too."

After we put the food in the fridge, Gretchen told me she'd like some red wine, so I grabbed a bottle and headed out to the pool. When we got outside, I took off my shirt and waited for my guest to get ready. She seemed a bit shy about taking her outer clothing off, so I jumped into the pool so she wouldn't feel too uncomfortable. I'm a normal guy and was curious to see what she looked like in a bathing suit.

Gretchen was wearing a very modest one-piece swimsuit. It was more fitting of a woman much older than a woman her age. Her swimwear showed no cleavage at all and fully covered her ass. She had pale white skin, and I could tell she wasn't confident in revealing even a small portion of her body.

However, it appeared that Gretchen might be hiding a decent-sized pair of breasts and a well rounded ass that led to some thicker thighs.

I remember thinking to myself, "Uh, she's got a decent body. Too bad she's been hiding it all these years."

She took off her glasses and let down her hair. I don't recall ever seeing her with her hair down before. Gretchen walked slowly down the stairs and waded into the pool before fully submerging herself in the crystal clear water.

"Oh, it feels good to cool off in your pool, Ray. Thanks for inviting me."

We'd swim around and then go to the side of the pool to sip our wine before swimming around again. We were also chatting about her studies and how she also wanted to be a college professor as her long-term goal. She asked me about my writing and some of my hobbies. It was nice to have a conversation with a young lady. It made me wish I had gotten to know her better before that night.

When we got hungry, I fired up the grill and put the steaks on. Gretchen covered herself with a towel as I was grilling the steaks. We had another glass of wine over dinner. She told me she wasn't much of a drinker; she normally stopped after two, but felt pretty good that night.

Gretchen seemed to be relaxing and enjoying herself, and decided to have a third drink while we soaked in the hot tub after dinner. At times, she would get warm and sit on the edge of the hot tub to cool off.

I don't know if it was the alcohol or the fact that I hadn't gotten laid in a while, but I started looking at Gretchen in a more sexual manner. Even though her swimsuit was anything but sexy, I was still checking out her bare legs covered in droplets of water. I was trying to imagine what her breasts and ass looked like. I would sometimes feel guilty for looking at her like that, but the guilt didn't last too long.

At one point, Gretchen asked me, "Is everything okay?"

"Yeah, why do you ask?"

"You keep looking at me."

"For one, you're the only other person here," I said with a chuckle, "and two, I've never seen you with your hair down before. You should do that more often. You look nice with your hair down."

Gretchen blushed a little and replied, "Really, no one has ever said that to me before."

"You have really pretty blue eyes, too."

She gave me a forced smile in response, and I could tell she was uncomfortable with my compliments, but I was sincere in my comments. Gretchen changed the subject as we relaxed. It was nice to have someone to talk to. I had spent many lonely nights in the pool and hot tub. When Gretchen told me she had to leave, I was disappointed and figured she didn't want to hang out with an older guy.

Before she left, I told her, "You know, you can come over anytime you want and use the pool or hot tub. Even if I'm not home, you're always welcome."

"Thanks, Ray. I'll remember that. I had a nice time tonight. Thanks for inviting me."

"I had a great time, too. It was nice talking with you."

I watched as she dried herself off while further admiring her youthful body.

From that day forward, Gretchen and I would talk often, either in person or by text messaging each other. We'd get together to swim or to have meals together. Sometimes it was a morning, coffee, lunch, or dinner. We were becoming quite close. I especially liked the time we spent in the pool.

As we got closer, we felt more comfortable with each other. I told her about how devastated I was to lose my wife at a relatively young age, and she shared that she wasn't that experienced with men and dating.

One evening while we were sitting around the pool having some wine, I told Gretchen, "I hope you don't mind me saying this, but you're a naturally beautiful woman."

She scoffed at my comment and replied, "Alright, if you say so."

"No, you really are. I don't like it when women pile on the makeup. They seem so phony. You're pretty without all the fake stuff. You should have more confidence in yourself."

"I don't feel pretty, and I'm fat."

That's when I scoffed at her comment, "Why do women think they're fat? You look great."

"I've got a fat ass and my boobs are small, not a great combination for attracting guys."

"You've got a nice ass and your breasts are lovely," I replied but realized afterward that I just admitted to checking her out.

"You're just saying that to make me feel better."

"No, I'm not. If you don't mind me saying it, you should consider dressing a little more fashionable."

"No one wants to see my body."

"Oh, I for one, ah, never mind," I started to say before I caught myself. I didn't want Gretchen to think I was looking at her in a sexual manner, even though I was.

We quickly changed the subject, but I could tell she was flattered by my comments. She stayed for another half an hour before saying goodnight.

I went inside to change, have another glass of wine, and catch the end of a ball game on TV. As I was walking by the spare room that I used as an office for writing, I noticed a light come on in one of the bedrooms next door. The shade was up, so I could see into the house. Holy shit, it was Gretchen's room.

I told myself, "Don't look, just go get dressed."

That thought lasted for a split second until I saw Gretchen start to take off her swimsuit. I was frozen in place, hypnotized as I watched her peel down the top of her swimsuit. Oh my goodness, her breasts were even better than I imagined. I moved to a dark corner of the room so she wouldn't see me watching her.

Her breasts were beautifully formed, round, firm, and full. Her nipples were very dark and hard. She pinched them a couple of times and brushed her hands across them while looking at herself in the mirror attached to her dresser. Gretchen then continued to strip off her swimsuit.

The first thing that caught my eye was a full, dark bush of pubic hair, and then her well-cushioned curvy ass. Holy fuck, I wanted to sink my hands into those luscious cheeks. Gretchen twisted and turned in the mirror, checking herself out while I watched while hidden in the corner of my office. My hand found its way to my hardening cock and I unconsciously began stroking it ever so slowly.

I told myself it was wrong to be spying on my youthful neighbor, but that didn't stop me from watching her. Gretchen ran her hands over her body and inserted a finger into her pussy and began to move it around. She then bent over in front of the mirror. I saw her full ass and got an obstructed view of her pussy lips in the reflection.

Gretchen turned around and pulled out a vibrator from her dresser drawer. There was no way I was going to stop watching her now. I stared out the window as she laid down on the bed and spread her legs wide. I thought I could see her pussy glistening from the light in her room as she slowly inserted the vibrator.

As Gretchen fucked herself with the vibrator, she rubbed her nipples with her free hand. I began to stroke myself faster, in time with the insertion of her vibrator. I couldn't help but wish it was my dick inside of her instead of the plastic sex toy. I wanted to kiss her, suck on her nipples, lick her pussy, and fuck her. I fantasized about how tight her inexperienced pussy would feel as I plunged myself into her. In my masturbatory fantasy, she was also thinking about how I would ravage her young body.

When her hips began to wiggle and her free hand drifted down to massage her clit, I knew she was close to orgasm. I was stroking myself faster now, on the verge of cumming too. I saw her body stiffen and her face grimace in pleasure. Her orgasm rippled through her body as I began to cum along with her.

My cum filled the inside of my damp swim trunks as I watched Gretchen bring herself to another quick orgasm before she laid still with the vibrator still inserted inside of her. She rested for a few moments and then left the room. I assumed she went to take a shower, so I did the same.

When I was done showering, I returned to my office to see Gretchen dressed in a long-sleeved T-shirt and no bra. She wore loose sleep shorts and turned out the lights. I fell asleep that night to the nasty thoughts of what I'd like to do with my young neighbor.

Whenever I was in my office or even walking by, I would glance out the window, hoping to catch another glimpse of Gretchen in various states of undress or masturbation. Much to my disappointment, all I saw was a drawn shade.

That made me wonder, "Did she see me watching her?" The hopeful side of me wondered, "Did she leave her shade raised on purpose in the hope that I would see her naked?"

I hadn't seen Gretchen for a couple of days because we were both busy, but on the third day, I sent her a text that read, "Hey, I'm going to get the grill started. I've got some burgers ready to throw on the grill. Let me know if you're interested."

A few minutes later, she responded by saying, "Sounds good. I'll bring a salad."

"Great. Wear your swimsuit, too. I'll be in the pool."

"I was planning on it."

Several minutes later, I heard Gretchen opening the gate to the yard. She was wearing a T-shirt and shorts and carrying a bowl of salad. She took the liberty of putting the salad in an outdoor fridge I had on the patio and then proceeded to take off her outer clothing. I was pleasantly surprised to see her wearing a modest bikini. It showed just a hint of cleavage and a bit of her meaty ass cheeks. The top was a strapless bandeau type.

"Is that a new bikini?" I inquired.

"Yes. I decided to take your advice and try to wear something more fashionable. Do you like it?"

"Yeah, you look great."

I watched as she applied suntan lotion onto her nubile body. Her skin glistened in the sunlight from the lotion. I marvelled at how good she looked and wondered why she kept herself covered up all these years. I guess it's normal for young women to have body image issues, which is a shame.

Gretchen then said, "I got a little sunburn the other day, so I have to be careful. Would you put some lotion on my back, please?"

"Of course I will."

I was hoping she would ask. I squirted some lotion onto Gretchen's back and slowly rubbed it into her soft skin in a circular motion. I accidentally put too much on her, so it took longer to rub it in, but she didn't seem to mind.

"Um, that feels good."

"I've been told I give great back massages," I said as I pressed my fingers deeper into her neck and shoulders.

"Oh god, you sure do. Don't stop."

After the lotion was sufficiently rubbed in, I stopped massaging Gretchen's back, mostly because I was afraid I wouldn't be able to control my urges. My dick was beginning to grow and I didn't want to embarrass myself or her.

When I was done, Gretchen turned around, gave me a sheepish look, and said, "Thank you."

I stupidly replied, "It was my pleasure," then I quickly corrected myself, "I meant, I didn't want you to get sunburned. I'm happy to help out."

Gretchen snickered and replied, "I understand."

In all reality, it was my pleasure. It felt good to touch her young body and to hear her soft sighs of pleasure. I wanted to go further, but knew I couldn't and shouldn't.

I poured us both a glass of wine, and we enjoyed the warm water of the pool for almost an hour. We were in the deep end when we got out of the pool, and I followed Gretchen up the ladder. Her pillowy butt was practically in my face, tiny beads of water were cascading over her cheeks and down her legs. Her bikini bottoms were pulled into the crack of her ass. I was tempted to nibble on her cheeks. I walked behind her until we got to the table where the towels were. Her ass twitched and jiggled with each step. She did not attempt to pull her bikini bottoms out of her ass crack until after she dried herself. Gretchen must have known I was checking her out.

Gretchen didn't cover herself with a towel while I was grilling the burgers or during dinner. I told her I like a beer with my burgers and I stared at her curvaceous ass while bent over getting a couple of cans out of the fridge. I wanted so desperately to walk up behind her, pull her bikini bottoms down, and fuck her right there on the patio but we all know a guy can't act on all of his sexual desires.

Besides, what would she want with an old guy like me anyway? I'm old enough to be her father. That didn't keep me from looking and hoping, though. Maybe she thought it was safe to experiment with her more revealing bikini around me. A guy can always dream about being with a younger woman.