I was a voyeur in my ex-gf's window | 2016

This story is 100% true and I instantly get hard whenever I think of this moment in my life.

I’ll give a little background before I start. Dated this girl, let’s call her Amelia for about 6 months in my senior year of college. She was 21 years old and I was 23 when this story happened.

Amelia was about 5’3, petite, with A-cup boobs and dark red hair and pale-ish skin. I have an average size penis, (6 inches length, 6 inches girth) nothing overly special. Our sex was good and we did a lot of fun things like blindfolds, tying each other up etc.

Anyways by second semester senior year of college I decided I wanted to live my final two months of school, single. Or so I thought.

After on-and-off fights through January and February, I broke it off with her in mid-March, in order to hook up with as many girls as I could before graduation. I broke up with her on a Friday morning and went off to a mutual friends party that night. I figured Amelia; being left heart broken by me earlier that morning wouldn’t come out. I was right; she was nowhere to be found which meant I could let loose without the worry of her hooking up with someone in front of me.

Anyways, back to me for now. I had limited success in wheeling and only managed to make out with some incredibly drunk girl before I wandered my sorry ass home. Not exactly the night I was anticipating.

I woke up hung over and feeling depressed on Saturday and I knew I could instantly feel better if I just called up Amelia. However I was able to get through the day without contacting her.

Most of my friends weren’t up to anything too crazy that night so I decided to stay in with my roommates, have a few beers and watch the Blackhawks game. I don’t know why but I couldn’t shake this guilty feeling about ending things with Amelia.

Flash forward, around 3am I woke up with a high feeling of anxiety and in my anxious moment I called Amelia. She didn’t answer. I texted her and I could tell she had not read them. I figured she had gone to bed but I just had to see her.

She lived a mere 3 minute walk away, so on the unseasonably warm night I decided to stroll to her house and sneak up her fire escape in order not to wake her roommates with the doorbell.

As I approached the back ally behind her house, I was quite surprised to see light still on. I can remember so well this weird rush of anxiety that came over me as I quietly walked up to her third floor window. What if she was in her room with some other guy?!?!

Before we had dated she had had a few random one-night hookups but she never delved into much detail about them. As I ‘oh so quietly’ approached the last few steps I realized her window was open just a small crack (it always got so warm in her room). I crept up to near the side of the window, her cheap shutters were closed but there was maybe 2 inches of space between the windowsill and the bottom of the shutters.

I peered in to see her on her knees blowing this guy Ryan who I knew of, but certainly didn’t know well. She had her pants off and was in a black tube bra.

A huge array of motions came over me. I felt sick to my stomach. My ex-girlfriend of less than 48hrs was blowing a guy and I was witness to it. IT WAS LESS THAN 10 FEET FROM ME!

His dick was massive. I could tell because she was working both hands on it, where with me she really only ever used one.

The jealously was running through every corner of my body, but I suddenly realized I was so incredibly turned on. I couldn’t stop watching as I was knelt down there on her third story fire escape. I can literally remember looking at the redbrick of the building think “is-this-actually-happening-right-now?!?”

In what seemed like an eternity, but probably no more than a minute of me arriving he had put her tight body on the bed and took off her lacey black thong. He proceeded to eat her out as I just knelt there helplessly as my ex moaned. I could not believe this was happening.

I realized that my body was shaking with excitement and I couldn’t believe how hard I was. I had no inclination as to whether or not I would be seen by one of the neighbors; I was so fixated on what was going on.

Ryan eventually got up walked towards her desk and put a condom on. As he thrust inside of her my heart sank. From my vantage point his dick looked so much bigger than mine and her moans made it seem that way. She was kept whispering loudly under her breath “Oh Ryan…Oh Ryan…Oh Ryan”

As he thrust into her in the missionary position my body told me I had had enough. I turned away from the window, walked down two-three steps and sat in disbelief.

What had I done?

I broke up with a perfectly good girl in order to have meaningless hookups and now she is ten feet away from me getting fucked. Why had I been so stupid?

I could hear her moan as I sat there for another few minutes. My heart wanted to walk home and cry myself to sleep but my dick wanted me to peer back in her room. When I looked back in I saw her riding him, her ass facing me. She bounced up in down moaning even louder than before. I was surprised her roommates didn’t hear. I couldn’t remember her being that loud with me.

At that point I decided to wander home and masturbated before falling asleep.

I woke up to an 8am response to my earlier texts, with her telling me she had fallen asleep. We agreed to meet for coffee and talk but at that point I was crushed. We talked over coffee and we agreed we weren’t meant to be. I never told her, or anyone else, about what I saw that night.

It’s a moment in my life that I STILL jerk off to the thought of.

To any guy who is reading this, be careful what you wish for. The universe has a funny way of screwing you over.

The end.