03

After Gretchen went back to school, I found myself missing her more than I expected. I knew that because of the age difference, there was no way we were ever going to have any type of lasting relationship. However, I missed her companionship and the awesome sex. What 50ish man wouldn't miss fucking a sexy twenty one year old? Reliving being a sexual mentor for her became my main fantasy while masturbating. I longed to feel her soft lips wrapped around my cock, or to fuck her tight pussy, and ass.

I didn't bother Gretchen while she was at school. However, my heart beat a little faster when I got a text message from her a couple of weeks later.

"Hey, how are you doing? Sorry, I haven't messaged you, but school's been crazy. I miss you."

"No need to apologize, I understand. I miss you, too."

"My vibrator has been working overtime. I needed new batteries. LOL."

"My hand is getting a workout, too," I replied.

Another time, I got a text from Gretchen that read, "I'm using my vibrator right now thinking about you."

"Send me a picture."

I wasn't sure she would comply with my request but a minute later my phone buzzed with a picture of her vibrator inserted into her pussy. I went to the bedroom to start jerking off.

Gretchen then sent this message, "Send me a picture of your cock," so I returned the favor with a picture of my hard dick with a drop of precum on the tip.

I then got a request to video chat from Gretchen, which I quickly accepted. I was treated to a live shot of her masturbating. She must have had her phone propped up on the nightstand of her room, so I followed suit.

"I'm so horny, Ray. I wish you were here to take care of it for me."

"I wish I were there too, Gretchen. I'd eat your pussy and then give you a good hard fucking."

"I want to suck your dick again and ride it while you suck on my tits. I can't wait to fuck you again, Ray."

"I can't wait to fuck you either."

Our video chat went on for several minutes while we mutually masturbated. I watched as Gretchen feverishly worked over her pussy and clit while telling me how much she wanted to fuck me again. Damn, that was nice to hear and great for a middle-aged guy's ego. She kept telling all the things she missed about what we did during the summer while bringing herself to two orgasms.

When she was done, she gave me a close up of her swollen pussy and said, "This pussy is yours, Ray."

That made me cum, and I shot my load all over my stomach and told her, "This cum is for you, honey. My dick is all yours and it'll be right here waiting for you when you come home again."

We had several more mutual masturbation sessions over the next few weeks. We started using our laptops to video chat so we could take advantage of the larger screens. We could only chat when we were free, but it was pretty exciting for us. I had a personal webcam model who would pose and masturbate for me. She'd give me close up views of her tits and shake them for me or she'd spread her legs and pussy lips while inserting her fingers or vibrator. She really turned up the temperature one evening when she bent over and stuck her vibrator up her ass.

"I bet you wish it was your cock up my ass, don't you, Ray?"

"Oh, honey, you know I want to fuck that gorgeous ass of yours again. You're such a cocktease, Gretchen."

"I told you before that I'm not a cocktease because I fully intend on pleasing you."

One time, she let me watch while she shaved her pussy which led me to say, "I like a little bit of bush, so just trim it up real nice for me."

She followed my instructions, left a landing strip of hair, and said, "It's just for you, Ray."

Gretchen got off on the fact that an older man was jerking off to her naked boy while telling her how sexy she was. It was good for her ego, too.

Now that Gretchen was dressing differently and showing more confidence in herself, she was gaining the attention of the guys on campus. She would tell me when she was going on a date. I think she was trying to see if I would be jealous.

I said to her, "I told you guys like a confident woman. You're young, you should date guys closer to your age."

Gretchen would let me know how her dates went, and I'd give her some advice on how to deal with men. I was a sexual mentor and relationship advisor to her. I have to admit, part of me was jealous, but I was also realistic in knowing she should find someone younger to date and establish a relationship with.

One night while we were chatting, Gretchen informed me, "I've gone on a few dates with Brad, and I think he wants to have sex with me."

"Oh, I'm sure he does. It's only normal for people to want to have sex. Do you like him, and is it something you want to do?"

"I do like him and I'm pretty horny, as you know."

"LOL. Oh, I know. Well, give it a shot and see how he is in bed."

"I'm afraid he won't be as good as you, Ray."

"There's only one way to find out, Gretchen."

"I guess you're right. If I do, I'll tell you all about it. We're going out on Friday night."

"Wear something sexy but not slutty. Let's video chat on Friday, and I'll help you pick out your outfit."

"Ok."

Late on Friday afternoon, Gretchen and I started a video chat, and she told me she had narrowed it down to three outfits to pick from for her date. She said they were going out to dinner and drinks afterward. She was wearing a black bra and red bikini panties as she held up the outfits.

I told her, "First thing, if you think you might be having sex with Brad tonight, you need to wear matching underwear."

I went on to say, "You have to model the outfits for me."

She went to her dresser and changed in front of the camera. Gretchen was now wearing a white lace half bra and matching thong. I found it strangely exciting to be helping her pick out her attire so she could fuck someone else that night.

The first outfit was a pair of tight jeans and a simple tank top, and I commented, "Naw, that's something you wear out with your parents."

The next choice was a conservative dress that came down to her knees, and I said, "No way, put that one away."

The last choice was a very short jean skirt and a semi-sheer button-down white blouse, and I said, "That's the one, but you have to leave some of the buttons undone.".

"But you can see my bra through the blouse, and he'll see plenty of cleavage."

"Oh my goodness, Gretchen. Haven't you learned anything this summer?" I joked, "That's the whole point. If things are going good and you are open to sleeping with him, then you unbutton more of the blouse. That will signal to Brad that you want him to make a move on you."

"Oh, all right."

"Trust me, Gretchen. I'm a guy. I know what I'm talking about. Make sure you give him some peeks up your skirt, you know, make it look accidental."

"You mean like I did with you."

"Exactly, just like that."

That was the first time Gretchen admitted to giving me some upskirt views on purpose.

Before we ended our chat, Gretchen told me, "I'm a little nervous. What if he doesn't want to sleep with me or doesn't like my body?"

I scoffed at that idea by saying, "He wouldn't be going out with you if he didn't like you. No normal guy is going to turn down an opportunity to have sex with a beautiful lady like you. If he doesn't, it's his loss. You're darn good in bed, and I'm speaking from personal experience. Let me know how it goes."

"I will."

I felt some anxiety for the rest of the night. I felt like I had released a baby bird into the wild after nurturing it until it could fly on its own. I wrestled with the feelings of jealousy and pride that I was able to give a nerdy girl confidence in herself. I wanted to be the one fucking her that night but I knew she had to live her own life. I kept thinking about Gretchen as I was in the hot tub with a beer, watching a ballgame on TV. I wasn't sure when or if she would tell me about her date, so after the game, I got ready for bed.

It wasn't until almost noon on Saturday that I received a text from Gretchen that read, "Brad just left. Let me know when we can talk."

"Call me anytime."

A few seconds later, Gretchen called me, and as soon as I answered, she said, "Well, we did it."

"I guess I don't have to ask how it went."

"We had sex last night and again this morning."

"That's great. How was it?"

"To be honest, you are a much better lover, but it was still good. I was so fucking horny."

"I could have told you I was better," I said with a chuckle.

"Yeah, you're much better at oral sex. He seemed to like my blow jobs."

"I told you that you were good at it."

"I'm still pretty horny, too."

"Why don't we have a video chat on our laptops, and you can tell me all about it?"

"You're so bad, Ray."

"That shouldn't surprise you, Gretchen."

I took my laptop into my bedroom and waited for her to start the chat. Gretchen was wearing a bra and panties, and I was in my boxer briefs when we started the chat. I was already semi-erect when she began to tell me about her date with Brad.

They went to dinner at a casual restaurant close to her apartment and took my advice and gave him a peek up her skirt when she got into the car. Gretchen could tell he was also staring at her chest all through dinner. She was glad she chose to wear a half-bra underneath because it worked just like I said it would.

After dinner, they went to a place a block from Gretchen's apartment for a few drinks. She undid another button on her blouse while he was at the bar getting their drinks. After a couple of drinks, she invited him back to her apartment to hang out and have another drink. Before long, they were making out on the sofa. His hands were all over her body. He had her blouse and bra off and was playing with her breasts and sucking on her nipples.

That's when she took her bra off for me, and I stripped off my boxer briefs. I was already hard.

Gretchen went on to tell me how they moved into the bedroom, got naked, and she started to suck his dick. He was about the same size as me, but not as thick, so she was able to deep throat him with no problem. Brad kept telling her how good she was at blowing him.

After blowing him for several minutes, he laid her back and ate her pussy. He wasn't as good as me, but he was still okay. After she orgasmed, the fucked her in the missionary position.

Gretchen laid back, took off her panties, and spread her legs for me. She then inserted her vibrator into her pussy. I was slowly stroking my dick as she told me her story.

"You're a better lover, Ray, but it was still nice to have something other than my vibrator in me."

"I understand, dear. Tell me more."

"He didn't last as long as I expected but I still liked having a man cum inside me."

"We fell asleep after that and we fucked again this morning before he left."

"So, you only came once between last night and this morning?"

"Yeah, that's why I'm so horny now."

"You know I would have made you cum a few times by now."

"I know, Ray. That's one of the reasons I called you."

"I'm glad you did, honey. Now, I want you to cum for me."

"I want you to cum for me too, Ray."

We were both silent for a little while as we watched each other masturbate. I kept picturing her fucking Brad while also wishing I was there to satisfy her.

Just before she came, Gretchen said to me, "Do you want to hear something that I know you'll like?"

"Of course I do."

"When I was sucking Brad's dick or when he was fucking me, I was thinking of you, Ray. Just like I am now."

That was a huge boost to my pride, and I replied, "Oh fuck, Gretchen, what I wouldn't give to be there now. I have a huge load of cum built up in my balls that I'd love to shoot into your mouth or pussy."

Gretchen sped up the insertion of her vibrator, was furiously rubbing her clit, and began to say, "Oh fuck me, Ray. I want to feel you inside me. I want you to cum for me, Ray. Cum for me. OOOOOOOOHHHHHHH."

"Oh fuck, Gretchen, you're such a horny bitch," I replied and began to shoot cum all over my stomach while my hand stroked my cock.

"I can't wait until we can be together again, Ray."

"Me either, Gretchen."

Gretchen showed me the remnants of Brad's cum on her vibrator and around her pussy. I found it strangely exciting to know she fucked a younger man the night before and earlier that morning. I had turned her into a hot, sexy woman who loved sex, and she was in the process of further exploring her sexuality, all thanks to me.

It became a routine for Gretchen to call me before and after her dates. She would call me before a date with Brad, and I'd help her pick out something to wear. She'd then text me either late that night or early the next morning to tell me how it went. I looked forward to hearing about her sexcapades with her young lover.

It helped to hear about her fucking and sucking someone else while I was watching her masturbate too. While I still felt pangs of jealousy, I was also being rewarded with the sight of a naked young woman talking dirty to me while using a vibrator on herself, and telling me how much she missed fucking me while I jerked off too.

I had no right to expect a young woman more than half my age not to sleep with other men. I also had the promise of her wanting to fuck me when she came back for Thankgiving break. It built up the anticipation of being together again. It made me want her even more. We all have our fantasy women, but I had the good fortune to know that I was going to fuck mine again. I was counting down the days until she came home.

Finally, Thanksgiving was approaching, and Gretchen planned to come home for the long weekend. She would arrive late on Tuesday and leave on Sunday morning. It didn't leave us much time, especially with the holiday mixed in.

Gretchen told me, "I already told my parents that I asked you to help me with one of my final papers and my essay for grad school, seeing you're a professional writer."

"I'm more than happy to help you out, Gretchen."

"They're already done, silly. It's just an excuse for me to be at your house."

I wanted to ask about Brad, but I figured I'd leave it alone as long as Gretchen wanted to be with me over the long weekend. The anticipation of having sex with my young neighbor again was making me horny. I resisted jerking off because I wanted to save my jizz for her. Neither one of us knew exactly when we'd get together, but we knew it was inevitable.

I heard Gretchen's car pull into her parents' driveway about 9 PM on Tuesday. I knew it was too late for her to come over, besides, it would have made her parents suspicious if she came to see me immediately upon her return home.

About an hour after she got home, Gretchen sent me a text that read, "Hey, I'm home. I'm hoping we can get together sometime tomorrow."

"Welcome home, I don't have any plans, so let me know when you can make it."

"Sounds good. What are you doing for Thanksgiving?"

"I plan on eating junk food, drinking beer, and watching football all day."

"My parents want you to have dinner with us. It's their way of thanking you for helping me around the house last summer and with my papers. My brothers are out of the country for work, so they won't be coming."

"Gee, I don't know. I'm not sure if that's a good idea."

"It will keep them from becoming suspicious of, you know, what we do together."

"I'll think about it and let you know tomorrow."

"Okay, see you then."

I wasn't sure I could sit through dinner with Gretchen's parents when I was fucking their daughter behind their backs. I've seen them since, but just to say hello or wave to them as we were coming and going.

About half an hour later, I received a text from Gretchen saying, "Look out your office window."

I scampered as quickly as I could to look out my window, and I wasn't disappointed. Gretchen's bedroom window shade was up, and her lights were on. I never asked her if she had let me purposely watch her masturbate before, but now I knew for sure. I left a small light on that was on my desk so she knew I was watching.

While Gretchen didn't masturbate for me that night, I got a perfect view of her getting ready for bed. She pulled her t-shirt over her head, which revealed her black bra that encased those beautiful breasts that I craved.

She then ever so slowly unbuttoned and unzipped her jeans and peeled them down her legs, leaving her in her bra and black bikini panties. Her gorgeous butt cheeks peeked out from the bottom and sides of her panties. She walked around the room for a minute or so, and shook her fluffy ass at me.

Gretchen bent over with her ass facing the window and slowly peeled her panties off and down her legs. She then shook her bare ass for me again as her butt cheeks jiggled. She was looking over her shoulder, grinning at me. She spanked her ass a couple of times before standing up.

She turned around and removed her bra and bounced on her toes, making her breasts jiggle. Gretchen then pulled her pussy lips apart while flicking her finger against her clit.

I sent her a text that said, "You're being a cocktease again."

I saw her typing a return message on her phone that said, "We've been through this before. I'm not a tease if I fully intend to please."

She then inserted her finger into her pussy, which I was positive was soaking wet. She fingered herself a few times, and then brought her finger up to her mouth, and began to suck on it like she was giving a blow job.

I was fully erect and decided that two could play this game. I turned on the main light and did my own striptease. I stood in the light of my room and gave her a clear view of my naked body and hard cock.

I received a message from her that said, "Who's the tease now?"

"All's fair, honey. I'm not going to jerk off. I'm going to save this for you."

"I can't wait until you eat my pussy and fuck me. I'm so horny. I need a good fucking."

"My dick is here waiting for you."

The anticipation of being with Gretchen on the Wednesday before Thanksgiving had been building for months. I hadn't gotten laid in three months, and I knew I was hours away from ending that drought with a sexy young woman that I personally mentored, so I knew the sex would be outstanding.

I had a couple of dates with women close to my age during the interim, but both ladies had issues. I didn't feel the reward was worth the risk of getting caught up in their drama. The end result was that I had a serious case of blue balls that was going to be resolved that night.

On Wednesday, Gretchen said she was going shopping with her mom for most of the afternoon, and she could come over after dinner to "work on her papers." I told her I'd be ready for her whenever she got there.

Part of me was worried all day that Gretchen would tell me she couldn't make it because of some family obligation. I was thrilled when I got a text that she was on her way over. As soon as she walked in the door, she ran up to me and gave me a big hug and kiss.

"I missed you, Ray."

"I missed you, too, Gretchen. You have no idea how often I think about you."

I poured us both a glass of wine, and we sat on the sofa, catching up on our lives. There was no need to rush into things. I was stealing glances at a much more confident young lady who seemed to be even more self-assured now. I was a proud mentor.

Gretchen was modestly dressed, which I expected now that her parents were home, but she was still a lovely woman, and I told her so.

"That's what I like about you, Ray, you make me feel so good about myself."

"Well, you are beautiful. It just took you a while to realize it."

As we gazed into each other's eyes, I brushed a loose strand of hair away from her face, and ran my hand down her cheek, to her neck, and shoulder. I then leaned in to softly kiss her. That kiss led to another more passionate one as my hand drifted down to cup her breast through her bra, which caused Gretchen to emit a soft moan.