Also posted at [r/cuckoldstories](https://www.reddit.com/r/cuckoldstories/), but I figured it might be enjoyed here too.
This story is mostly true. It is a composite of a three separate of events, but makes for a better story when told together. There are also some embellishments and names are changed, but is honest otherwise. This first post is mostly setup, but it’s non-stop after that. Enjoy!
Steph and I had been dating for just over two years. Steph is a stunning, 22-year-old 5’4″ brunette with a great body. She’s curvy and looks stunning with E cup tits that are great for her body.
We met in college and hit it off straight away, and the two years of our relationship up to now have been good, despite the odd argument. Everything was going fine up until a few months ago. Recently we’d both been stressed with work and grad school, and our sex life had been struggling as we were less focused on each other. Having opposite work schedules where I work nights and she works days, with only one night a week together, made it worse. This, teamed with the excitement that comes with a new relationship wearing off, resulted in us only having sex about once a week instead of once a day like we used to. I think that part of the problem we were having was that Steph wanted me to take charge and take the initiative, which I struggled with.
Whenever I asked about previous boyfriends, she would tease me about how many men she had been with and how few women that I have been with. She also tells me about sex with her two most serious ex-boyfriends. This has led to me asking her questions like “What’s the sluttiest thing you’ve ever done?” and “How many cocks have been in your mouth?” She said the sluttiest thing was a threesome with her best friend in high school to impress a guy. To the second question, Steph answered that she “honestly didn’t know how many” with a small smirk on her face which made me a bit jealous. Steph then joked about how easy it would be for her to suck a random guy’s cock and fuck him one day by telling me she was going out to meet friends. This was the first time that this sort of thing had turned me on but I didn’t think much of it.
She broke up with Chris, her last boyfriend, just before college when he moved away, and there was a 5-month gap between that and when we met. Steph has told me that the sex with Chris was really good. Apparently “he knew what he was doing” and used to dominate her “just how she liked.” They broke up when Steph found out Chris had been fucking a girl (who Steph hated and suspected) for over a month. After this, Steph told me that she hated Chris and she promised herself that she would never talk to him again.
She told me that she took the break-up badly and over the 5 months before she met me she had some casual hookups. One was a virgin but had the biggest cock she ever had. Most of the guys ended up flaking on her for one reason or another, but she had fun and got around.
Anyway, last Monday was when I suggested that we should maybe try a break to see if that improved things between us. Things had been particularly bad for about a week and I thought the space apart would do us both good. Steph was hesitant to the idea at first as she saw it as being the same as breaking up, but she eventually came round. We agreed on two weeks apart, but that we would spend Valentine’s Day together at Steph’ apartment (which fell on Sunday at the end of week one).
Steph and I had barely talked over the first 5 days apart, besides Valentine’s Day morning, arranging when I would come over. I arrived at her front door in the evening and was greeted by a very happy-looking Steph. She threw her arms around me and kissed me deeply, I promptly dropped the bag I was carrying and kissed her back, forcing her firmly up against the door-frame. Steph let out a soft moan while we kissed, and it became obvious that she was already turned on. I assumed that the time apart was already having the desired effect. We headed inside and closed the door.
The room was dimly lit by just a lamp in the corner. Steph asked what was in the bag and I told her it was her Valentine’s Day present. I told her she had to wear it under her dress for the evening. I had bought her a black low-cut bra with red frills and matching panties and black stockings. I knew Steph’s pale figure would look absolutely stunning in it.
Steph said she loved it and that it would look great with the heels that she had bought when shopping with her friend, Lucy, on Tuesday. I asked what else she had been up to and she told me nothing much. Her and Lucy had met up on Tuesday (the day after we had started our break) and went shopping, then went back to Steph’ apartment and drank a bottle of wine each. After telling me this, Steph grabbed a bottle of red wine and poured two large glasses out. After handing one to me, she grabbed the entire bottle and the outfit, leaving her glass, and quickly rushed upstairs to change.
Around 10 minutes had passed, and I was quietly sitting on the sofa watching the news, excited for Steph to return. “Bzzzzzzzzzzzz,” there was a loud vibration that made me jump slightly. I reached over and picked up Steph’ phone from the arm of the sofa. “Bzzzzzzzzzzzz”, her phone went off again in my hand. I turned the screen on, and it read “Chris: 2 New Messages.” I was confused and sat for a moment, contemplating why her ex would be texting her. I was torn between unlocking the phone and reading the messages – which Steph would surely find out I had done – or leaving them. I walked out in the hallway and listened; the shower was still running. I decided I was going to look and sat back down on the sofa. Each attempt to unlock the phone was met with a violent noise and vibration and I quickly realized Steph had recently changed her unlock code even though she never changes it. I carefully placed the phone back on the arm of the sofa in its original position and resumed watching TV – I desperately wanted Steph to return to so I could try to peek at the messages.
“I’m coming down,” Steph playfully shouted from upstairs. This was followed by the gentle, regular thud of her heels on the wooden stairs. Moments later Steph emerged into the dimly lit room and smiled at the look of surprise on my face. “I tried a dress on over this but it wasn’t working. Is it okay if I just wear this tonight?” Steph said, stood in nothing but black high heels and the lingerie I had bought for her.
“That’s great…” I stuttered, now completely forgetting about the texts on Steph’ phone. Steph looked stunning and her E cup tits looked amazing against her curvy figure. Her long, wavy brunette hair flowed down in front of her shoulders and covered the edges of her tits and she had gone all out with her makeup. “You look great” I said while focused on her body; she replied that she just wanted tonight to be special.
Steph was definitely a 10/10 when she made an effort to look good, and she knew it. Steph poured the last of the wine into her glass and sat down ungracefully on the sofa. I noticed Steph grab her phone and remembered about the messages. I expected her to comment on how odd it was that Chris had text her. She unlocked her phone and a smile appeared across her face and she speedily began to type. “Who are you texting?” I asked timidly.
“Just Lucy, she’s asking if we should go shopping again” Steph replied. I instantly knew this was a lie and felt my stomach knot.
I desperately wanted to ask further questions without ruining the potential evening with a very drunk Steph in nothing but her underwear. “…just Lucy?” I asked timidly.
“Yes!” replied Steph, “What are you getting at?”
“Nothing, it’s just that when you were upstairs you got a text from Chris,” I said.
Steph looked shocked for a moment, as if she had been caught. “Well it’s not really any of your business who I talk to when we’re on a break, is it?”
I was stunned and became worried thinking of what she had been doing all week. I stood up and started pacing. After a moment I asked, “Did you fuck him?”
Steph’ heels gently thudded as she walked over to where I was standing. Steph paused when she reached me. We were standing face-to-face. Her heels added enough height to make her almost as tall as I was. “We were on a break and you could have fucked anyone you wanted too,” Steph said. “You were the one that suggested a break so it’s not like I cheated on you.”
“Maybe not, and maybe we should have been clearer about the expectations for this week, but you sure were quick to go out and fuck your ex. I can’t fucking believe this,” I yelled.
“You need to cool it right now,” she said. “I’m going upstairs. You can leave or you can join me when you’ve calmed down and accepted this.”
After 20 minutes of thought and two beers I had made some conclusions. I had partially accepted that I didn’t specify what the rules of being on the break were so that wasn’t completely Steph’ fault, but I was still upset that she would fuck her ex after just days of being apart. I had also calmed down a great deal and was ready to talk. I stood up and began walking upstairs. I got to Steph’ door and as I was about to knock I heard a faint moan from her room, then a slightly louder one. I slowly opened the door and Steph was laying down on the bed; she had removed her bra but still had her panties and heels on. Her left hand was gently pinching her nipple and her right hand was gently rubbing her clit through her panties.
The door creaked as it opened fully, and Steph looked at me. “I’ve decided I need to make it up to you, so you can forgive me,” Steph said gently. She got up off the bed and walked over to me. Her perfect tits swayed as she walked. Steph spoke softly as she reached me whilst gently pinching both of her nipples. “I know what you want; it’s been a week now hasn’t it?”
I nodded and Steph swiftly dropped to her knees. She unbuttoned my jeans and removed my boxers, then held her hands together behind her back. Steph slowly put the head of my cock into her mouth and began sucking softly, not breaking eye contact. Steph then advanced along its length, going slightly deeper with each stroke until she had my full length in her mouth. I let out a moan as Steph gagged attempting to keep it all inside her mouth. The thoughts of anger were now fading due to the beer and having my cock sucked so well. Steph gagged a final time before removing my cock from her mouth. She took her hands away from behind her back and began pinching her nipple with one and rubbing her clit with the other. Steph began licking the length of my cock.
“How can you forgive me if you don’t know what I’ve done?” Steph said innocently. I didn’t know what to say. “Want me to tell you?” Steph said, this time less innocently. Despite still being furious about sleeping with Chris, my cock instantly got harder; we both felt it. Steph moaned loudly whilst licking the tip, “I’ll take that as a yes” she giggled and continued to suck.
Source: reddit.com/r/gonewildstories/comments/ey949d/mf_my_first_time_being_cucked_part_1_of_5