Hello,
My ex girlfriend's name is Isabella and I dated her for the last couple of years of university. We were in our early 20s and she was very pretty and fairly quiet and shy personality-wise. Her massive boobs helped a lot too, not to kid anyone.
She came across as very sweet and innocent but once we'd been together for a while she started to tease me with insights into her sexual past. She showed me a dick pic that her very first boyfriend sent to her and teased me about how this was the first penis that had ever been inside her. She even shared details of what she had done with other men before me like where they had sex, what positions they had used and how this made her feel.
I was surprised when she told me that she had already had sex with six men, especially because she came across as so innocent. It was obvious that she enjoyed having sex whenever she had the opportunity but she was always very discreet about it and did not think of herself as a slut.
When we started having sex she was very clear that she preferred sex without a condom and that she wanted me to cum inside her because she felt that this was the most important part of sex, and she told me that she had always done this with the other men she had been with as well.
It got very turned on by her giving me these insights into her most private and intimate moments. I thought a lot about her having passionate sex with the men before me and how satisfying this was for her and how much she cherished those experiences, and I found this very arousing. I think it particularly turned me on to sexualize her like this in my mind because of how sweet and innocent she seemed to me.
Although our relationship had become quite serious at one point and we had even started talking seriously about marriage and family, about two years into our relationship as we were approaching graduation we started to grow apart. We continued with our relationship for another year but it was clear in hindsight that things were going to end even though we hadn't officially broken up.
She did some of the things that people often do after a break up like changing her hair style and buying lots of new and different clothes. We still spent a few evenings together each week though and I tried to initiate sex as often as before, although while she rarely turned me down before, she started to deny me almost every time now and made unconvincing excuses about not feeling well or having a lot of work to do. I started to suspect that she was getting sex from somewhere else or at least was trying to.
We lived separately with our own friends so I didn't have any idea what she was doing most of the time. I had been able to guess her social media and email passwords so, after maybe three months of our relationship floundering and me growing more suspicious of her, I started logging in to her accounts to check up on her. I didn't find anything for some time and started to think I was just being paranoid but then one day an email confirming a reservation for a hotel in our city appeared in her inbox and I could see the she had forwarded it to another email address with a winky face emoji. The reservation was in a few days and I noticed that it was for a night that she had told me she was going out with a group of her friends from her course who I didn't know. I couldn't think of any reason why she would need to book a hotel in our city or why she would need to forward it to someone else with a message like that.
My heart was racing with the implication of what I had just seen. I had a strong feeling that I had just seen something that I shouldn't have and I didn't know what to do so I quickly logged out, closed my computer and went to do something to take my mind off it. At first I wanted to confront her or talk to someone about it but all of that would have involved admitting that I had been spying on her emails and I wasn't willing to do that. After some reflecting, I decided that I wanted to investigate further so I did something extremely reckless that I still can't quite believe I did. I logged back on to my computer and made a reservation at the same hotel for the same night.
On the day of the reservation I went to the hotel in the late afternoon to check in. I mentioned that a friend of mine also had a reservation for the same night, gave them my girlfriend's name and asked for the room next door. They told me it was no problem and said that "her boyfriend" had already checked them in earlier but had left, and the room next door was still available. But I was her boyfriend! It could have just been a mistake but the painful thought immediately flashed into my head that the person my Isabella had sent the email confirmation to must have been a guy and that he had already check them into the room with the hotel staff assuming he was her boyfriend. It was hard for me to maintain my composure with all of that going through my mind. I felt my face turning red and I fumbled my room key as they handed it to me before I turned to head up to the room.
It was a fairly cheap hotel and when I got to the room I was pleased to find that the sound proofing wasn't great between rooms so I would be able to hear into the next room quite well with my ear to the wall. I also looked at the fire exit map on the door and noticed that the head of the bed and the bathroom in their room were against the wall adjoining my room, which I thought would help me to hear what was going on in there.
I headed back to my flat afterwards. I started to have serious second thoughts about what I was planning to do as the evening approached. I almost went to her house to confront her about what she was going to do and a few times I thought I had decided to just forget about the whole thing and stay at home with my friends but I had come this far and I had to be sure otherwise it would play on my mind endlessly so I eventually resolved to go through with it. At around 7pm I received a text from Isabella telling me that she was heading out to see her friends. Her route into town went past my flat so I sat by the window waiting for her to pass and as soon as I saw her, I headed out to follow her, wearing a cap and coat that belonged to one of my flat mates so she wouldn't recognize me as easily.
As I followed her from a distance I noticed that she was wearing a tight blouse, tight mid-thigh skirt with opaque black pantyhose and knee-high leather boots - one of her new outfits that she had referred to as her "sexy one". I was still desperately hoping that I had misunderstood everything and that she really was just going to meet her friends but with the emails, the hotel and now her wearing this outfit, it seemed more and more inevitable that she was going out to meet a lover.
I continued to follow her into a quiet part of town and saw her go into a bar that I had never been to before. The bar had a huge front window right on the street and after a few minutes I walked past it, glancing through the window from under my cap to try and spot her. It took a few passes but eventually I noticed her sitting at a table with a guy. I didn't dare stop or look at them with any more than a short glance but it was clear from their body language that this was not just a friend. After a couple more passes I recognized the guy. He was one of the young university lecturers from her course. I had briefly met him a few times when he was chatting to Isabella when I picked her up after her lectures and apparently their chatting had escalated into something more. I had sensed some chemistry between them but when I mentioned it to my her she laughed it off and told me he was over ten years older than her, married and has at least one kid. Perhaps I should have been more suspicious but if he really was married then it made more sense that they were only able to meet at a secluded bar and had to book a hotel to have a private place to have sex.
I walked around outside for around half an hour and then went to my hotel room. I sat there quietly for over an hour, not knowing what I was doing, and then suddenly, at around 9:30pm, I heard the door to their hotel room open and close, and then muffled voices through the wall.
I quicky jumped up from the bed and sat on the chair that I had positioned next to the adjoining wall and listened carefully. It was definitely her voice and a man's voice and I could tell from the way she was talking that she was at least a little drunk. Their talking was quite muffled through the wall but I caught a few sentences like "I can't believe we're finally doing this" and "let's get you out of those clothes" that seemed to confirm what they were going to do, as if there was any doubt by now.
I sat quietly and continued to listen to what sounded like them undressing and then a heavy creak that sounded like them getting onto the bed. I heard more muffled talking and giggling and then after a few minutes I started to hear her heavy breathing and the familiar and unmistakable sound of her quietly moaning with pleasure as it sounded like he was fingering or going down on her. This went on for a short while and the whole time a voice in my head kept telling me to run out and start banging on their hotel room door to stop them. "It's not too late!" the voice said, "there's still time to stop her!"
Suddenly, after some more loud creaking of the bed, I realized that it had gone quiet. I thought to myself "maybe they have stopped - maybe she has she change her mind". Then after around a minute of silence I heard the bed begin to rhythmically squeak, quietly at first and then louder and louder, with the unmistakable sound of two people making love. I realized with a huge gut punch that when it had gone quite, it wasn't because they had stopped, it was when he was pushing his erection into her body.
I couldn't believe it! My suspicions about her were right and I had caught her cheating on me red handed. It was happening right there and I would have been close enough to reach out and touch them if the wall hadn't been between us. I could hear everything through the wall. As they continued to make love I heard their heavy breathing and the desperate "uh" and "mmph" sounds she made each time he thrust into her. I heard him say things like "do you like my big cock inside you?" and "do you like how I'm fucking you?" and every time I felt my stomach drop as I heard her sweet and familiar voice reply.
Yet to my surprise I felt myself getting hard. Almost without thinking, I took my cock out and started to masturbate. I hadn't realized until now just how much her teasing about her sexual past had turned me on and how arousing I found the idea of her making love to another man. I started to picture them only a few feet away, his throbbing cock deep inside her, vigorously thrusting into her, their hot and sweaty naked bodies writhing together, their deep and passionate kissing, and how aroused she must be at this very moment thinking she was doing this in secret.
After almost ten minutes I heard them change position. I couldn't hear them as well but could still hear the bed squeaking to the rhythm of their sex. I continued to masturbate to the sound of their love making, almost cuming a few times but holding on to prolong the thrill of what I was doing. After another ten or fifteen minutes I heard the rhythm start to increase her say "yes, yes, yes" with a loud and excited voice. Then I heard a sudden loud and satisfied gasp from both of them as it sounded like he started to cum. I couldn't hold on anymore and I exploded in one of the most intense orgasms I have ever had right at the moment that another man was cuming inside my girlfriend only a few feet away.
I slowly came back to reality and looked at the semen spattered carpet in front of me and listened to the sound of Isabella and her lover finishing their sex. This was surreal. I felt confused and slightly disgusted with myself for what I had just done, but also disgusted with Isabella for how she had betrayed me.
For a few minutes I heard very little from next door as presumably they both lay on the bed exhausted. This gave me some time to think and an idea popped into my head to text her now to see how she reacted. I took my phone out of my pocked and, not being able to think of anything more interesting, I sent her a message along the lines of, "hey, I hope you're having a good night with your friends. I was just wondering whether you would like to get together tomorrow".
I heard her phone buzz through the wall immediately and I heard the sound of the bed creaking followed by fumbling and then a few moments of silence. I was not expecting her to get up straight away only a few minutes after finishing having sex with her lover.
"Everything alright?" I heard him say.
"Umm, yeah fine" she replied, "just some guy".
"Oh, you mean your ex? Is he still texting you?"
"Yeah" she said with a sigh.
"Good thing he doesn't know what you're doing tonight!" he said with a laugh, followed by a loud smack that I assumed was him slapping her bare ass.
So she had lied to him too and told him that we had broken up....
A few seconds later I received a text saying "good thanks, not sure about tomorrow, I'll have to let you know". I couldn't believe she had replied to me, her boyfriend, having literally just finished having sex with another man and was still lying naked next to him.
A few more minutes passed and and I continued to listen to them talk and giggle with each other. At one point it sounded like he had started to playfully tickle her and I heard her quickly say, "No, no, don't! I can feel your cum leaking out!"
So she had let him cum inside her! I had hoped that the brief silence before they started having sex was him putting on a condom because I hated the idea of her sharing something so intimate with another man. However, I knew that if she was going to have sex with someone, she would want to take their cum inside her, and somehow the thought of his bare cock deep inside her body and filling her with cum turned me on even more.
"I need to go to the bathroom" Isabella said and I heard the loud creaking sound of her getting off the bed and her footsteps as she went into the bathroom and closed the door.
I quickly moved down the the adjoining wall to the part opposite the bathroom and continued to listen. I knew exactly what I was listening to as she always did the same things after we had sex. I heard loud dripping sounds echo in the small bathroom as she squatted over the toilet and let his semen drip out of her. Based on the number of drips it sounded like she had taken a huge load from him and I even heard her quietly say "oh my god" to herself a few times as it kept coming out. I then heard her put the toilet seat down to sit on the toilet to urinate, and finally rip off a handful of toilet paper to wipe the remaining cum and wetness from her pussy and the inside of her thighs.
I heard her return to the bed and very shortly after heard him start to moan with pleasure. It wasn't clear what they were doing until I head him say "on yeah, suck that cock - take it nice and deep". I listened harder and heard what I assumed were sloppy sounds of Isabella taking another man's penis into her mouth. I couldn't believe how eager she had been, starting to suck his cock almost as soon as she had returned from the bathroom. I was imagining Isabella's sweet mouth and lips that I had so often kissed now wrapped around another man's hard cock and her mind totally focused on giving him pleasure. After a few minutes, I heard a sudden gasp followed by heavy breathing.
"You're so big" she said, between deep breathes, "I can hardly fit you into my mouth let alone down my throat".
This hit me hard like a slap in the face. I felt that I was a good size but she could usually take me deep in her mouth without any difficulty so this seemed like confirmation that the cock she was taking was considerably bigger than mine.
"Mmm, I love the taste of myself on you" she said, right before I heard more sounds of her sucking his cock.
I just sat there quietly and listened to Isabella use her mouth to pleasured another man and then after a few more minutes I heard the now familiar sound of them repositioning themselves on the bed followed by the rhythmic sound of their love making. I felt the same arousal as the first time and masturbated to the sounds and imagined images of her naked body being vigorously fucked until I came again along with him.
I listened to them have sex twice more before my cock was too sore to carry on masturbating. It sounded like they were planning on spending the whole night and morning having sex and I preferred not to listen anymore or to risk bumping into her when they checked out in the morning so I left my hotel room in the early hours, dropped my key in the checkout box, and walked back home and went to sleep.
I slept surprisingly well but felt numb and empty the next morning after my experiences the previous night. In the afternoon I texted Isabella and arranged to come over to her place in the evening.
When I arrived we went to her room as usual, sat on her bed and started to catch up. She was almost her usual self but she behaved quite strangely and avoided making eye contact with me, which I felt was because she was ashamed of herself for meeting me so soon after what she had done last night. What concerned me most though was that I remember her behaving in exactly the same strange way at least two other times during our relationship, both after she had been away somewhere, and it made me realize that she probably had sex with someone else without me knowing about it on those occasions as well.
After a little while Isabella left the room to go to the toilet and I took the opportunity to look in her laundry basket. As I expected I saw the blouse that I had seen her in last night, but I also saw a very nice black lace panty and bra set and a pair of opaque black hold up stockings that I had bought for her last year. So it wasn't black tights she was wearing under her skirt last night, she had worn stockings for him! While I could still hear her in the bathroom I went in for a closer look and I could see damp patches at the top of the stockings where it looked like her lover's semen had leaked out of her and ran down the inside of her thighs, which confirmed that she had worn these throughout their love making.
After she came back to her room, we started watching TV. I wanted to confront her but I felt like the moment had passed and I didn't know what to do, although I knew I felt incredibly horny sitting up next to her and thinking about what I had heard her doing last night. Without thinking about it I started stroking her thighs and kissing her, which was one of the ways that I tried to initiate sex with her. I could sense her reluctance at first and was expecting her to turn me down as usual, but after a few minutes she jumped up to turn the light off and started to get undressed.
The way she looked at me and the speed with which she took her clothes off made it clear that she was extremely horny. I gave her oral sex and she came much more quickly than usual, presumably from the knowledge that another man had cum inside her at least four times less than 24 hours before. We then had some vigorous and passionate sex and she was very enthusiastic even though she must have still been sore from the night before. She came again as I came inside her, which I think was from the thought of her having semen from two different men inside her at the same time, which she had previously told me was one of her fantasies.
I surprised myself by initiating sex with her and eagerly going down on her although it seemed that just spying on her the night before wasn't enough to satisfy my voyeuristic kink. I had to have my mouth and cock in the same space that her lover's cock had been so recently. I wanted to taste her pussy and the traces of his cum that would inevitably still be there and I wanted my cock to soak in the remnants of his cum deep inside her and then to fill her with my own cum to feel like I had reclaimed her body.
We continued to see each other and have sex occasionally for around another six months before we finally broke up. She continued to cheat on me and I continued to pretend not to know.
We met up a couple of years later and she gave me a tearful apology for mistreating me when we were together, although she was never specific about what she meant. I took her back home and fucked her as hard as I could bareback and came inside her twice.
I think she wanted to make up for what she had done. But that experience still affects me and my sexuality with girls I date today.
Toby
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