I dated Penelope for six years. She was my high school sweetheart, and we’d both been each other’s firsts. Our sex life had always been tender, almost innocently bland. Neither of us had explored much, we were both on the shy side and all we ever tried was vanilla.
Free cuckold community
Sign up now!
One day, while abroad, perhaps driven by some spring lust, I asked her if she had ever thought about open relationships. She was stunned, and replied that she wasn’t interested. A few days later, she told me the question had hurt her. She said she needed space and suggested we take a break.
I was devastated. I was deeply in love with her and couldn’t stop fearing it was the beginning of the end. She was smart, funny, and kind. Her face had a delicate charm — sparkling eyes and soft, full lips. Her body was like a shrine: she always wore loose blouses that hinted at the curve of her breasts, and dresses that hugged her figure just enough to turn heads wherever we walked.
We were in limbo for about four months. I didn’t sleep with anyone during that time. We met for coffee a few times, but never really talked about the state of our relationship. She avoided the topic, or made clear she didn’t want to talk about it.
One evening as I left work, she asked me out for a drink. It was a last-minute thing, and an inconvenient day for me, but since it was the first time she’d initiated anything, I agreed right away. We had two beers, one thing led to another, and we ended up back at my place.
Things escalated quickly. We’d kissed several times on the way and as we crossed the door, I told her I wanted to eat her out.
Undressing her felt sacred. Like I was touching something I had been barred to see. She didn’t let me take off her top. She wore black lace panties I hadn’t seen before.
I slowly pulled them down and realised they were soaked. I knelt and slowly skimmed my nose on her mound. Her lips were opalescent. As my tongue lightly went up her inner thigh, she gently pushed me back, as if she had changed her mind. I tasted her anyway, and she pushed my head back again. I looked at her, and she asked if I was fine in a worried way.
I didn’t reply and buried my face between her thighs, and didn’t part from her until her legs started to give up. After some time, she trembled for a few seconds, and grabbed my hair. I looked at her as she caught her breath. She asked if I was sure I was fine. It startled me. I couldn’t tell if she had climaxed, and wanted to slide my tongue in her again but she pulled her panties up ans immediately began to get dressed. She didn’t seem interested in cuddling or lingering. As she dressed up, I asked if something was wrong. She said that everything was fine, and that she’d had a great time.
She headed toward the door, and I followed. I wrapped an arm around her waist and tried to kiss her again, but she turned and said:
“I’m sorry, I’d love to do more, but it’s late and I need to go back home…”
I asked if she wanted to spend the night. She hesitated. Something was off. I stayed silent. She looked at me with a pained expression before saying:
“I’m sorry… I think I should have told you before but I’ve been seeing someone else.”
I knew instantly that she was telling the truth. My heart sank. I couldn’t stop myself from asking if I knew him. I asked, but she wouldn’t say. It felt like she was hiding something. I asked what they’d done, and though she didn’t answer, her silence was confirmation. It was clear they’d slept together. I remembered she’d traveled to Belgium with friends a few weeks earlier and asked if it happened there. She seemed confused, even slightly mocking, and said no. When I asked if the break had been for this, she got visibly upset. She reminded me that I was the one who’d brought up the idea of an open relationship. I told her I regretted my words. She didn’t reply.
Her irritation was showing. She opened the door, and just as she was stepping out, she turned to me and said:
“I was actually with him this afternoon. I meant to tell you over a drink, but I couldn’t… coming here tonight was a mistake.”
I was speechless. She left.
It took hours for everything to sink in. At first, I was crushed. But sorrow soon turned into frustration. By the time I got into bed, all I could think about was that another man had been inside her. We were no longer exclusive, and the innoncence of our relationship was stained. That night, I couldn’t stop picturing him inside her. The way he must have touched her. The way she must have felt as he entered her.
What tormented me most was knowing she had seen him right before coming to me. I didn’t think they’d had sex that very afternoon, but I couldn’t feel certain. Seeing him again surely meant she considered starting something with him.
I didn’t sleep.
A few days later, I texted her, asking to talk. She agreed. We met at a café and circled back to the topic of open relationships. She chuckled at how the roles were now reversed. She said she hadn’t seen the guy again, which gave me a sliver of relief. She said there was nothing between them, but that it didn’t mean there would be something between us again. I couldn’t resist again and asked:
“Can I know if it was someone I know?”
She hesitated, but refused to answer. Her silence was cruel. We moved on, and I asked if, since we were uncertain about our future, we could be friends with benefits.
To my wonderment, she said yes. Yet, knowing she had been with someone else and I had not was humbling. She was picking her sister at the station that night, so we parted with a brief kiss. Although hopeful, I was still obsessing over the idea of someone else thrusting into her, seeing the pulses of pleasure on her face. I wondered what I was doing at the very moment she was giving herself to someone else.
A few days later, she came over. I undressed her slowly. She was wearing my favourite pair of panties. I went down on her for a few minutes, and we soon moved to the bed.
Then she asked, “Do you have condoms?”
The question startled me. We hadn’t used protection in two years. I said I didn’t, and couldn’t stop myself from asking why she’d brought it up. I asked if she’d been with the other guy without protection. She hesitated, then said:
“I got caught in the moment… I thought you knew.”
The mood crumbled. She started getting dressed again. Noticing my new keyboard, she asked if I was taking piano lessons. I said I was planning to.
Then, she gave me a look filled with guilt and shame. She could tell I was confused. Her look pierced like a blade. Her cheeks flushed red and she said:
“When you went down on me last time, I thought you had noticed I’d been with someone else. I was thinking you would have stopped right away, but you didn’t say anything.”
I was stunned. I asked how I possibly could have known.
She looked away, and answered softly:
“I don’t know… I thought it was obvious for you.”
Silence fell between us. A thick, uncomfortable silence. I felt a rising fury. I couldn’t be certain of what she meant, but inside me, I knew.
I couldn’t tell if I wanted to scream or just fuck her again. I wanted to be the one who had been inside her last. I asked if we could do it without a condom. She seemed confused I asked for this, declined, and left without a word. A few minutes later, she sent me a text:
“I’m sorry about doing that you.”
That night, my mind spiraled. I replayed the night I saw her again and again. I imagined every second of her day.
Her lace panties for him. Her trimmed bush. The second he entered her surrendering body. And then later her taste. The way she barely climaxed. The way she left. That her wetness hadn’t been arousal. It was him.
I wanted to ask her if any of it was intentional but was too embarassed to do so. Had she come to me that night not out of confusion or longing, but with the quiet, deliberate cruelty of someone exacting a punishment? Perhaps she hadn’t meant to tell me over a drink. Maybe she wanted me to find out someone had just been inside her.
We exchanged a few texts after that, but only saw each other twice. Once, to get my belongings. And once, two years later, at a friend’s wedding.
I hadn’t slept with anyone in the meantime, and I knew she was single before going. I fancied reclaiming her for weeks.
We glanced at each other a few times during the ceremony. I was two rows behind her, and her backless dress plunged me straight back in the memory of her arching on our bed. Her plugning neckline left no doubt that she had gained confidence.
As the party went roaring, we drank, danced, and gave one another flirtatious looks. At one point, we snuck into a quiet corner. I asked her how she was doing. She didn’t reply and kissed me. I rest my hands on her breasts a few fleeting seconds. The tenderness of her chest immediately got me. It felt like quenching a thirst I had held onto for months. She hid a giggle and gently drifted my hands away. Her gestures left no doubt that her body was off limits to me.
Later, I saw her kiss a guy in a corridor. As the night ended, I went to talk to her, hoping she’d consider talking, but I saw her waiting at the coat check with the same guy. They were drunk, and his hand was openly groping her, sliding with quiet ownership accross her lower back. Our eyes met. She blushed. And left with him.
Back in my room, I got in bed and imagined them together. I knew she was just a few meters away, in another room, perhaps behind the wall. Yet I couldn’t know if he had already undressed her. I was wondering if he was inside her at that very moment. It felt as if I could stop it. But I didn’t. I kept picturing what I’d missed again: holding her hips, the smell of her clothes, her voice muffled in the sheets. Another man was defiling her body, and I was left fantasising about inadvertenlty brushing against her breasts. I wondered how many men had slid their fingers under her panties while she was still the only one I’d known.
I hated the thought. And still, I kept circling it. It wasn’t just jealousy. It was something else. Something harder to name, something she had poisoned me with.
When I saw her at breakfast, smiling innocently as our eyes crossed, her hair still wet from the shower, her skin freshly covered with mist, it made sense. I didn’t just miss her. I missed the slow ache of watching her slip away. The exquisite cruelty of losing her.