Deb got the invitation back in October to her high school reunion and we debated whether to go or not. I encouraged her to attend just to see what everyone else was up to in their lives. The event was in Pennsylvania, where she went to school, so I made flight and hotel reservations near the event center.  I had been with her to a previous reunion, and it was ho-hum. Lots of the girls attended, but a much smaller number of guys. We couldn’t wait to get out of there, so I assumed this would be the same way.

Boy, was I wrong!

We arrived at our hotel and checked in on the morning of the event. I had encouraged Deb to wear something tight and sexy so was looking forward to seeing her choice. We stopped and grabbed some wine on the way to the hotel, and I uncorked a bottle after we settled in to enjoy the pre-reunion. Deb went to get ready and I was very surprised when she walked out in a tight black dress with a deep cut in front that showed her cleavage!  I just said, “Wow!” as she modeled her attire.

Deb told me a friend had texted her that Matt was attending this year. Matt was an old high school flame that she was serious with for about three years before he left her and moved away. I had heard her talk about him and their relationship but knew she hadn’t seen him in many years. She told me she thought she’d show him what he missed, and I chuckled thinking about what that encounter would be like.

 I asked Deb, “So what if you see him and he’s still hot and in shape and gives you lots of attention?”

“I am sure he’s thirty pounds overweight and bald!” Deb said laughing, ”and anyway, he’s probably married and hasn’t thought about me in decades!”

I told her, “Don’t write him off so quickly…I would be hot for you after all these years if I saw you in that dress!”

We arrived at the banquet hall and I followed her around while she saw old friends, introduced me to classmates, and had a drink or two. Deb had kept up with me on drinks, so she was talkative and touchy due to the alcohol. We were standing talking to her best friend from high school when a tall guy walked up to us and said,” Hi there, it’s been a while.”

So, this was Matt – he was about six feet tall and in very good shape. He had a mustache and a full head of hair; the exact opposite of what Deb had expected. I could tell she was a bit taken aback as she said hello and hugged him quickly. I excused myself as it felt a little awkward, and went to find a restroom while they chatted. I returned to find them standing by the bar alone talking quite closely and having a drink.

I grabbed another drink, joined them, and chatted Matt up to get his story. He was a good guy, owned his own business, had been married for 20 years but had gotten divorced, and was focusing on his health and staying in shape by running in marathons a couple of times a year. I noticed that when he was talking Deb’s eyes wandered up and down his physique, and started to think about how this could become an exciting encounter

The reunion was coming to an end, and I suggested to Matt that he follow us over to our hotel, where we could chat some more and have a drink at the hotel bar.  He looked at Deb, and she quickly said, “Sure! I haven’t seen you in years! Let’s go!” 

I knew from that response she had her interest piqued and was feeling no pain.

 On the drive back over to the hotel, I asked Deb what she thought about Matt. She said, “Well he has matured quite a bit and seems to be in a good place.”

“Ok, but do you feel any old yearnings or feelings for him?” I asked.

Deb replied, “Well, it does remind me of some old days and just seeing his mannerisms is familiar – plus he has kept himself in excellent shape!”

I asked, “So was he any good in bed?” playing with her a bit to see what her response would be.

Surprisingly she answered, “Actually, he was pretty good! He had stamina that would go forever, and I recall his tongue was skilled!” 

I laughed and said, “Well maybe you should see if he still has it,” as we arrived at the hotel. Deb rolled her eyes at me as we got out of the car. Matt pulled in right behind us, and we all walked into the hotel bar.

I excused myself to find a restroom and told them to grab a drink and get comfortable in the bar. I purposefully took my time as I wanted to see how they would “connect” in this new setting. I slipped out of the restroom and caught a look at them at the bar – she was sitting close to him on a couch. They were laughing about something, and Deb lightly slapped his leg over something he was saying to her. I would have loved to stand there and watch this play out, but I went over to join them.

We all had several drinks in us, and I was listening to Deb and Matt talk about some old times that we laughed quite a bit over. Matt told us about his marriage and divorce, and that his ex-wife was frigid and didn’t like sex at all.

Deb quickly exclaimed, “Well I know you weren’t happy with that!!” before realizing the implication and turning red.

Matt laughed and replied,” Well, it was a big part of why we split.” I decided to push that a bit with a question.

“It sounds like you two had quite the sex life based on that exchange!” and laughed. I could see Deb look at Matt and then Matt surprisingly said, “Deb was always willing to try anything, and I regret leaving when I did.” 

Deb put her hand on Matt's arm and rubbed it telling him that was sweet, and I then asked the big question.

“Matt, it’s getting late – let's go up our room for a nightcap, and then we can call it a night.”

Deb looked at Matt with a hopeful look and Matt said, “Sure, I can relax over another drink.”

He offered to pay the bill, and while he was at the bar settling the tab I leaned over to Deb and said, “If you’re up to it, I’m fine with you seeing if Matt still has it when we get upstairs.” 

Deb turned and looked at me and I expected her to downplay it and tell me no, but she kissed me and said, “You sure you’d be ok watching me with my old lover?”  I just nodded and kissed her back, and I knew I was going to get a show.

We got into the elevator to go to our room, and Deb and Matt walked in first. I walked in and used our key to access our floor and Deb was up against Matt kissing him before I could even get the elevator door closed! Matt was a bit flustered and looked at me and I told him, “Up to you, my friend. Looks like she wants to reminisce some more!”

He smiled and lowered his mouth to deeply kiss Deb, and they made out like kids on the ride up.

We reached our floor and the door opened. Deb grabbed Doug’s hand and led him to our room. Once we got inside, Deb excused herself to go to the bathroom and Matt and I were standing there alone in the room.

I could tell he was a little uneasy and I told him, “Matt, Deb, and I have played quite a bit over the years so you’re not the first time. I’ll sit over here and watch and take a few pictures and you can have her any way she will let you.”

Matt thanked me and told me he’d be respectful, and I just chuckled while I opened another bottle of wine for us all.

Deb came out of the bathroom with her dress on, but it was obvious she had taken off her bra and I assume she didn’t have on any underwear. She took a glass of wine and sat on the end of the bed. Matt and I were still standing with our glass of wine, and Deb patted the bed next to her and told Matt to get comfortable. That was all the invitation he needed, and he sat next to her while we chatted.

He told us he had been active sexually with another woman for several years, but that it had ended about 6 months ago. Deb asked if he was seeing anyone right now, and Matt laughed saying, “My right hand has been my date since then!”  We all laughed at that, and Deb put her hand on his leg saying, “Sounds to me like you probably have some built-up tension!” 

As she said this, her hand slid up his leg to his crotch, where it was obvious he already had an erection.

Matt leaned over to kiss Deb, and she gave him a peck but said, “Lie back and relax – let’s see if I still remember how to get you going.” 

They both put their glasses on the table, and I sat back with my wine to enjoy what was about to occur.

Deb climbed on top of Matt, straddling his waist, and sitting on top of his hard cock. She leaned over and kissed neck and ear lightly while running her hands through his hair. Matt moved his hands to her hips and was massaging them when Deb sat up, slid her dress up, and pulled it over her head. There she sat naked on top of him, her 36D breasts displaying incredibly hard nipples that showed how excited she was.

Matt just said, “Wow!” while his hands reached up to grab her breasts and massage them. She grabbed one of his hands and pulled it up to her mouth, where she licked and sucked his fingers suggestively. He kept his hand near her mouth while she reached down and began unbuttoning his shirt. Once off, Deb rubbed and tweaked Matt's nipples then lowered her head and began licking and sucking on them (this drives me crazy!).

Matt pulled her head up to him and began to kiss her again and she rolled off him saying,” If I’m going to be naked you are too!” and unbuttoned his slacks and lowered them so he could kick them up. She left his underwear on, but it was obvious he had a long and very erect cock inside. She went back to licking his nipples while her hand found his manhood and began massaging it through his underwear.

Deb started to kiss down his stomach as she said, “You have kept yourself in good shape – I can’t believe you don’t have women beating down your door!”  About that time, she got to his underwear and she stopped, just looking at his erect penis as she rubbed it through the material.

“I don’t think I am going to last very long!” Matt told her. “This wasn’t what I had expected today, and it’s been quite a while. Plus seeing you and your body has got me about to explode!.”

“Just relax and take a few deep breaths – we’re in no rush,” Deb told him while she looked at me and smiled. She slowly rolled the top of his underwear band down, exposing his very large head.

“Wow, I had forgotten how large you are,” she told him. I have about 6 ½ inches but am very thick, while Matt appeared to have a skinny but very long cock. She pulled the underwear down his shaft and gently enclosed it with her palm. I could hear Matt give an audible gasp as she did that and she began to fondle and slowly slide her hand up and down what looked like 8 inches of hard dick.

Matt had his eyes closed and I could tell he was having difficulty controlling himself. Deb stopped and pulled his underwear the rest of the way off and they were now both fully naked on the bed. To give him a chance to recover Deb got up and came over to me, where she kissed me deeply bending slightly forward so Matt had a great view of her ass and her pussy lips from behind.  I massaged her hanging breasts and told her to go easy on him, and she giggled.

Deb stood up and went back over to Matt and said to him, “I remember you always liked it best when I rode you cowgirl,” as she climbed back on the bed.

Matt had recovered and told her, “I always liked watching your breasts bounce while you rode me, but first I want a taste of that sweet pussy!”  He pulled her down next to him, rolled over above her, and kissed down her neck to her erect nipples. Matt sucked on them both and Deb moaned as he did it, running her hands through his hair.

Matt kissed down her stomach and his fingers had already found her very wet hole. He slowly moved his fingers in and out of her while his tongue moved closer to her moistness. She had her legs wide apart at this point, and it was obvious he found her clit with his tongue when she jerked and arched herself up to meet him. Matt worked up and down her engorged pussy, stopping to lick and suck on her clit and Deb was moaning in ecstasy. He picked up his pace and began tonguing her faster and rubbing her with his thumb and quickly she raised her hips and began shuddering with a very forceful orgasm.

Matt laid Deb down on the bed to let her catch her breath. He was also breathing heavily, and I knew the best was yet to come. I asked them both if they would like a drink, and they both asked for water. Deb looked at Matt, and without any words between them lowered her head into Matt’s lap and began licking his semi-erect cock.

Matt laid back again on the bed while Deb positioned herself on the floor in front of him as I sat behind her. She slowly reached up and took his cock in her mouth and sucked loudly on his head. As she was doing this she caressed his balls, running her tongue up and down his shaft. She was looking up at him and started fucking him with her mouth, sliding his long dick in and out with more urgency. I could see Matt start to tense up as she continued to take him deeper in her throat. After a minute or two, he couldn’t hold back, and I saw him release his load into her mouth. Deb let it slip out of her mouth while she continued to slowly suck him as he came down. She used her tongue to slowly tease the head.

They were both spent, and it was late so they both got dressed and we sat and finished our drinks. Matt told us he had meetings the next day, and we agreed to meet up again in the next few months at our house. 

I’m looking forward to that visit to see what is in store for our next chapter with the high school boyfriend!