This happened about 10 years ago, I was 24 and in a long distance (very) open relationship at the time. Open to the extent where I told her about my conquests and she only got turned on from them.

I had a very close female friend, let's call her Romy, she's Belgian, short and tiny, long brown hair, deep brown eyes. We hung out twice a week, very platonic at the start, but we talked about everything and everything. Especially when we were drunk.

This is about one such night, and the four months that followed. We were watching some silly movies, got very drunk, and started talking about sex. I shared about how submissive my girlfriend was, how she was a bit of a cuck too, and we laughed, then I asked her about her sex life. She got very cagey all of a sudden, so I asked her: "You're not a virgin, are you?" She awkwardly looked away and said "I... Not quite, can we not talk about this any more?"

I let it go, and we went back to selecting a movie. We put on No Strings Attached (a mediocre Ashton Kutcher romcom), but after 10 minutes she paused it. "So, I'm not a virgin, I've had sex once, but it hurt too much, so I haven't really tried it since."

My girlfriend at the time had actually had a similar issue before meeting me, and went to the doctor, who helped. I asked Romy if she had gone to the doctor. "No way, I can't do that, that's too embarrassing." I told her I knew someone who went through the same thing, and I could ask her what helped for her. I asked my girlfriend, and she recommended three things, talking to a doctor, kegel exercises and dilators. I relayed the message and forgot about it.

Two weeks later, Romy shows me, that she got the dilators, a set of seven. She asked me if I could stay with her when trying it. She was wearing a long dress, and wanted to hold my hand trying to insert it. I agreed, and in a way, this part was quite wholesome. She lubed up the smallest dilator, and held my hand as I turned my back, she squeezed it when it hurt, and after 10 minutes, we went back to watching movies.

After a few times, I stopped turning my back, but she still hid behind her dress, so we just watched movies while she moved the dilator in and out softly. Then one night, she was just wearing a pink tanktop and skinny jeans, instead of hiding, she just took her trousers off, grabbed my hand, and started using her dilator. It didn't feel sexual at the time, more clinical almost. Sometimes she'd moan a bit, sometimes in pleasure, but more often in slight pain. I did notice her big bush, she even commented on how messy her hair was.

When she moved up a size, she said she couldn't do it, and asked me to instead. At first, this didn't feel sexual at all. She'd tell me when to stop, I'd move it around until it hurt. This went on for a while, until one night, she'd completely trimmed her pubic hair. This changed everything for me. All of a sudden, I could see her spread her pussy as I pushed the dilator inside, at the end of a size, I'd push it fully in, and softly rest my hand on her pussy lips. After every night, I would go home and jump on the webcam with my girlfriend.

After about 4,5 have months, when I opened the door, Romy proudly entered "I have something to show you!" She had the biggest dilator with her, took off her trousers and pushed it fully in, and proudly proclaimed 'No pain, at all!' She was wearing nothing but a black tanktop, she pushed it in and out a bit, to show off. Then she became self-conscious. She pulled out the dilator and closed her legs. "I guess that means we should find a different hobby, huh?" She chuckled.

I put my hand on her shoulder and said how happy I was for her. We hugged, but instead of releasing the hug fully, she kissed me. "I've been thinking, I want you to be my first." I bit my lip and thought about all the times I imagined her saying that. Then I said to her "I don't think that's a good idea." "Why not?" I looked at my half-naked friend and stood up. My dick was already hard thinking about it, and when I showed her my cock and said: "This is why."

She was shocked for a moment, but then stood up, and put her arms around me, looked me in the eyes and said "I have lots of lube, and I'm on the pill now." My hands were on her hips now, my dick firmly pushing against her tight stomach, slightly under her tanktop. "You know I have a girlfriend, right?" "I just want to borrow you." I lifted up her top, revealing her tiny tits. My girlfriend was voluptuous, physically the opposite, everything about Romy was tiny. Both were so gorgeous though.

My hands slowly travelled her body "you're the first person in nine years to touch this body, you know." She turned around and I grabbed her neck from behind, I softly ran my fingers up her thighs, and spread her pussy, she moaned loudly as I found her clit. I quickly made her cum with my hand, she grew weak, but I caught her, and brought her to my bed. I put some lube on my cock, and spread her legs. "Are you sure about this?" She put some lube on her hand, grabbed my dick and rubbed it. "Now I am."

I slowly pushed my cock inside her, going slightly deeper with every thrust. She was tighter than any pussy I'd ever felt. I was very gentle, and she took it all in, but when I was fully in, I felt like I was ready to explode. I told her that I wasn't going to last long, her reply was "that's okay, we'll train you next." Then she kissed me. I told her to play with herself while I was still inside her, "I want to feel you cum". I watched her whole body tremble while I felt her tighten even more on my cock.

I thrusted inside her a few times, but to be honest, not a lot, I finished inside her so quickly that first time... She stayed over that night, and I woke up to her sucking my cock. I stopped her and I told her I felt bad for not texting my girlfriend, and she told me not to worry, she'd texted her. When I checked my phone, I saw a message from the gf "Heard you had fun ;);)" I took a picture of Romy kissing my dick and replied "had?" She replied: "Fuck, wish that was me rn."