Lost Love And Anal Play

Five years ago:

I was 23 at the time and as always in very good shape. I never had a problem getting attention from girls however my usual circle of hookups was getting stale. My next door neighbor, Trish, and I have always been best friends, but that's where it ended. She was five years younger than me and I always made sure to look out for her best interests. She had a beautiful lean body and a cute face that one day would become the immediate fantasy of any man that lay eyes on her.

Whenever our families would get together we always ended up spending all of our time with each other. Our families were there, but as for us, we were the only two people that mattered. Clearly we had a mutual attraction, but I tried very hard not to think of her in a sexual way. We had known each other for too long and our friendship was too great. We always had "moments" growing up. For instance, in my pool we'd go swimming late night and I would end up rubbing her back under the stars talking about anything and everything that came to our minds. I'd always let my hands wander freely during those nights however that's as far as it ever got. Finally the day before she was heading off to her freshman year of college our "moment" became sexual, very sexual. For just that one time I acted on my desires.

We were on my pool patio as both our parents were away at work. Trish and I were soaking up the August rays as anyone would. Trish decided to take a quick dip to cool herself off. On the way to the pool something happened and she slipped. Her back struck right on the side of the pool and she fell into the water crying. Without missing a beat, I jumped in and lifted her out. I felt awful, she was crying into my shoulder when I saw the huge black and blue mark already forming on her back.

I gently placed her facedown on a towel and told her I'd be right back with some lotion. When I returned she was still whimpering. I gave her a comforting kiss on the cheek and a shoulder rub trying to relax her. Once she calmed down a bit, I proceeded to put lotion on the bruise. She closed her eyes surely hoping to forget how much pain she was in.

I never stopped rubbing her back. I asked her if she was ok, and she nodded her head in approval. I took more lotion and started giving her a lower back massage with my hands warily venturing to her bikini bottoms. I watched carefully for any sign that I should stop. She gave me none.

My hand dipped inside her bikini bottom and my fingertips slowly massaged a once forbidden area intently waiting for a signal of any kind. Trish turned her head and let a little moan escape.

"Did I just hear that or imagine it?" I thought to myself.

Intrigued, I let my index finger dip further below and touch the beginning part of her ass crack. I stopped for a second allowing herself to consider what was happening. I noticed her breath became shallow and I could feel her heart racing.

I continued to lightly trace my finger further down. Trish was surrendering herself to me completely. I delicately pulled down her bikini bottoms to reveal her gorgeous bottom. She parted her legs giving me better access. With my hands still slick, I started to rub her globes. I grabbed a cheek in each of my hands and gently spread them exposing her asshole. I couldn't help myself. I took my middle finger and gradually worked my way down her crack to her anus.

I was paying special attention to how she reacted to my finger advances. Just as I was about to reach her anal ring she took in a sudden shallow gasp of air and held onto it. We both paused for just an instant. As my finger then moved directly on her anus she finally let her breath escape. I just lingered there for a moment letting her, letting me get used to the situation. Next I pushed my fingertip inside. She willingly raised her ass higher taking more of my finger in her butt.

Her body took over at the point.

My hand stayed still and she moved back and forth repeatedly engulfing my finger with her anus. This lasted for a while. With my finger buried deep inside her ass I lowered my face. I took out my finger and started to slowly tongue her ass crack. Every second I inched closer to her asshole her breathes became more intense. As my tongue reached her anus she let out an incredible moan that made my body tremble in excitement.

Between her pants Trish managed to say, "This is so fucking dirty, you have no idea how horny it's making me".

I then made my tongue stiff and broke the plane of her ring. I worked my tongue in and out penetrating her further each time.

"Your tongue is so far up my ass, this fucking feels amazing!!!!"

Trish hardly ever said a bad word and hearing her say this almost made me blow my load right there.

When I felt her pussy she was so fucking wet. I immediately slid two fingers in her vagina. She grabbed a hold of my wrist driving my fingers in as deep as possible. I got the hint and forcefully kept my fingers deep and moving inside of her. Just as she locked onto her clit her entire body went STIFF! Every muscle went tense and she was succumbing to multiple waves of pleasure. Trish had just had the most powerful orgasm I had ever seen. Her body afterwards went completely limp.

I turned her over and we locked into an embrace. We fell asleep in each other arms for the rest of the afternoon. I felt like saying I loved her, but choose to remain silent.

Hours later our parents both came home and the afternoon moment was lost. Her back was surely sore but I thought that may have been the last thing on her mind.

She was obviously busy packing that night and thus left early that next morning. Trish never said bye to me. I thought that was really strange. She would never just leave and not say bye regardless of how early she left. I tried to put it out of my mind and figured we'd be in touch in the next few days.

I never heard anything.

I was crushed. I couldn't understand how something so intense could just manifest itself into nothing.

I tried to speak to her many times. Finally fed up with her silence I realized Trish had become a different person towards me. A man could only try for so long. I swallowed my pride and my feelings and just let her be. I was glad to remember that day, but sad to think I had lost a friend.

I was a different person instantly from that point forward. Things didn't seem as good anymore. New relationships didn't seem as powerful. I knew I had my heart broken.

Present Day:

As time went on, I slowly recovered from my mental despair. Later on that year I moved to a different state. And I learned to love again. I found a new girlfriend and my life was good. I had to admit thoughts of Trish came back from time to time, but I became quite good at pushing them back down until other thoughts entered my mind. I was happy and I had moved on.

I was getting the itch to move back home, and as luck would have it, work had an opening near my hometown. Although I had to leave my girlfriend behind for a few months I jumped at the chance. She understood and planned to move in with me once she had the same opportunity with her work.

A few months after being back it was early June. I was eating dinner at my parent's house and my mother mentioned to me that Trish just graduated college this year and would be moving back home any day.

"Great, just fucking great" I thought to myself.

For some reason I immediately started regretting the decision to move back here.

"GET A HOLD OF YOURSELF!!" I snapped. I've already dealt with these feelings. Things are different now and I've accepted this. Reminding myself this calmed me down. Soon other thoughts entered my head and I fell asleep on my parents couch like I had many times before.

When I woke up I heard some commotion coming from next door.

Fuck me! Trish was home.

I wondered how I should approach the situation. I could just stay inside and ignore it completely or I could actually go outside and say hi to her. However I knew if I said hi to her, how she reacted to me could make or break my night. Against my better judgment I went outside.

The second I saw her, I was awestruck. Her body was just as I had fanatisized. Her proportions were perfect. Her chest had filled out and her ass had definition that I never remembered seeing five years ago. And still not an ounce of fat anywhere on her body.

I opened the front door and tried to say something. Nothing came out. I tried to recollect myself, but I couldn't. I just stood there. I stood there with a stupid look on my face.

As Trish closed the car trunk, she inevitably turned my way and immediately did a double take. To my amazement and horrid disbelief she then turned back like I didn't even exist and went into her house.

What the fuck was that?!

She definitely wasn't the same Trish I had once known. Five years ago she would have run over and thrown her arms around me. Now she wouldn't even acknowledge my existence. Part of me had braced myself for that moment. Though the impact was still felt, I was able to shake the event from my head. And this time had a finality of "it's just the way it's going to be".

I returned to the couch where I had just finished my nap and started to watch TV. I noticed the reflection on the screen and realized I could see Trish next door unpacking in her room.

For some reason I couldn't help but think I was going to get lucky and catch a glimpse of her changing. Just as I was imagining what her body looked like naked again, I saw her looking in my direction through the window in her room. She had no idea I could see her. She had stopped cold in her tracks. She seemed to be chasing some memory in her head. Only when her father entered the room did she break her blank stare.

A couple of weeks went by since that night and I had become extremely busy at work. I did what I had been accustomed to doing and buried the event inside my head and rarely gave it another thought.

I was lying in bed one night when I heard a knock. It was midnight thus I didn't register that someone was outside my house. Again, this time the knocking was a little louder.

Heading to the door, I figured it was my girlfriend Katie coming down to surprise me since it was Friday night and she had the weekend off.

As I opened the door I started to say, "HEY KA....."

I couldn't believe it. It was Trish!!

"What the hell are you doing here?" I said kind of angrily.

She tried to say something but her words became choked up.

Trying again and fighting back her tears she managed to say "I asked your mother where you were living".

I understood. I threw my arms around her and we touched for the first time in five years. Neither of us could hold onto our emotions and we cried into each other arms.

After what seemed like forever we reluctantly broke our embrace.

"My mother says you have a girlfriend, I'm also in a relationship. I have so many things I want to say. I am, was, and still am so angry at you. Five fucking years, I am still mad at you. I hated you and I'm trying very hard to still hate you"

I was in shock, all these years went by and not one time did I imagine this was how she felt. She apparently saw the hurt and confused look in my face and so she started.....

"Growing up you treated me like I was the only thing that mattered in your life. You made my days brighter, you made nights peaceful, you made me feel safe. I was head over heels in love with you. I would have given myself to you anytime you wanted. ANYTIME YOU WANTED! That day you rescued me in the pool, that incredible moment afterwards needed to happen months if not years earlier. I waited so long for that to happen. Why did you wait until the last day before I went away? I cried that entire night knowing things would not and could not be the same. We were going to be 2000 miles apart. I became deeply depressed. Everything made me think of you. Finally enough was enough. I had to put you out of my mind completely. It was the hardest thing for me to do, but it was the only thing for me to do. The other day when I saw you standing outside your parent's front door, I felt everything again as if it was yesterday. All these thoughts I had buried down deep inside of me resurfaced. My heart aches. But now too much time has passed between us, things are different and we both have our separate lives"

With that last line, she turned and was gone. I didn't even get a chance to say anything. Eitherway, I doubt I could have even thought of anything to say. I didn't sleep at all that night, I only thought of the countless days and nights Trish and I had spent together long ago. Sooner or later night became day and I made myself get up and go through the motions.

There came a point during that next day where I knew I had to try. I had to try one last time to get back what was once mine. I was shaking as I dialed Trish's number. As her phone started ringing I could hear a ringtone nearby. It was coming from outside my front door. Confused I went to look outside and I saw Trish standing on my steps.

As I opened the door, she rushed in, put her arms around me and squeezed me tightly.

I was about to say something but she put her lips to my ear and said, "Shhhhh, just listen. Over the years I swore to myself I would never think of you. I slipped. I slipped often. Every time I was with another guy I would imagine that afternoon we had. How you handled me, how you took care of me and those things you did to me and I wished I could have that again. It was never the same, never like it was when I was with you."

When she finished talking, our lips met in a very slow and passionate kiss. Our tongues were deep in each others mouths. We kissed as two lovers rediscovering each other after years apart. I picked Trish up and brought her into my bed. We both undressed and our two naked bodies were glued onto one another.

"I've been waiting for this day my whole life, please make me yours again" Trish panted.

She took my dick in her hand and guided me to the entrance of her pussy. She was extremely wet and incredibly tight. I worked my dick all the way inside her while pinning her legs behind her head.

Trish pulled my body tightly into hers. I fucked her as hard and as deep as I possibly could. She was moaning into my ear the entire time. I brought a hand under her and started squeezing her ass. She was so wet that her juices liberally coated her ass crack. I started to play with her asshole. Trish loved this. She grabbed my hand and eagerly pushed my finger in her ass. Once I had one finger up her butt, she asked for another.

I always wondered if she had been just caught up in the moment five years ago or if she enjoyed her ass being toyed with. I needed no more confirmation. Trish was very sensitive back there.

I had two fingers in her ass and I was pumping her in and out when I felt her body turn rigid. She squeezed me incredibly tight and screamed.

Just as she squeezed me I knew I couldn't last any longer. I came the exact moment she came. I don't think I've ever shot such a huge load into someone before. Afterwards we both just laid there enjoying the moment. It took fives years, but we both knew this was meant to happen. Just like before, we fell asleep in each other arms. I was at peace with myself more than I could ever remember.

I awoke hours later to Trish playing with my balls. My cock was standing straight up. "Good evening sleepy head" she said. "I was hoping you'd wake up soon!"

"I'm up and you've got my attention now, you've made me rock hard" I said.

"I have to tell you something about me" Trish says "I've always gotten off from my ass being played with. Even before I went to college I always masturbated with something in my ass and something in my pussy at the same time. It's just the way I get off. Every time I feel your fingers or tongue on my asshole I can't help but become extremely wet and horny. So right now just sit back. I want to you to enjoy this. You're the only guy I want to be with and I want to make you feel the way I do."

I'll be completely honest, hearing her say this almost made me come in anticipation.

Trish worked her way under the covers and grabbed a hold of my cock near the base. She started licking the shaft up and down getting it very slick. She spread my legs open to get better access to my ball sac. Trish sucked on one ball and then the other. Using her saliva as lubrication she started stroking my cock. I felt her tongue go a little lower to the area just under my balls a few times. She was testing my reaction. Without saying anything I opened my legs further hopefully giving her permission to continue. She took the hint as I felt her mouth leave my balls completely and continue her journey further down.

I put my hands under my knees and held them upwards so she could have all the access she needed. As I hoped, Trish continually crept lower. I let out a gasp as her tongue reached my anus. She lightly rimmed around the edge. Taking her hand off my cock she brought them to my ass cheeks. She spread my ass open and drove her tongue in as far as she could. Much like I did to her five years earlier she poked her tongue in and out penetrating me further each time. The feeling of her tongue in my ass was incredible. And she was enjoying it as much as me.

I reached down to my own cock and started to stroke myself but Trish stopped me. She wanted to do everything herself. What was I going to say? I was in ecstasy. I put my hands on the back of her head and closed my eyes as her tongue continued working my asshole.

When her tongue left my ass she replaced it with her finger. She started to massage my prostate. I couldn't hold out much longer and told her so. She immediately started sucking my dick in anticipation of the load I was about to release.

AHHHHHHH!

I shot load after load into her mouth. She wasn't able to take it all at first. After swallowing what she could, Trish eagerly licked up what was left over. She came up and gave me a deep passionate kiss. Our tongues met fiercely as she shared what was left in her mouth. The whole moment was so incredibly kinky. I couldn't help but think what a lucky man I was.

I whispered into her ear that I loved her and have always loved her. We both knew our lives would never be spent apart again.

Needless to say, each of our "relationships" didn't last much longer than that next day. Our sex life is never dull, she is the most open and nonjudgmental person I know. Whatever I want and whatever she wants we both indulge to the fullest.

We both share a bond that will never be broken!