A reunion long time coming

Diane and I met in high school and have remained friends for over 40 years now.

While we never officially dated, we were pioneers in the “friends with benefits” category, though neither of us would “hook up” with each other if one was seeing someone else steady. We definitely did our share of sexual exploration but also we connected on many other levels, and that allowed our friendship to grow and prosper over time.

After high school, we went off to college and eventually each found steady relationships with other people, married and moved away from our hometown and each other. Despite the distances, and much to the trepidation of our respective spouses, the friendship endured. First by letters, cards, and phone calls, then later by using emails and texting. We maintained a close relationship for all these years based on mutual respect and a unique insight into each other.

In the relationship, there was nothing that the other could not share. We were probably closer in some respects to each other than we were to our own spouses. Over the years we shared good news and bad, joy and sorrow. We saw each other on occasion when a return to the hometown area was made. Usually based upon a funeral or the occasional high school reunion.

Texting between us has become a common occurrence. We connect several times a week. Almost always it was the mundane gripe about work, weather, occasional politics or news about a mutual acquaintance. Additionally, what was never a subject of our texts was any trashing, complaining or otherwise bad mouthing our spouses.

Although there was never any overt “sexting” or sharing risque photos, there was often a theme to the texts where snarky comments, double entendres, inside jokes and dark humor were shared. Underlying these exchanges, a subtle little ember of “what if” could be detected from both of us.

I often thought, “What if we found ourselves single again? What if we had a little too much to drink when we next saw each other? What if we actually did become a couple and marry all those years ago?”

Can you have a “best friend” of the opposite sex and not have it be with sexual undertones? I believe the answer is yes. But the real question is, can you be best friends with a member of the opposite sex whom you did have sex with and not have there be sexual undertones in the friendship? That is nearly impossible to accomplish, at least in our relationship.

So, where does this all bring us to? It brings us to the 40th class reunion that’s where. Reunion plans were made and Diane flew in from the other coast to attend. I lived in the same state as our old school but away from the old neighborhood.

Ever since Diane told me she was coming into town, my mind was racing. In all actuality, this will very likely be the last time we would physically be together. With retirement approaching and families scattering, roots will be pulled up and distances made greater.

While my mind switched through different scenarios, I had no idea what Diane was thinking. Did she have the same inclinations? How far was she willing to go?

In the past, when we met, there was never more that a kiss between us. Neither would have any regrets nor feel any remorse when we returned to our spouses.

But what about this time?

When the time came for the reunion, I made plans to pick Diane up at the airport.

I met her in baggage claim; we exchanged a hug and a light kiss and headed off to the parking lot. A little chitchat was had on the way to the car. I placed her luggage in the trunk and opened her door for her.

“Still a gentleman,” quipped Diane.

“At times,” I returned.

Looking at me with a raised eyebrow, she said, “I hope to see one of the times when you’re not, soon!”

Well I guess that answered my question of what she was thinking about this reunion. I entered the car and as soon as I closed my door, Diane leaned over and gave me a big deep kiss. It was a soft, yet passionate kiss and as our tongues intertwined, my cock hardened and I was transported back to a time when we would be doing this at a drive-in movie theater.

“It has been a long time since we did that!” Diane said, as she broke off the kiss.

“It sure has been,” I returned.

As I adjusted myself to get in a comfortable position to drive, Diane latched her seat belt. She was wearing oversized comfort clothes for the plane ride and as the shoulder belt traced between her breasts, it became obvious she was not wearing a bra as her nipples formed two small points on her shirt. As I looked at her, I noticed that her breasts were larger than they were in high school.

As I pulled away from the lot, Diane reached over and grabbed my crotch.

“Someone’s happy to see me,” she said. “And I am glad to know I can still do that to you after all these years, especially at your age,” she added.

“Still a prick tease aren’t you, and you shouldn’t start something that you can’t finish,” I responded.

“Just shut up and drive.” she returned.

The drive to her hotel was about an hour and for the first part we caught up on each other’s lives. We discussed our jobs, children, children’s jobs and of course some snark about who would be attending the reunion. Social media takes a lot of the guessing out of what people look like now days. Of course, during the drive I was glancing over checking her out. Even forty years later, she still looked good.

When all the preliminaries were out of the way, the ride got quite. The only sound was some road noise and the 70’s station playing on satellite radio. There has been something that I wanted to say to her for years now and this lull seemed like the perfect opportunity.

Glancing over to Diane, I said,” There is something that has bothered me for a long time that I would like to talk to you about.” This piqued her curiosity, and she looked over at me, giving me her full attention.

I continued, “When we first met and became intimate, we were young and inexperienced. As time has gone by, I realized that I was not the best sexual partner. I really did not know about, nor did I really care about, how to please a woman. Don’t get me wrong, we did some crazy sexual stuff and it was fun, but I never really focused on your pleasure. If I only knew then what I know now, I would have carried myself differently. I had a poor understanding of the female anatomy and how to ensure that you were satisfied during our sexual encounters. For that I apologize. Some day, I would like to make up to you my shortcomings. I think I owe you a few orgasms.”

The look on Diane’s face was priceless. She was not expecting me to say something like that. Her mouth was open slightly, her eyes directly focused on me. I was able to detect that her breathing had quickened just a bit. She licked her lips and turned away slightly.

Diane responded, “Yes we were young and inexperienced but it wasn’t as bad as you think. The sex was always pleasurable for me. It wasn’t like a porn movie where the girl is having repetitive screaming orgasms, but that’s all fake anyway. I am sure I wasn’t always the best sexual partner either. I bet we have both learned a few things over the years that make us better lovers. Jack, I appreciate your honesty. If there was anyone that I knew would mature into being more concerned with their partners pleasure it would be you. And yes, you do owe me a few orgasms!”

She finished what she had to say just as I arrived at her hotel. “How about a little something to eat and a cocktail to celebrate us,” I said, as I turned off the engine.

“I need a shower before we even think of doing anything,” she said.

Yes there was some innuendo added to what both of us said. “Where is this going?” I though to myself. We have both said things that opened up many possibilities. Was this just part of our usual banter or was this the start of something else?

I grabbed her bag from the trunk as she checked into the hotel. Following her to the elevator, I stepped in. We said nothing during the ride, but I continued to look at her body. Even in loose clothing, you could tell she maintained her self well. Her hair was nearly the same shade of red that it was 20 years ago. “She has a great colorist,” I thought to myself and something that I would never mention out loud.

We exited at her floor, found her room and went in. “Put the bag on the bed and rest while I shower,” She said. Opening her bag, she grabbed some toiletries and a small bag form it and headed off to the shower.

I sat in a chair gazing out the window as I listened to the water turn on. In my mind I could see her standing in the shower. The water flowing over her naked body as she soaped her breasts, her hands gliding down her body toward her pussy.

My cock hardened as my imagination was whirling in my head. “Where is this going to go tonight?” I thought, as I slowly rubbed my hard-on through my pants.

It was a quick shower and Diane cracked the door to let the steam out. I peered through the opening hoping to catch a glimpse of her naked body but the mirror was too steamed up.

Diane startled me as she exited the bathroom. She was wearing nothing but a lacey bra and a matching pair of boy shorts. My god, I wanted her. Right here, right now. She glanced over at me and smiled as she leaned forward to open her bag further to grab some clothing.

I could not take it any more. I walked over to her as she stood up. From behind, I placed my arms around her stomach and nuzzled her neck. The smell of her freshly showered skin was intoxicating. I stepped closer, my cock resting against her soft ass.

She must have felt how hard I was because she pushed back against it. I kissed her neck and gave it small nips as my hands traveled up to her breasts. As I was grasping each one, feeling their softness through the fabric of her bra, Diane pulled away slightly and turned to face me.

She placed her arms around my neck and our lips melded together again. A hungry, wet kiss ensued. We held each other’s faces in our hands as we shifted our weight from side to side.

Diane broke our kiss, stepped back, and started to undo the buttons on my shirt saying, “You my friend, are over dressed.”

I grabbed her hands and looked into her deep green eyes. “Di, are you sure you want to do that? We are on dangerous ground here but haven’t gone too far yet'” I said softly.

‘Jack,” she said in a low tone, “I have thought about me coming out here ever since I got the invitation to the reunion. What you said in the car on the ride over, I have to admit, made me hornier then I have been in years. We have always respected boundaries when we meet but I think that this is the last time we may be in a position to do something together. I think we owe it to ourselves to not let this moment pass without taking advantage of the opportunity. Will we regret this tomorrow, I don’t know. I do know, I will regret it if we don’t do it.”

I stood there just taking in what she said. We really are connected because I felt the same way. I kicked off my shoes as she continued to remove my shirt. Di stopped when all the buttons were opened. She reached over and pushed her bag off the bed. Then grabbed my shoulders and spun me around as I removed my shirt.

Diane undid my belt and pants as I stood there. As my pants fell to the floor, she pushed me back onto the bed. Still clad in her bra and shorts, Diane dropped to her knees. She looked up at me while pulling off my briefs, freeing my raging hard cock. They weren’t even past my knees when I felt her hot breath of my cock. She took its entire length into her mouth as her tongue swirled around on it.

I kicked my briefs the rest of the way off and laid back. Her hands rested on my thighs and slowly massaged them, moving slowly inward as her head bobbed up and down. Soon she grabbed my balls and caressed them as her tongue worked on my cock.

Forty years ago oral sex was not a regular part of our interludes for either one of us. When she did give me a blowjob, it was more of a hand job with a little bit of lips, and any attempt cum in her mouth was strictly forbidden. What she was doing to me now was a huge difference. There were no hands on my cock tonight. It was all mouth, lips and tongue and it felt amazing. I gazed down and ran my fingers through her hair.

I let out soft moans and started to thrust my hips to fuck her mouth as she bobbed in unison. “You feel amazing,” I said, as our eyes locked together. “If you keep this up I am going to cum.” With that she began to bobbed even faster with small rests where she twirled her tongue around the head of my cock.

I soon felt that familiar feeling deep inside as she brought me closer and closer to orgasm. I tapped her lightly on her head. “Diane,” I said, “I am going to cum right now.” As I said that, she gently squeezed my balls, brought her lips to just under the head of my cock and swirled her tongue around and around.

I gripped the sheets tightly, raised my hips and felt spasm after spasm of cum leave my cock and deposit itself in her mouth. I shook as her tongue traced my now super sensitive cock head, my breathing slowed and I relaxed. I don’t know if I ever felt as strong of an orgasm before in my life.

Diane released my cock, sat back on her legs and swallowed my load. “As you can see, I have acquired some new skills over the years,” said Diane, and continued with, “I wish I knew your cum tasted this good back when. I would have sucked you off every day.”

As I recovered from her amazing oral skills, I pulled her up onto the bed and we were now lying next to each other. I kissed her deeply, tasting the remains of my cum on her tongue. My hands moved to her breasts, kneading them through her bra, teasing the erect nipples by rolling them through my fingers.

I broke the kiss with her mouth and proceeded to kiss down her body till my mouth reached her tits. Pushing up the fabric of her bra, I took a nipple into my mouth, sucking on it while swirling my tongue on its hard tip. I alternated from tit to tit as Diane let out soft moans, running her hands through her hair.

Forty years ago it would have been a quick lick of the tit and move on but now, I was taking my time, using all my knowledge of erogenous zones. I did nothing else but focus on her breasts for about 10 minutes then slowly ran my hands down her chest, onto her belly and across her thighs. Taking my time, my fingers traced over her mound, her panties were sopping wet, and as they came to rest on top of her slit, I pressed down and began massaging her clit.

I massaged her clit as I continued to suck on her nipples. Tonight it was about pleasing her. I was taking my time and making up for all the times I did not focus on her pleasure.

Diane’s breathing hastened, her legs began to move back and forth and her pelvis was doing small gyrations. I continued to suck her tits and rub her clit, focusing on her and only her. A short time latter, she grabbed my hair with one hand and the sheet with the other. Her body became rigid, her breathing faster, her moans louder until she began to shudder. I didn’t let up at all, continuing to rub her clit as she came.

She pulled my hand away and tried to roll over to be on top of me. “Stop,” I said, “I owe you a few more orgasms.”

With that, I sat her up, removed her bra, then slid her soaked panties off her. I took a few seconds to remove my remaining clothes then slid down onto the floor. Kneeling against the bed, I pulled her hips over to me, gazing at her trimmed mound glistening with her juices. I pushed her thighs apart slightly and delved into her pussy with my tongue. I started at the bottom, licking each of her labia, nipping at them lightly with my teeth. I moved my tongue into her slit and probed deep into her. I kept fucking her with my tongue, occasionally stopping to flick her still sensitive clit.

I continued to address her with my mouth. As time passed, her clit was less sensitive and I began to focus on it more. Quick darts with the tip of my tongue alternating with firm pressure licks, my tongue flat against it.

I easily slid two fingers into her wet pussy, finding her G spot and flexed my fingers massaging it.

Soon, Diane’s legs closed in against my head, squeezing me as she had another orgasm. I felt her pussy contract against my fingers, her hips bounced against my tongue. She let out a small scream and pushed my head away and whispered, “Stop, I need a break. “

I rose up, swung her back fully onto the bed and lied down next to her. I kissed her again, this time sharing her taste with her. Our hands caressed each other all over and she eventually found her way back to my cock, now fully recovered and ready to go again.

She pulled back and said, “Man, have you learned a few things too over the years. Where was that tongue when we were young?”

We continued kissing and caressing until, Diane stopped and said,” I want you in me now, I need you in me now. I want you to fuck me like you have never fucked me before.”

That’s all the encouragement I needed. I rolled her onto her back, positioned my yearning cock against her wet pussy and felt it easily slip in. I reached down and raised her legs, placing them over my shoulder. Leaning forward onto my outstretched arms, I started slow deep thrusts into her pussy. I could feel her muscles gripping down on my cock.

I began to increase the speed of my thrusts as Diane rose up to meet me. We were in perfect sync with our rhythm. We stared into each other’s eyes, not a word being spoken.

I could feel that she was nearing another orgasm but not quite there yet, she needed something a little bit more to get there. I stopped stroking, pulled my cock out of her and rolled her onto her stomach. She immediately got up on all fours as I moved in behind her.

“You remember my favorite position,” She said.

‘Its easy to remember, since it is mine too,” I replied.

I grabbed her hips and thrust my cock into her waiting pussy. I started slow but quickly increased the pace of my thrusts. Soon the whole bed was moving. I leaned back for a little more leverage and a better angle to see her breasts swaying to and fro as we fucked. I knew she was getting close to cumming again but for some reason, I was still not there yet.

Diane shifted her weight slightly then reached back with one of her hands, grabbing and squeezing my balls. Her hand stayed there for just a moment then moved up to her clit, stroking it as I fucked her. That’s what both of us needed. Her moans increased and I felt the pressure building again at the base of my cock.

She rubbed her clit faster as I thrusted faster. We were in a frenzy of moans, and gyrations. Sweat forming on both our bodies. It only took a few more minutes till we both reached our plateaus at the same time. Her hand dropped to the bed. My hips convulsing as I felt my cum being deposited deep into her.

We both stopped moving and held still, my cock still in her, as our breathing slowed.

I collapsed down onto her, pushing her flat onto the bed, then rolled off her, staring at the ceiling. Her arm reached across my chest as we looked at one another, our panting slowing.

She finally spoke, “Wow, I guess sex is like fine wine, it gets better with age. I don’t think I have ever felt so sexually satisfied as I do now.”

“Well then,” I responded, “I guess I accomplished my mission.”

We moved closer together, entering into a warm embrace. I looked at her as she closed her eyes. “Yes you have,” was all she said as she drifted off to sleep in my arms.