iMessage from Ashlyn St.. Pierre: hi

With one simple text message she had shattered the illusion that I could go the rest of my life without ever thinking about her again. I hadn't spoken to Ashlyn St.. Pierre in over five years, and it had honestly taken me almost that long to stop thinking about her... obsessing about her. I had, at long last, accepted the end of our three-year long relationship. She had been my only love and, truth be told, my only lover. And, like a shot out of the blue, she was back in my inbox.

iMessage sent by you: Yes?

I had agonized over my response to her text for the better part of a day. Should I ignore her message? Try to be friendly? Pretend I didn't recognize her number? The dozens of possibilities zoomed through my mind. However, each response that I considered made me seem either too eager to talk to her or entirely too bitter. I suppose that's what happens when the love of your life cheats on you, though.

iMessage from Ashlyn St. Pierre: how are u?

I felt my heart start to beat faster and faster... I had imagined this moment for years! The last time we had spoken (well, the last time we had texted) she had informed me in no uncertain terms that she never wanted to talk to me again. She had found herself a "real man" who was "sexually compatible" with her, and she just didn't want any contact with me anymore. She still cared about me, she insisted, but felt that having me in her life would put a strain on her new relationship. So, to ensure that I wouldn't disturb her and her new boyfriend, she had blocked me on everything; no texts, no instagram, no snapchat. Every phone call went straight to voicemail and every email was bounced back. She had completely cut me off for five years. I guess today she had finally decided to unblock me...

iMessage sent by you: I'm doing good. Been really busy with work. You?

It wasn't a complete lie... I had been really focused on my career for the past few years and it was finally starting to pay off! I had just recently managed to save up enough to put a down payment down on a beautiful townhouse. For years I had felt a pretty embarrassed about living at home with my folks but now, at twenty-eight years old, I was finally living on my own. Most of my friends had rented apartments with friends or with their significant others, and I remember feeling intensely jealous as I scrolled through Instagram looking at their Pinterest-worthy apartments photos. But now, a few years later, they were realizing that they had no savings and no ability to buy a home anytime soon. I finally felt like I had arrived at financial adulthood and I was enjoying living alone in a big two-story townhouse.

iMessage from Ashlyn St. Pierre: yeah, Sebastian and I are great
--

It took all of three texts for her to mention him! Sebastian Scott. Just thinking about him... them... still gave me a pit in my stomach. I guess that I had hoped that they would have grown apart over the years. Maybe I had hoped that he would have cheated on her the way she cheated on me. Maybe that's petty, but for years I had fantasized about her coming back to me. I had dreamed of her begging for my forgiveness, having been given a taste of her own medicine. But I had been kidding myself, of course.

I was lucky to have met Ashlyn during her 'ugly duckling" phase. I was a few years older and we worked together at a part-time summer job. I was a freshman in college, and she was still a junior in high school when he first met. She was cute, and silly, and shy. She was very pretty, of course, but I hadn't been immediately attracted to her. She certainly wasn't immediately attracted to me. She usually put her long brown hair back in a ponytail, dressed in loose-fitting clothes, and wore almost no makeup. Maybe that's exactly why I was able to be myself around her... Within weeks we had started dating. It was the first relationship for both of us. Soon I couldn’t imagine my life without her.

However, as we got older Ashlyn seemed to become more and more beautiful. And she completely transformed her appearance as she approached her freshman year of college. She dyed her mousy brown hair jet black and began visiting the salon regularly to keep it silky and shiny. She had gained a little weight over the years, but she wore it perfectly! Her chest slowly grew into perfect tear-drop shaped breasts that were large enough to fill up any top. She had begun working out regularly, building herself a thick peachy ass. Even her wardrobe changed: she was wearing more sun dresses and skin-tight yoga pants, and less baggy sweatshirts and old jeans. She began to put on more and more makeup, accentuating her tan features and soft freckles. And her piercing blue eyes could always melt me, even if she was now displaying them behind big stylish oversized glasses. In short, my girlfriend had blossomed into a thick, voluptuous beauty! But now she was way out of my league. As the years passed, I missed literally everything about her. Not just her incredible looks, but her laugh, her smile, the way she made me feel like I was the smartest person she had ever met... the list goes on and on

iMessage from Ashlyn St. Pierre: u there?

I hadn't responded yet... What was I supposed to say? I'm sure Sebastian was doing great. He was everything I wasn't! I was never someone who got a ton of attention from girls. I wasn't completely ugly or anything, but I just didn't ever seem to be one of the guys girls fawned over. I was tall but always pudgy from a lack of athletic activities. In high school I was nerdy, wore glasses, had bad acne, and spent most of my time playing saxophone in the marching band. I had plenty of friends that were girls, but never a real girlfriend until Ashlyn. And while she blossomed as we got older, I just never hit my stride. I slowly gained weight (at my heaviest I weighed 270 pounds spread out across my six-foot two-inch frame), battled adult acne, and found that my hairline was already receding before my twenty-second birthday. When we broke up I was twenty-three but the truth is that I looked like I was closer to forty-three. I had really tried losing weight and exercising regularly, but I just couldn't move the needle. And the more beautiful Ashlyn became, the more unattractive I felt. I knew that Ashlyn was getting more and more attention from guys around her college campus, and I couldn't help but feel incredibly uncomfortable when we would hold hands or kiss in public. I felt like everyone's eyes were on us because I just didn't look like I could possibly be her boyfriend. You would think that I would have felt proud to be with her, and I was! Incredibly so! And, as far as I was concerned our sex life was incredible too! I just felt, in my heart, that she could do better. And yet, I was stunned when she cheated.

iMessage sent by you: What do you want, Ash? I mean, last time I checked I was still blocked on all your social media

While Ashlyn had blocked me on every form of social media known to man, Sebastian hadn't. He wasn't a big social media person, but he did have an old Facebook Account that still had some of his pictures from college. I wish I could say that I didn't cyberstalk him but, honestly, I have to admit that I studied every inch of his public profile. He was basically to my age (maybe a year younger), came from a family of four brothers, was in some dumb frat in college, and was very good looking. I feel awkward saying that—I've never considered myself to be anything other than completely straight—but the truth is that he was a very attractive guy. He was the type of guy that high school girls dream about. He had classic good looks. From his Facebook pictures I could see that he had short shaggy brown hair that he liked to gel over, a dazzling white smile, and smooth tan skin. He wasn't tall—maybe five foot nine or so—but he had a very toned, athletic body. He wasn't massive, but I could tell that he went to the gym regularly. I think he played lacrosse in high school. His profile pictures were filled with photos of him at parties, campfires, and football games. He was clearly a guy who liked to have a good time. I doubt he had ever cracked open a book, though.
Fuck, I was angry at him! This macho frat bro had to have known that he was hooking up with a girl that had a long-term serious boyfriend. And, as far as I was concerned, we were serious… We talked about buying a house together and I was even starting to think about proposing the summer after I graduated. In my mind's eye he had always taken advantage of my naive young girlfriend and stolen her away from me. But I had to admit that I was also angry with myself... I was angry that I had let this perfect woman slip right through my fingers. And I think the worst part was that she was dating someone who was so completely different than me! Based on his profile I could tell that him and I would have had nothing in common. Except Ashlyn, of course.

iMessage from Ashlyn St. Pierre: that didn't stop you from trying to friend Sebastian on fb though, did it? :P

Fuck. I felt my cheeks growing red instantly. She was right, of course. I had "Friend Requested" him on Facebook a month or so after Ashlyn had blocked me. It was a moment of weakness, for sure. It's totally embarrassing now, but I honestly couldn't help it! The jealousy that I had felt post-break up was so intense and I was dying to know more about the guy who had stolen the love of my life. When she had broken up with me she hadn't really told me a lot of details about him... just that they had met at a party and clicked instantly. Naturally, he denied my friend request.

--

Our actual breakup was a pretty awful ordeal. I still have nightmares about it. Probably the worst part was that she couldn’t bring herself to actually tell me in person. She literally sent me a text telling me we were over. I was stunned and completely shocked. I just didn’t understand. After days of begging to see her, Ashlyn finally agreed to meet up with me so I could have some closure.

When she first told me about him she insisted that they had only made out. I was devastated and angry, and I wish I could say that I played it cool and accepted our breakup with dignity. But I did not. I balled my eyes out at two o'clock in the morning, in an empty parking lot no less, and begged for her to stay with me. I remember that she said, "I'm sorry Thomas, but I just don't think I'm the same person anymore…". I didn't understand and begged her to think about all that we had gone through together over the past three years. We were each other's first everything.

"I'm so, so sorry". She was kind and thoughtful, but firm. When the finality of our situation began to sink in, I demanded to know every detail of why we couldn't work through this. Sensibly, she refused to talk about it. "I don't want to hurt you..." I remember her saying, tears welling up in her eyes. But I pressed on. I needed to understand.

"Fine!" She relented. "The truth is that I've ... I've.... I've been having sex with someone else..." I was completely stunned and immediately sick to my stomach. How could she do this to me!? I just couldn't believe it. Stupid, right? "Who the fuck is he!?" I demanded, choking back tears.

She explained that he was someone she had met at a party, and when she first saw him—when he had first smiled at her— she just knew in her soul that they were going to fuck. They had been eying each other all night and she loved his shaggy brown hair, his fit build, and his cocky confidence... She said it was like animal instinct; she was drawn to him and just couldn't say no.

"Well, was he better at fucking than me?" I blurted out the question without thinking, feeling a mixture of revulsion, embarrassment, jealousy and shame wash over me.

"Thomas... I..." She wasn't a cruel person. She wasn't throwing any of this in my face or trying to make me jealous. Maybe had I been a little older or had a little more life experience I would have known to just walk away.

But I insisted on an answer. "Well!?"

"Yes" She answered flatly, looking down at the floor. But then, as if she couldn’t help herself, she blurted out "He's amazing...it's amazing. I had honestly had no idea sex could feel that good. I'd never... well..."

"What? Please, tell me..."

"... I guess I just didn't know what I was missing"

I couldn't believe what I was hearing. How could that be true? I thought we had a great sex life! Ashlyn was always horny and never had any complaints... She was always telling me how good I made her feel while she was riding me. This couldn’t be true!

"I don't understand..."

“well… I guess… I didn’t … ugh … know how good it could feel when… when someone… ughh… I'm really sorry Thomas, but the truth is that I just don't want to have sex with you anymore. It's as simple as that. I'm really sorry"

Telling her that I loved her, begging her to stay with me, insisting that I would try to improve myself, was no use. The conversation dragged on and I could tell that she was getting exhausted, both physically and emotionally. "Look, we're just NOT sexually compatible. You've only ever been with me... so you don't really know ... ummm... you just don’t know how to make me feel that Sebastian does. And I didn't realize until now because you were all I’ve ever known. But now that I've been with a real man... I'm sorry…"

There was nothing more to say… her mind was made up. She drove away and I remember balling my eyes out in the front seat of my car. But the real kick in the gut came the next morning. I noticed on Facebook that Ashlyn had changed her relationship status to "taken" with some guy named Sebastian Scott. Sebastian fucking Scott... his name was burned into my memory. The post had already been liked by a bunch of her friends—people I had known for years! I immediately looked him up on Facebook. I wish I never did...

--

iMessage from Ashlyn St. Pierre: thomas?

iMessage sent by you: Yeah...?

I answered, lamely. No one had called me Thomas in years; everybody just called me Tom. Even just seeing her type my name sent butterflies through my chest.

iMessage from Ashlyn St. Pierre: do u remember how u liked it when I would send you pics when we were dating?

iMessage sent by you: Uh, yeah…?

Suddenly my heart was racing. I couldn't understand why she would be texting me after all this time, let alone bringing up the intimate pictures we used to exchange while we were together. Truth be told, I always loved receiving pictures of my girlfriend and she always enjoyed sending them. I think she liked the attention… who wouldn't? We were young and in love. I would get cute little pics of her stretching at the gym or snaps of her in a cute dress all the time. I had saved many of them on my phone before she blocked me, but she insisted that I get rid of any leftover pictures after our breakup. She even demanded that I send a screenshot of my phone's Recently Deleted folder as proof. I did what she wanted and, because of that, I hadn't seen a picture of her in five years.

iMessage from Ashlyn St. Pierre: what would you do to see a new pic?

My heart stopped. What the fuck. Was she actually seducing me? Fuck fuck fuck! Could this really be happening? Yes! Maybe after all these years she was finally getting bored with Sebastian fucking Scott. I couldn't believe it! I had honestly never stopped loving her... is it possible that she felt the same? I had fantasized about this moment for years and it was finally happening!

iMessage from Ashlyn St. Pierre: venmo us fifty bucks and u can have one

Shit! The thrill, the excitement, and the anticipation that I was feeling immediately evaporated. Now I just felt intense anger and jealousy. Was she just fucking with me? Had she really unblocked me after five years just to screw with my head?

"What the fuck Ashlyn!" I couldn't believe that my girlfriend—sorry, ex-girlfriend—had unblocked me to tease me like this.

iMessage sent by you: Fuck off Ash

iMessage from Ashlyn St. Pierre: fine, be like that
I sat in silence for a moment, seething with anger. Then my Snapchat app chimed. I opened the app and my jaw dropped...
Ashlyn had messaged me a picture, but it was unlike any photo she had sent me when we were dating. Those pictures were cute, in an innocent kind of way. This was a picture of a full-grown woman... a woman that I hadn't seen in five years. Her long straight black hair cascaded onto her tan shoulders, her glossy pink lips were pursed at the camera, and her makeup had been done to accentuate her high cheekbones and stunning blue eyes. She was wrapped in a delicate red, sheer robe and tight red thigh-high stockings. Around her neck she wore a simple gold chain. But it was her incredible lingerie that really stunned me! The one piece set she had on was like nothing I had ever seen on her... she certainly never wore anything that sexy for me while we were dating! Her big, round breasts seemed to pour out of the sheer red bra, and tight red straps ran down her stomach and around her waist. The straps led down to small lacy red panties. She had become even more curvy over the years, and she exuded sex and sensuality. She was gazing into the camera with a slight smirk on her lips, holding open the red robe so that I could see her body. It was the type of lingerie picture you would find in a Victoria Secret Catalogue. She was stunning. And I immediately felt my growing dick straining against my jeans.

The stunning photo disappeared after ten seconds. I gasped as the picture vanished into snapchat oblivion. I felt dizzy and disoriented. I hadn't seen or spoke to Ashlyn in five years, and out of the blue she sends me THAT!? I couldn't believe it and I didn't understand what was happening.

iMessage from Ashlyn St. Pierre: hit us up if you change your mind

Fuck! She knew she had me... How could I resist that? I needed to see her again... needed to see her incredible tan body wrapped up in that beautiful red sheer robe. I gulped hard and typed out my message.

I replied, feeling lightheaded.

iMessage sent by you: What's your venmo?

iMessage from Ashlyn St. Pierre: Not mine. You need Sebastian’s. His account is SebtheStud93

“Fuck!” I actually said the word out loud. She wanted me to send HIM—the guy she cheated on me with—money for a sexy pic of her? What the fuck! It was so wrong. And yet, my dick was rock hard. I unfastened my belt and pulled out of my five-inch penis. I had never been self-conscious about my size until Ashlyn cheated. Ever since then I felt, well, inadequate. And it didn't help that my dick has a mild upward curve. I didn't realize that was a problem until Ashlyn revealed that Sebastian was such a superior lover. My hand slowly glided up and down my shaft as thoughts of Ashlyn in that red lingerie lingered in my mind. I knew how screwed up this entire situation was… I knew how insane it was that I was slowly stroking my dick to the thought of seeing pictures of another man's girlfriend, even if she was my ex-girlfriend. I knew I should just block her and get on with my life but I couldn't. I needed to see more.

iMessage sent by you: And I just venmo him fifty bucks?

iMessage from Ashlyn St. Pierre: yeah. But u need to write what it's for

iMessage sent by you: What?

iMessage from Ashlyn St. Pierre: on venmo you need to write what the money is for

iMessage sent by you: Ok. What do I write?

iMessage from Ashlyn St. Pierre: write can I please see another photo of your sexy young wife, sir

FUCK ME. My head was spinning. What the fuck? She actually wanted me to ask Sebastian for pictures of her? Wait! Did she say… his WIFE!? Oh my god! I couldn't fucking believe what I was reading. Ashlyn had just turned twenty-five a few months earlier... and she was already fucking married to him? And she wanted me to call him SIR? What the fuck... he was YOUNGER than me! I felt a strange mixture of lust and nauseous course through me as I reread her message over and over again. I had spent the last five years holding out hope that maybe one day she would reach out to me and we might get back together. I had deluded myself into believing that perhaps, once she was a little older and a little wiser, she might realize that our love was genuine. That dream—that silly fantasy—died in my heart as I read her message. It was a delusion, of course, but I had clung to it for years. Now the crushing reality entered my mind: Sebastian Scott had stolen my girlfriend and he had fucking married her. She was his, completely. And she would never be mine again.

Was I angry? Jealous? Fuck yes, of course I was. But I looked down and realized that I was still slowly gliding my hand up and down my five inch member. Shit, I realized that I was even more turned on than I had been before! I had to admit it: the thought of her being married to him—the thought of her now being Mrs. Ashlyn Scott—turned me on to no end. What the fuck. Why was the idea of Ashlyn being married to Sebastian making me so fucking horny??

iMessage from Ashlyn St. Pierre: ... well?

I hadn't responded yet. I was just sitting there staring at her text, massaging my dick. Of course she had married him! "He's amazing...it's amazing. I honestly had no idea it could feel that good" Her words from the night we broke up still echoed in my mind. Is it possible that she had only been with two men in her life: me and Sebastian? Was sex with me literally all she had to compare to sex with him? That thought made me even more jealous and even more horny. Fuck. Why was that turning me on so much!?

I couldn't do it… could I? I couldn't ask another man for intimate pictures of his wife… could I? The fact that I was even considering it was totally humiliating.

iMessage from Ashlyn St. Pierre: this offer expires in five minutes

Shit! I stood up and paced around the room. Was I really that desperate to see pics of my ex girlfriend—Sebastian's hot little wife? It really didn't help that I hadn't fucked anyone since Ashlyn... Pathetic, right? Talk about an epic dry spell. I had tried dating—I’d downloaded all the apps--but I just couldn’t really connect with anyone. Sure, I had a few matches and went on a few pleasant, albeit uneventful, dates. The girls were nice enough but in my mind they never quite measured up to my ex-girlfriend. And the girls that did turn me like Ashlyn had never matched up with me. Ashlyn was literally the only girl in the world for me. I couldn’t help feeling like she had ruined me somehow. Could I really allow this opportunity to slip past me? I gulped and prepared to swallow my pride. I opened the venmo app, set up a fifty-dollar transfer, and entered the message like she instructed.

iMessage sent by you: Can I please see another photo of your sexy young wife, sir?

I pressed send. I couldn't believe that I actually fucking did it. Fuck! I didn't even think about the money. What's fifty dollars, in the grand scheme of things… I figured that I could afford to throw away a little. A moment later, my phone lit up from a number I didn't recognize. I opened up the message and gasped out loud. My hand started working its way up and down my dick faster and faster. She looked incredible!

This time Ashlyn was standing with her side to the camera, looking over her tan shoulder with her big round ass on full display. Her long black hair hung down her back and stopped just above the back of her delicate red panties. The tight red straps wrapped around her middle, extenuating her amazing curves. I could see the smallest little red triangle wedged between her full, peachy ass. Her tan skin looked incredible and her breasts looked even large from this side angle. The delicate red sheer robe was wrapped around the top of her thighs, right under her ass, making it look even more incredible. On her wrist was an expensive gold watch and in her eyes was pure lust. She looked unbelieve. And I couldn't believe that I had just bought the picture from her husband!

iMessage from Ashlyn St. Pierre: like what u see, thomas?

iMessage sent by you: Yes

What more could I say? I was practically speechless.

iMessage from Ashlyn St. Pierre: u never got to see me in anything like that, huh?

iMessage sent by you: No

It was true. Even on her best day during our relationship, she had only looked half that stunning…

iMessage from Ashlyn St. Pierre: ready for another?

Saving the photo to my camera roll, I typed out a quick response

iMessage sent by you: What do I have to do?

iMessage from Ashlyn St. Pierre: This time say can I please see your hot young wife's tits, Mr. Scott? And it will be a hundred this time

I did as I was instructed, feeling my cheeks grow red even as my dick pulsed and throbbed. I didn't even think twice about the money.

iMessage sent by you: Can I please see your hot young wife's tits, Mr. Scott?

"Fuck" I moaned, as another pic appeared in my inbox. This time Ashlyn was standing directly in front of the camera. The delicate red sheer robe was gone, which allowed me to see every inch of her stunning torso unobstructed. She was insanely sexy! But what almost made me cum right then and there was her magnificent tits! Her right hand was resting gently on her collarbone, just above her right breast, but she didn't need to hold them up. Her tits stood in perfect position and her small nipples were rock hard. The top of the stunning red one-piece was hanging down from her shoulders, but she was still wearing the panties and the sheer stockings. Straps from her lingerie still ran down her stomach and wrapped around her waist. She had a seductive, mischievous smirk on her face, and she stared directly at the camera. It was almost like she was looking right at me. I could practically feel the cum building up in my balls.

iMessage from Ashlyn St. Pierre: do you miss getting to touch my tits, thomas?

iMessage sent by you: Yes

As I typed out the message I continued beating my dick up and down as I stared at her magnificent chest.

iMessage from Ashlyn St. Pierre: are u jealous that my husband gets to touch them whenever he wants?

"Shitt" I panted, as I saw her text message. Of course I was fucking jealous! I was more than jealous... I was obsessed! Why was she teasing me like this? Why was she throwing her sex life with her husband in my face? And why was the thought of them together turning me on so much…?

I typed back, feeling even more embarrassed than before.

iMessage sent by you: Fuck yes. I miss them so fucking much

iMessage from Ashlyn St. Pierre: haha

Her response only fueled my raging embarrassment. It was weird… it was like my arousal and my embarrassment were somehow connected. The more I thought about how she belonged to him, and how I was buying pictures of his hot wife from him, the hornier I became. I had never experienced anything like this.

iMessage from Ashlyn St. Pierre: are u jealous that my husband gets to feel my little mouth around his big dick every night

God! Up until today I had never really pictured them together. Sure, I had wondered what he must look like... wondered if he really was so much better in bed than I was. But I had never really allowed myself to imagine them fucking. I guess I knew it would drive me to distraction. But now I couldn't help picturing my ex-girlfriend blowing her boyfriend—sorry, her husband— giving head to her husband. I was so jealous it was unbelievable. Ashlyn hadn't really given me many blowjobs when we were together... I guess I always just assumed she was happier having sex. And now she was giving her husband head each night? Fuck!

I didn't respond to the message. I was too lost in my own arousal. But I was stunned when I saw the next text…

iMessage from Ashlyn St. Pierre: u want to see?

I waited for what felt like an eternity to respond. Or maybe it was only a few seconds, who knows. But somehow I knew that this was a point of no return. Up until that point I had just been jacking off to pictures of my sexy ex-girlfriend. That was weird but, well, I’m sure lots of guys think about their exs. But this was different… Did I really want to see pictures of my ex-girlfriend being intimate with her husband? "He's amazing...it's amazing" Her words from five years ago echoed through my brain again. And I realized in a sudden rush of jealous arousal that the answer was... yes. Yes! I wanted to see Ashlyn with the man who had stolen her, conquered her, and fucking married. So, barely breathing, I texted back...

iMessage sent by you: Yes

iMessage from Ashlyn St. Pierre: yes what?

iMessage sent by you: Yes, I want to see your husband getting head!

iMessage from Ashlyn St. Pierre: tell Sebastian. u know how

And so, despite the fact that I knew how wrong, humiliating, and emasculating this was, messaged my ex-girlfriend's husband once again.

iMessage sent by you: Can I please see Ashlyn's little mouth on your dick?

Ashlyn texted me back, though.

iMessage from Ashlyn St. Pierre: this time it's one hundred fifty. And u need to call him sir, thomas

I didn't even hesitate. I opened the venmo app, set up the transfer, and did as she instructed

iMessage sent by you: Can I please see your sexy little wife's mouth on your big dick, sir?

"Oh fucckkkkkk" I moaned out, as my eyes made contact with the next picture. Ashlyn was on her knees, with her big tan naked breasts dangling below her, and with her peachy ass sticking up in the air. She was still wearing the red panties and sheer stockings, and the red straps of her lingerie trailed around her side, hugging her curves. Her long silky black hair was dangling over her right shoulder so that her face was clearly visible to the camera. Her tongue was out and her big blue eyes were staring up at her husband, but I was immediately drawn to the massive dick in my ex-girlfriend's mouth! That was a cock! It was enormous; probably twice as big as mine, and incredibly thick. I could see Ashlyn's tongue sticking out, cushioning his massive member. And then my eyes drifted to over Sebastian.

Fuck… he was honestly even better looking than he had been in his old Facebook photos. The soft light of the room made his impressive six-pack abs almost glow. He clearly knew how to take good care of himself! His body wasn't massive—he certainly wasn't a bodybuilder—but he had an incredibly well maintained physique. His muscular left arm was raised, resting on the back of Ashlyn’s head, holding her hair behind her ear. And I was surprised to see that he was completely hairless. Even his pubic hair had been shaved smooth. I would have thought that this would have made him look feminine, but honestly seeing him smooth made his strong chest and his abdominal v even more impressive. It didn’t help that he had perfect, softly tanned skin. If I'm being completely honest, I would have to admit that he was extremely... sexy. There, I said it. We were practically the same age and yet he looked like a complete stud and I looked ... well, NOTHING like him! I was envious of every inch of his body, and I found myself gazing at his impressive body far longer than I should have. I wasn't gay. I'm not gay. I had never found myself attracted to another man. And yet, I had to admit, seeing Sebastian and Ashlyn together, I was attracted to both of them. Fuck.

His mouth was shaped into an 'O' and his eyes were closed in ecstasy. I had been stroking my dick faster and faster, starting at the perfect duo, when I realized, quite suddenly, that he was cumming right at that moment. I looked closer and I could actually see a spurt of semen flying into Ashlyn’s mouth! He was cumming into my girlfriend’s—sorry, ex-girlfriend’s— his wife's delicate little mouth. "Fuckkk fuckk fuckkkk" As soon as I noticed that I felt my balls tighten up and I let loose. Long ropes of semen oozed out everywhere. Ashlyn had never ONCE let me cum in her mouth, let alone in her tight little pussy. She always insisted that I use a condom. I used to beg and plead with her all the time to let me take the condom off, but she was very insistent that using a condom made cleaning up easy. I couldn't believe he was unloading his spunk into her mouth! "Oh my god" I moaned out, unable to help myself. What the fuck? Had I really just cum looking at a picture of my ex-girlfriend giving head to her husband? Worse still, had seeing HIM naked turned me on almost as much as seeing her?

iMessage from Ashlyn St. Pierre: enjoy that, thomas?

I hadn't acknowledged the photo yet... honestly I didn't know what to say. My hand was still covered with thick, oozy semen and my mind was absolutely spinning. I had literally just spent a hundred and fifty dollars to look at a picture of my ex-girlfriend with her husband's cock in her mouth. What the fuck was I doing?

iMessage from Ashlyn St. Pierre: ummm did u just cum?

Fuck. I had taken way too long to text them back.

iMessage sent by you: Uhh... yes

I typed out my response, feeling embarrassed and yet incredibly turned on.

iMessage from Ashlyn St. Pierre: haha that didn't take long

I could fucking die. How fucking humiliating.

iMessage from Ashlyn St. Pierre: that's really a shame because Sebastian and I have another offer for you... we filmed it last night especially for u...

Holy fucking shit! I felt my heart flutter and, even though I had literally just cum all over myself, I realized that my dick was starting to get hard again. What she serious? They had filmed something together… with me in mind? Was she really teasing me with... well… she couldn’t be serious, could she? "He's amazing...it's amazing..." I couldn't get her parting words to me out of my head.

I still hadn’t responded.

iMessage from Ashlyn St. Pierre: maybe another time

I saw the text and rushed to respond, without even thinking

iMessage sent by you: No wait!

iMessage from Ashlyn St. Pierre: are u sure? It's kinda... intense ;)

iMessage sent by you: what is the video of?

iMessage from Ashlyn St. Pierre: i'm sure you have a pretty good idea already lol

Fuck. My dick was literally rock hard again. My gorgeous ex-girlfriend was offering to sell me a fucking sex tape. I knew it was wrong and yet I knew that I couldn't turn down the opportunity to see it. And, truth be told, I'm not sure what turned me on more: seeing Ashlyn being fucked or seeing Sebastian fucking her. In that moment I knew what I wanted... I desperately wanted to see her athletic, muscular husband pounding into Ashlyn's perfect curvy body. I wanted to see Sebastian fuck his sexy little wife, the love of my life. I wanted to know, once and for all, if he really was as amazing in bed as she had led me to believe. I was so fucking jealous I could scream.

I typed back, already rubbing my aching cock.

iMessage sent by you: Yes, I want it

iMessage from Ashlyn St. Pierre: Oh and it's two hundred

Two hundred fucking dollars? Crap! I was just now realizing them that I had already paid them three hundred dollars. Holy shit. I knew that I really shouldn't be just throwing money away like this. Another two hundred bucks? Fuck, I knew I couldn't turn down the opportunity. I gulped and set up the transfer. The app chimed letting me know that he had received the money.

I walked over to my bedroom, laid down on the bed, and took out the bottle of baby oil that I keep in my bedside table. I unscrewed the cap and allowed some of the oil to slide down the shaft of my five-inch member. I sighed in pleasure as I felt the slippery liquid make contact my cock. If I was going to watch this happen I wanted to do it properly. I lay there waiting for what felt like an eternity; my eyes were glued to the screen as I watched and waited for the file to appear. I even checked the app again to make sure the money had gone through. My balls were rockhard and I realized that I was breathing really shallowly. Fuck, the anticipation was killing me. I couldn't believe that this was about it happen... I couldn't believe that I was going to get to watch my stunning ex-girlfriend get fucked.

However, instead of receiving the video I received another text

iMessage from Ashlyn St. Pierre: we have one little request before we send the video

No fucking way! Anger shot through me as I desperately considered what this might mean. Had she just scammed me out of two hundred dollars?

I typed back furiously.

iMessage sent by you: What?

iMessage from Ashlyn St. Pierre: Well we want to listen as you watch the video... like over the phone

And, having barely registered the meaning of her text, I saw that I was receiving an incoming call. Fuck fuck fuck! What was I going to do? I wasn't sure I could face the humiliation of answering the phone, let alone letting them listen as I watched their sex tape. Fuck me! I had already sent them the two hundred dollars and my phone was dangerously close to sending the call to voicemail. Ughhhh! This was literally the most embarrassing moment of my life and I couldn't believe how god damn turned on I was.

Hesitantly, I pressed ‘Accept Call’ and brought my phone to my ear. "Uhhh hello?" My voice was fucking shaking. Great, just great. I hadn't talked to my ex in over five years and I sounded pathetic.

"Hey Thomas!" Her voice was exactly as I remember it; sweet, clear, and just a tad high pitched. But there was something new there too... she sounded... I don't know... is it possible for her to have sounded more sensual? She sounded amazing and my heart fluttered with longing and desire. I still fucking loved her. God, I hadn't realized how much I still loved her until I heard her voice.

'Are you ready for our little movie?" She asked, after a few second of awkward silence.

"Uhh... yeah, I guess..." I responded, feeling my cheeks growing hot with embarrassment.

"Well then, I think you need to speak with my husband"

Fuck no!

"Sebastian!" She called out, as if he was in another room. "Hold on, he's right here..." Oh. My God. She was going to make me talk to HIM? Not just talk to him... ask him for permission to watch them in bed? This couldn't be fucking happening. My mind was screaming at me to just hang up the fucking phone. I looked down at the big red ‘End Call’ Button and considered it for a second. I could still bail out! But that's when I heard him…

"Sup Bro?" Fuck me! He sounded exactly like the cocky frat boy that I had always imagined him to be. His voice was manly—about as deep as mine—but it was slow and dripping in confidence. In that instant I knew that I hated him... fucking loathed him. I had never felt such a complete and total hatred towards another person in my life. I DESPISED the man that had stolen my girlfriend. The woman who should be MY wife. I couldn't say anything. The words—any words—caught in my throat. What could I fucking say to him?

"Are you still there Thomas?" Ashlyn asked. In that moment she sounded almost exactly like she did when we were dating.

"Ummm yeah... I'm here... uhh... sorry"

"Ok, I'll just text you what you need to say"

And that's when her text message lit up my phone. I felt dizzy and disoriented as I read what they wanted me to say. I was already completely humiliated but this was one step too far...

"Ashlyn .... come on...” I spluttered “I can't say that...Please!"

I heard two beeps and saw that the called had been ended! What the fuck! She had just hung up on me. I groaned in anger and actually slammed my phone down on the coffee table. No fucking way. There's no fucking way that I wasn't going to get the video I paid for... I waited and waited and waited, yet nothing happened. "Fuck it" I said to myself, picked up the phone, and called her number. She answered almost immediately.

"Change your mind?"

"Ummm... well..." I said, feeling my breaths come in quick bursts.

"...well?"

I sighed, and gave in. I gulped silently and said the most humiliating sentence that I had ever uttered in my life:

"Uhh ... Can I ..." I steadied myself and tried to put the words together "Can I please see how you fuck your insanely sexy wife, Mr. Scott?"

I repeated the words exactly as she had instructed, which was difficult because I could barely breath. I felt like my heart was going to beat out of my chest. I had NEVER felt so fucking humiliated in my life. And I had NEVER felt so incredibly aroused. My erection was so hard that it was on the point of being painful. Then, my humiliation multiplied.

"Haha" He laughed. He was fucking LAUGHING! A short, cocky, frat boy laugh, as if he was amused by something a little kid had said. Fuck me. I could have fucking died of embarrassment at that moment. "Sure Bro, no problem"

"Ok Thomas, I'm sending you the file now" Ashlyn said, evidently taking the phone from her husband. "I'm going to put us on mute, but you need to keep your microphone on. Turn up the volume on your phone so that we'll hear the video as you watch it"

I didn't say anything, but I silently turned up the volume as she had instructed.

"All set, Thomas?" She asked.

"Yes" I said... it was almost a whimper. My cock was throbbing with anticipation.

Then, finally, I saw that Ashlyn was sending me a file. I sat there, holding my breath, as the video slowly downloaded itself onto my phone. I couldn't fucking believe that this was happening. 40%.... 60%.... 70%... 80%.... 85%.... I felt my heart thumping widely in my chest. I needed this. I needed to see it. I needed to experience it. After five years I was finally going to see my beautiful girlfriend fuck the man she had left me for.

"Oh, and Thomas?" She said, as the file hit 90%. I gasped, unable to say anything.

"I had a REALLLLY good time making this video for you"

As she finished the sentence, I heard the static on her end go silent and the file finally finished downloading; they had put themselves on mute. As the video automatically expanded into life I involuntarily moaned out "Ohhh fuckkk!" So much was happening that I was completely overwhelmed. The camera was pointed at their bed, which was covered in silky grey sheets. The video was clearly filmed at night, because there was a soft blue light emanating throughout the room. The sounds and sights of passionate love making hit me immediately. The first thing that I saw was Ashlyn. And fuckkk… she looked amazing. She was on all fours looking towards the camera, but at a slight angle so that I could see her entire body. She was clutching the silky sheets of their king-sized bed in her small fists for support, as she rocked back and forth. Her long shiny hair was pulled back over her right shoulder so that I could see her body moving without any disruptions. She was holding herself up on her elbows, yet her back was arched and her peachy ass was high up in the air. She was rocking backwards and forwards, making her enormous tan tits sway beneath her. I could hear the bed squeak as her big tits danced towards the camera. Her eyes were closed (fuckkkk that makeup made her eyes look amazing) but her glossy lips were hanging open, making a wide 'o'.

“Oh Ashlyn” I moaned out, involuntarily. I immediately began working my hand up and down my rock hard shaft, and I heard the familiar squishing sound as my fist made contact with the baby oil. My hand, coupled with the baby oil, was making an audible "thump, thump, thump" as I beat off looking at my gorgeous ex's body. It registered in my brain that they could probably hear me masturbating, and my intense humiliation caused me to slow down in an attempt to silence the sound of my emasculation. She wasn't completely naked and I could see that she was wearing the same red sheer one-piece lingerie set and stockings from her earlier pictures. The sheer red bra was dangling off her waist, allowing her tits to dance below her, but she was still wrapped in the delicate red straps. And she still had the tiny red panties on. But they were pulled over to the side by her creamy white thigh. And that's .. well... that's when I saw him. Sebastian FUCKING Scott.

I heard myself gasp out "Holy Shit” and my hand resumed furiously jacking off. I knew they could hear me... knew that they were listening in on the most erotic and humiliating moment of my life... but from then on I didn't care. Their phone remained on silent and as I continued to watch it became easy to forget that they were there.

Sebastian was fucking my perfect ex-girlfriend like a Greek God! He was on his knees behind her, thrusting into her tight pussy in time with her movements. His big hands were wrapped around her voluptuous curves, and he was using her thick ass as leverage to pound into her. Fuck, he looked good! I had never fucked her like that before! They had obviously been screwing for a few minutes before the video started, because his six pack was shiny with sweat and I could see the veins popping out of his forearms as he fucked the love of my life. He really was an Adonis.

My attention shifted back to Ashlyn, as she tossed her hair to the other side and arched her neck back to look up at the handsome face of her husband. "Oh yessss babbyy! Just like that. You're fucking me so goooddd Sebastian!" She started grabbing more and more of the delicate silky sheets to use them as leverage as she began grinding her body back to meet Sebastian's thrusts. I heard myself moan her name not once, not twice, but three times as I stared at her. "Oh Ashlyn... Ashlyn... Ashlyn!" She looked incredible and I noticed that she had started rolling her body back in rhythm with him. It was amazing.

Sebastian grunted as she started grinding into him harder and harder. "Yeah that's it babby. You gotta move that fucking pussy on Daddy's cock. That's it baby" I couldn't believe how insanely sexy she looked, giving her husband complete access to her voluptuous body. She literally looked like a porn star. And I didn't know how much longer I could hold back my cum. I reached for the bottle of baby oil and poured more oil down my dick, splattering my hardwood floor.

They were both moaning and staring passionately into each other's eyes as they fucked. He was fucking her at a brisk pace, making the bed squeak with each thrust. I heard Ashlyn sensuously moaning out "Ohh ohh ohh", and heard myself join with Sebastian as he groaned out "Ahhh ahh yes!" His voice was deep, musky, and incredibly masculine. I could hear his balls slapping against her peachy ass, and I felt myself slow down just a bit to perfectly time my motions with his. I moaned as I saw pre-cum starting to bubble up through my raging dick.

"How's Daddy's cock baby?" He asked her, sliding his hands along her soft, tanned back. He slid his hand up to her left shoulder and pushed her face down towards the bed, granting him even deeper access to her tight young pussy…. His wife's fucking pussy. Her tits disappeared into the silky sheets but her back arched higher than ever before, making her ass look as delicious as ripe fruit!

"Soooo fuckinggg goooddd" She purred, turning her cheek so that she was looking towards the camera. "Ohhhhh Sebastian! Ohhh babbyyy!"

"Holy fuck" I moaned loudly. I was far past caring that they were listening to me watch their sex tape.

"Mmmmm" Sebastian grunted. It was a deep, masculine, almost animalistic sound. "Mmmmm yeah baby... take your husband's fucking cock"

As he said it he looked up from Ashlyn and stared directly into the camera. "Oh my god" I gasped, as his eye narrowed and he began to speed up his movements, still staring directly at the camera. It was like we were staring directly at each other! His chiseled pecks shined and glistening abs began to flex as he started to pick up speed. And I could hear his rock-hard balls slapping Ashlyn's wet pussy again and again and again! Fuck, she was so fucking wet! Almost subconsciously I began beating myself off faster and faster to match his speed.

He reached down and grabbed Ashlyn's hair, gently pulling her up on her elbows as high as she could go. "Oh Fuck... Ashlyn!" I moaned out, as her heavy breasts came fully into view. Her big tan tits were facing directly at the camera, and I could see that her nipples were as hard as diamonds. As if he was sensing my thoughts, Sebastian reached forward and grabbed one of her bouncing tits. Ashlyn squealed out his name as his big hands began kneading and massaging her breast. "Oh Sebastian!" She purred.
"Fuck... look at those tits!" I gasped out, rapidly beating my raging hardon with one hand and putting the other over my gaping mouth. I knew that I couldn't last much longer...

"Mmmmm.... mmmmm baby!" Sebastian roared, now thrusting into Ashlyn with considerable speed and vigor. I could hear each thrust echoing through the bedroom. I could hear how wet her little pussy was.
Ashlyn was purring and moaning, and I noticed that she was now looking alternately at her husband and at the camera with each thrust. She looked over her shoulder at him, and then darted her eyes to the camera, and then glanced back at him. For some reason seeing her look back and forth like that... almost like she was looking from him to me and back to him, almost brought me to climax. "Yeahh fuck that pussyy" She squealed. "Fuckk that pussy Daddy"

"Tell me what you told me last night, baby!" Sebastian roared, putting her mouth right next to her ear. He began sucking on her earlobe and, as his mouth made contact with her skin, I saw Ashlyn's eyes flutter in ecstasy. I always loved when Ashlyn had licked my earlobe during sex! "Oh my goddddd!" I moaned out.

"Uhhhhhh" Ashlyn moaned "Last night I told you that you were the BEST fucking lover I've ever had!"

"Fuck yea baby” He moaned. “But how many men have you fucked?" Sebastian asked, in a cocky, teasing, arrogant way. Fuck, he was a confident shit!

"Ohhh fuckkkk" Ashlyn moaned, putting her hand over Sebastian's and gliding it around her soft delicate nipple. "You know I've only ever fucked two guys, baby. You and ughhhhhh THOMAS. FUCKKKK"

She actually screamed the last word because Sebastian suddenly began fucking her with a burst of incredible speed. It only lasted for a few seconds, but it was extremely impressive. Thump! Thump! Thump! Thump! Thump! He roared and he slowed down again, bringing his mouth to her cheek.

I had actually gasped out "FUCK" at the same time as Ashlyn had, but for a very different reason. At long last my suspicions had been confirmed: I had been Ashlyn's only over lover.

"Ohhh yeah." Sebastian moaned, kneading her breasts. "Did he ever fuck you like this baby?"

My head was swimming and my cock was almost at its breaking point. They were talking about ME? As they were FUCKING? "Oh my god!" I gasped. I couldn't believe that he was actually asking her to compare our prowess in the bedroom. I looked into Ashlyn's face... the love of my life... and we both gasped out the same answer

"No!" I whispered. She had, however, screamed it out, and the word seemed to echo through their apartment. "NOOO!” she screamed. “No fucking way, Daddy. NEVER" She moaned. "We only.... ahhhh.... ever fucked in one position. I was ALWAYS on top!"

Sebastian snickered... he fucking snickered in her ear as he continued to thrust into her. He continued to run his hands around and around her heaving breasts. "And did that ever make you cumm baby?" He asked, at almost a whisper.

I held my breath as she squeaked out the answer "Uggggg NO!"

"Then when did you have your first real orgasm Ashlyn?" Sebastian asked, at almost a whisper.

"Uhhhhh Sebastian... the first time WE fucked!" She squealed the answer as he squeezed her tit. “Uhhhhhhh” I moaned out. I was past the point of being able to put my thoughts and emotions into words. I had shifted into pure animalistic lust. I knew that I should be mortified that they were talking about me—making fun of my poor performance in the bedroom— but it made me even more enthralled in their lovemaking. The only sound in my house was the rhythmic, squishy thumping of my hand up and down my rock-hard shift. I drenched it in even more baby oil and knew that my orgasm would come any minute.

"Yeah, But WHEN baby?" He asked, as if they had had this exact conversation dozens of times before. “When did you first cum?”

"Uggggg" She moaned out, sensuously. "It was … it was… in the first TWO minutes! I had NEVER felt anything like your massive cock, baby!" As she said the words—the confirmation of my total inadequacy as a man—I felt my legs spasm and shake as I beat off harder and harder.

"And what did you say to me right after?" Sebastian asked, in a low soft voice. He suddenly stopped thrusting and brought himself to rest balls deep inside Ashlyn's tight young pussy. The rhythmic thumping of his hard body against her soft ass was replaced by their heavy breathing. He removed his hand from her tit, licked his finger, and began slowly circling her clit. His finger was less than an inch from his thick cock.

"Uhhhh.... Ahhhh" Ashlyn's breathed slowly, in and out, as she began to rotate her hips, grinding his massive cock. Her breathing was getting more and more labored with each passing second. "Uhhh ... I said... I said... " She gasped. "Sebastian FUCKKK" She squealed, as he began to rub her clit faster and faster. "Please don't stop, daddy! You're gonna make your wife cum. Please don't stop"

"Ashyn!” Sebastian moaned, breathing quickly himself. “What did you say to me right after you came the first time?"

"Ahhhh I said… I said…. I NEVER wanted to fuck my boyfriend again!" Ashlyn moaned, bringing her delicate hand up to wrap around the back of his neck. She brought his lips right up against hers, and they stared directly right into each other's eye.

"OHHHHHH" I moaned, feeling my dick about to blow

"And what did you do six months later?" Sebastian whispered

"I fucking MARRIED YOU!" Ashlyn squealed. "OHHHHHH SEBASTIAN!"

Two things happened at once. Ashlyn screamed louder than ever before and her eyes fluttered in ecstasy. Her scream seemed to echo through their entire house. Her beautiful tan body shuddered and she suddenly pulled his mouth forward, giving him the most sensuous kiss that I had ever seen in my life. He responded by squeezing her tight; his dick was still deep within her pussy, and I could hear him moaning as she covered his mouth with hers! They were slobbering all over each other and she was shaking violently. Then it hit me: she was fucking cumming.

I mentioned that two things happened at once. What was the other thing? I exploded EVERYWHERE. Literally, my cock exploded. I roared as my balls tightened and sent wave after wave of thick, sticky semen up through my dick. Cum leaked out over my sheets and over my blanket. It went everywhere. I swear that globs of my cum even splattered my bedroom window and my mirror. It was the kind of orgasm that is so intense that it's almost painful. Hearing her say that she had married him six months later had finally sent me over the edge. My girlfriend, Ashlyn St.. Piere, had become his wife—had become Mrs. Ashlyn Scott— less than a year after we had broken up. His conquest of her had taken only six months. And yet, she was his completely. And I couldn’t blame her.

Even though I had just cum myself silly, the video hadn't ended. There was another thirty seconds or so of film left. Ashlyn was slowly catching her breath. They ended their kiss, and she was heaving in and out… her breaths came slower every second, and she looked as though she had just experienced total pleasure. "…And what did you never let him do to you, baby?" He purred in her ear.

"That's easy..." She whispered, wiping a delicate bead of sweat from his brow. "I never let him cum in me"

And at that moment, Ashlyn's husband pulled his still completely erect dick from her pussy and allowed her to lean back into his arms. They sunk back towards their headboard and Ashlyn flipped over to straddle him, locking her lips on Sebastian's mouth in another sensuous kiss. Her back was arched up, and her big peachy ass was facing directly towards the camera, as she lay passionately kissing her husband. She was still wearing the red panties, but they had been so badly stretched that from his angle I could clearly see her glistening pussy. And that’s when I saw it.... his hot, sticky, gooey cumm was leaking out of my ex-girlfriend's tight young pussy onto the silk bedsheets. "Oh Ashlynnnnn" I moaned. I dropped my phone and looking down at the cum coating my hand and stomach. I couldn't fucking believe I had just had the BEST fucking wank of my life to a sex tape of my ex-girlfriend and her stud of a husband. What the fuck was wrong with me?

I knew in my heart—at that exact moment—that was he, indeed, the better man.

--

I was dizzy and disorientated. I was completely exhausted and literally felt punch drunk. I had lost all track of time and all perspective. I looked at the clock on my bedside table and realized—fuck!—it was almost two o’clock in the morning. I knew that I needed to clean myself up, but I couldn't quite bring myself to move. And that's when I heard the sound of static on the phone again. HOLY SHIT. I had completely forgotten that Ashlyn and her husband were listening in on me. I froze. I barely breathed. I couldn't move. That's when I heard her voice

"... mmmm that was fun. Sebastian and I had a great time. Well, goodnight!"

I didn't move a muscle. I just laid there, starting at my phone on the floor.

"Oh, and Thomas?"

"...yes?" I whispered.

"Next time, you can just give us cash..."

I was speechless.

"…I think you'll be seeing a lot more of me and my husband from now on"