A love once lost was found again.

Like most high school sweethearts, Gail and I had dreams and plans. We would go to the same college, settle down, get married, and have kids. 

Things just didn’t work out that way. 

For a start, we were approved for different colleges. Of course, we pledged to stay together and continue our relationship and we did that for several months. But, little by little, the calls and texts dwindled to a few — then none. Despite wanting it to work, our deepest fears were realised and our relationship fell apart. Time and distance seemed to change everything and so our lives and careers went in different directions. 

For years after our parting, I lived somewhat on the wild side and came to recognize that it would take a special woman to develop a lasting relationship with me and share what I enjoyed.

Saying I was rather wild is putting it mildly. For instance, in a bar close to my office almost everyone knew me and I went out with just about all the women regulars in there. But they were nothing to me other than a succession of one night stands in which I satisfied my sexual urges and whims. 


One Friday, an office colleague asked if I wanted to have a drink with him after work at a relatively new bar. I hadn’t visited the place and I said, “Sure, Joe,“ and off we went. It was certainly different from my regular haunt. People of all ages, all types, were in there and they mixed easily: friendly people. 

As we were finishing our second drinks, I was surprised to hear my name being called. “Jim? Is that you, Jim?”

I didn’t expect anyone to know me in there but the voice sounded familiar and I turned around. I was stunned but somehow got to my feet. “Gail… oh my, I can’t believe it. Gail, how in the hell are you?” 

I opened my arms and we embraced, a big hug crossing over the years.

“It’s been so long. How are you? What are you up to these days?” Taking a quick breath, I said, ”Crap, sorry… where are my manners? Gail, this is Joe.” I nodded at my drinking partner. “Joe, this is Gail. We were sweethearts in high school and for a short time in college.”

“I’ve been good,” Gail was saying and I kept one arm around her, afraid she would disappear, run away or something. Damn, she was beautiful, even prettier than I remembered. My mind was all over the place but one thought dominated: Why in the world did I let go of her?

“Please, have a seat. Or are you with someone? I mean, do you need to rush off?” 

I was flustered, panicking really, and Gail offered a knowing grin. “No, I’m here alone,” she said, sitting and placing her wine glass on the table. “I often have a drink before going home. This is a really nice place to relax and let your hair down.”

I guess it was obvious that we had much to talk about because Joe politely made an excuse to leave. I was grateful and, as he walked away, I turned to Gail. “So, where have you been? I assumed you’d left town since we lost contact. Do you still live here? I’m sorry, I’m not giving you time to answer, am I?”

Gail grinned again, a twinkle in her eye. “Well, I finished with a Masters degree and landed a job at Noble and Noble, the law firm. I’ve been there ever since graduation.“

“That’s awesome. Congratulations.“

“Thank you. And yourself, Jim… what have you been up to?”

I took a deep breath, considering what to reveal. Do I tell her that I indulge myself in the wild side of life? Or should I keep that little tidbit to myself?

When we’d dated, Gail was very straight, almost reserved. Okay, eventually we played around and even had sex a few times. But it was always the same way: me on top while she lay back, legs open. Nothing spectacular or exciting, at least not for me. Gail had been a virgin and didn’t really know how to satisfy a man. I was young, randy, and wanted more, wanted to experiment, wanted to try different positions. Truthfully, I was quite selfish and hankered after more than Gail was ready to give, or could give. It caused problems and, in my view, contributed to the end of our relationship. But I didn’t realize what I’d got till it was gone.

“Jim, Jim, you still here? Seems you’re drifting off.“

“Oh, sorry.” I chuckled and shook my head. “My mind kinda slipped back to when you and I were… well, you know, together. Remember those days?”

“Hmm, of course I remember… how could I forget?” She stared into my eyes for a few seconds, then suddenly blinked and shook her head. “Anyway, I asked where life has taken you? You married? Kids?”

“Oh, Lord no. I’ve not found anyone who would put up with me.” I glanced away. The truth had suddenly hit me in the face: I’d never got over Gail. “What about you? Boyfriend, married, kids? All those things we dreamed of and talked about, have you found them?”

“No, that dream slipped away from me.”

‘Oh? Why’s that?” I moved closer and felt the heat coming from her. Surely, she could feel my heat, too. I still wanted her. In fact, I wanted her just as badly as I did back then. Probably even more.

Our gazes locked again — and I knew we still cared for each other. The need for each other was still alive. Why had I let her get away from me that night?

Grasping her shoulders, I turned Gail towards me and took the plunge. “I still love you,” I said. “I’ve never forgotten, never let you go. You’ve always been with me, inside me.”

Leaning in, I found her lips, the lips I’d unwittingly longed for over such a long time. Her taste and softness hadn’t changed, her smell was still the same. My love for her surged again, only stronger. Why did I let her go over something that’s… well, is it really that important?

Pulling back, I looked into her eyes. “Do you still feel the same, Gail? I know this is all a bit quick.” I paused then raced on, “Is there a chance for us to try again? I don’t want to lose you again.”

Gail pressed her lips together before answering. “Oh dear… yes, Jim, it is very quick for such talk. I’m truly not sure. ” She reached for my hands and in a soft tone said, “You must know that you hurt me terribly. Do you remember what really caused us to break up?”

As I looked into her eyes and gripped her hands, memories of that painful night came roaring back. That night had haunted me for years and I’d fought so hard to get over that one particular, special desire. Yet, it was still something that prayed on my mind, something that I’d always wanted to share with Gail if only she would let me. It’s something I truly enjoyed and I thought she could, too, if only she wasn’t so scared. It can be something so special between two people.

“Yes, Gail, I certainly do remember.” I looked down at the bar’s patterned carpet. I couldn’t look at Gail knowing that I hadn’t changed, that I still needed to satisfy this persistent passion in my life.

We talked for a while longer but shoved aside the one topic we desperately needed to tackle if we were going to rekindle our relationship. I took Gail home and said goodnight at the door. As much as I wanted to spend the night, I couldn’t — not while we had to work out this difficulty between us. If we couldn’t, if Gail wasn’t willing or able to share this experience with me, I would have to give her up. Yes, I knew without doubt that it really was such a strong and a vital part of my life. On the other hand, could I give it up and avoid losing Gail again? 

Trying to sleep that night was virtually impossible. I kept thinking about whether I could give up something that I enjoyed more than anything else, something that had become a major part of me. Yet, I loved Gail — definitely knew that now — and there was a possibility she could be back in my life. I didn’t want to lose her again…


Before I’d said goodnight on her doorstep, we’d arrange to meet again the next night, our first real date in many years. I wanted everything to be perfect. 

We had splendid food, fine wine and good conversation. We had time to really catch up but still we avoided the true cause of our break up like the plague. It was clear that neither of us wanted to risk anything spoiling the evening.

When it was time to leave the restaurant, Gail surprised and delighted me by suggesting I spend the night with her. Although it had been years ago, the last time we’d shared a night had ended in disaster. Gail had run off in tears — and that was the last I saw of her until we met in the bar.

So, no way would I mess up this time. I knew what Gail liked and I wanted her to have it all. Make her feel loved like never before. 

We took time to enjoy each other’s body and I made love to her tenderly and with heartfelt passion. As I licked and lapped, her pussy opened like a flower and I sucked the jewel waiting just inside. I looked up and saw her eyes tightly closed, her fingers grasping the bed sheets till they turned white. Then her mouth opened and ecstatic screams rose from deep within her belly as juices flooded my face. I drank eagerly, as though I hadn’t drunk in months. I couldn’t waste a drop of the beautiful nectar. 

Gail had a sweet taste and I continued licking and sucking her swollen clit even though she gasped and begged me to stop. Deep down, I knew she needed more. Her thighs, no longer taut and clamped around my head, eased apart, allowing me full access to her beautiful desirable pussy. Her lips opened like pink rose petals while her hips moved up and down pushing her pussy at my mouth. Her moans became louder, her fingers tangled in my hair, and I felt Gail was close to coming like never before. 

I raised her legs, spread them wide, and she bucked one last time before releasing a scream from the pit of her stomach. She’d lost all control, her body writhing frantically, unlike anything I’d known all those years ago. Amazing!

When Gail calmed, gradually relaxing back into the crumpled sheets, I released her clit and gently lowered her legs. I moved up her warm body to kiss her mouth with passion and desire. At that moment, I’d never loved anyone as deeply as I did Gail.

The night had been totally for her. Oh yes, I’d yearned to touch her perfect rear hole, but I knew better. Above all, I desperately wanted to show Gail how much I loved her — and how sorry I was for being so selfish in the past. 


Waking in Gail’s arms was the best feeling I’d had in a very long time. Well, since Gail had left me. All the other women I’d shared a bed with since then were just that — women, casual sex partners and no more.

Suddenly, Gail stirred and, before I could say “Good morning,” she slid down the bed and slipped my cock into her mouth. I thought she’d swallowed every inch of me as she slowly moved her head up and down, her tongue circling my hardening shaft. Licking from the tip of my cock to my balls, she took my balls in her mouth, sucking one then the other while stroking my cock to full erection. Fingertips then spread drops of pre-cum over my head and I put my hands on her head.

She had me so excited I hardly knew what was happening before I felt a finger pushing into my ass. Gail immediately brought her mouth back to my cock, tightened her lips around it — and gave one last push with her finger. I instantly shot a load like never before, filling Gail’s mouth with spurt after spurt. She kept swallowing, her finger lodged in my ass , until my balls were drained. 

I was breathing heavily as Gail licked my cock clean before sliding back up the bed. She softly pressed her lips against mine then looked into my eyes. “ I never want to lose you again,” she whispered. 

I held her close. “ Never again Gail,” I sighed.

We still needed to talk about what caused our break up — but not now, not today. Instead, we decided to stay indoors and just enjoy each other, indulge in our reunion. First, though, we headed for a shower. 

With a washcloth, I went over every part of her wonderfully soft body. When Gail’s back was against a wall, I scooped her up and lowered her onto my throbbing cock. Deep inside her moist pussy, I felt Gail squeezing me while she rocked up and down. In reply, I thrust into her, striving to fill her tunnel. I wanted her so badly, I was like a madman.

We clutched each other tightly as our passion headed for release and, miraculously, we came together, gasping and grunting while rope after rope of my cream combined with her juices to flood her pussy. 

Eventually, I noticed the water was running cooler and I set her down. Wrapping her in a towel, I carried her back to bed where we cuddled before I got up to fix some brunch. Walking out of the bedroom, I looked back to make sure I wasn’t dreaming. 

In the kitchen, with a few minutes to myself, I pondered again on that terrible night when Gail ran out of my house swearing never to see me again. She’d called me names, even said I needed help. In the depths of my reminiscing, I felt hands on my waist and heard the sexiest voice say, “Come fuck me, baby.”

As I began to turn, Gail untied my robe and, as it slithered to the floor, she took a pace backward. A gorgeous angel with an hour-glass figure stood in front of me, nipples standing proudly on voluptuous breasts, beads of nectar clinging to a clean-shaven pussy. Beautiful lips sang my name, “Jim, come to me, baby.” 

As I stepped toward her, Gail turned and leaned over the kitchen table. I went with it, trailing wet kisses from her neck along her spine. Hands on her shoulders, I turned her around. I wanted to look at her, look into the depths of her brown eyes, and let her know how much I loved her. But, apparently, Gail had one objective in mind and she again turned and lay on the table.

Watching her spread her legs, I spotted a tube of lube by her side on the table. She must have brought it down with her but my mind was in a whirl, I was in a daze. What was she thinking? Was this a trick? Or a test? Surely not. Gail wouldn’t do such things. But what had changed her? Changed her mind? Did I dare? The last time I tried to enter her ass, Gail left me.

“Gail, are you sure,” I whispered in her ear. “We both know what happened the last time I tried.”

Gail raised her ass. “Are you gonna keep talking,” she said, spreading her long legs even wider, “or are you gonna fuck me?” 

How could I resist?

Slipping a hand between her legs, I found her clit was already enlarged. And she was wet, more than wet: juices flowed like a river. I began to massage her slit and her hips moved with each movement I made, her ass raising ever higher.

“Please, Jim, I need you,” she groaned. “Do it now.” 

Somehow keeping calm and controlled, trying not to rush this longed-for moment, I continued to stroke her open flower while I rubbed a finger softly over her brown hole that was waiting for my cock. 

Having coated my fingers with the lube, I eased inside — just a little, not all at once. This had to be something that Gail would remember as enjoyable and sensational not hurtful or painful. Continuing to massage her clit, I aimed to keep her totally aroused while I prepared her for my cock.

Pushing a finger slowly into her anus, I gradually went deeper, opening her precious tight bud to receive me. When I felt she was ready, I stroked her pussy and got into position, poised to penetrate her back entrance. 

Whispering, I again asked, “Are you sure?” 

I didn’t want to lose the love of my life again and, suddenly, at the very point when I was about to quench my desire, enjoy what was so imperative to me — the very act that had driven us apart — it was no longer important. All I wanted was to love Gail and have her in my life. Having my cock in her ass no longer meant anything.

I stepped away, then reached for Gail’s hands and told her to stand up. Gail frowned, clearly puzzled and unable to understand why I’d stopped. She was offering me what I’d always wanted… till today. I had to tell her how I felt.

I explained that I now felt stupid, knew that it was ridiculous that I’d let something like the desire for anal fucking to tear us apart. The years that had been lost, wasted, were all because of my selfishness. 

“Gail, all I want is you. I want a second chance to complete our dreams, get married, have our children. All this other stuff…” I waved my hands, “that’s not what I want. I want you and our dreams.


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Copyright © Copyright for Simplicity 2019. All rights reserved. This work may not be copied, transmitted, published in any other form, or used in any other way, without the author’s express written permission. Please don’t steal my work, And redo it as your own.

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