My [M] virgin Asian coworker [F] Part 2: What to do when it won’t fit

This is a continuation of the real story about the sexual awakening of my virgin coworker. Another pic is below.

Picking up where I left off, my coworker came over that same night. She told me that the night before she hadn’t wanted to take her pants off because she was embarrassed about her bush.  But now she was waxed for the first time in her life.

Later on I came to learn she grew up in a very conservative house, and her parents still forbid her from dating even though she was in her mid-20s and lived on her own.  They said once she went back to graduate school and had a real career (more than just an office assistant) she could date and get married.  But she finally decided she had enough, although she didn’t tell them that. She was ready for her first time, and I was in the right place at the right time. 

We made out again, with our hands all over each other.  I undid the button on her pants and slid them off.  My mind was blown as I realized under her baggy clothing she had been hiding an absolutely incredible ass.  If you saw the picture on the first post you know she has a big round butt for such a tiny woman.  I grabbed and squeezed it with both hands.  She pulled her panties down to reveal her small, freshly waxed pussy.  She lay her fully naked body down on my bed and spread her legs for me.  I spread her lips, slowly put my middle finger inside her wet pussy, and she grimaced.  It felt like a vice on my finger.  She had never masturbated before and almost always used pads, not tampons. 

I went very slowly and she relaxed enough to start enjoying it.  But it was only one finger, and I was only going two knuckles deep.  After a while she said the words I was waiting for.  “Put it in.”  I threw on a condom and an entire fistful of lube, then pressed the tip of my rock hard cock up against her tight pussy.  I pushed and… she screamed and clamped her legs shut.  There was no way it was going in.  We tried over and over, but no matter how much lube we used and how relaxed she was, the laws of physics prevented it from happening.  We spent the night touching, kissing, and dry humping, and she ended up using her little hand to jerk me off into a towel.

Over the next few weeks we kept secretly hooking up after work.  Lots of hand jobs, her first awkward attempts at giving head (thankfully she’s a fast learner and quickly figured out how to get her teeth out of the way), more fingering.  And more failed attempts at sex.  She loved lying on her back while I got on top of her in missionary and rubbed my penis along her pussy (she called it “practicing”).  She also talked to friends, did some research, and ordered a set of vaginal dilators [like these](https://www.amazon.com/Intimate-Rose-8-Pack-Silicone-Dilators/dp/B07BKB4NR9/ref=sr_1_7?keywords=vaginal+dilators&qid=1666290193&qu=eyJxc2MiOiI1LjU5IiwicXNhIjoiNC44NiIsInFzcCI6IjQuNTAifQ%3D%3D&sr=8-7) – basically little training dildos.  She was going to use them until her tiny pussy was open enough to take me.

Our fun was interrupted by a trip she had previously scheduled to stay with her parents for a month and work remotely.  She vowed that she would spend the month using the dilators and be ready for me when she returned.  But things got more interesting than just that.  The first weekend home, she went on a ski trip with some old high school friends, both male and female.  After drinks, one long-time and very nerdy friend confessed that he had always had a crush on her, and he asked her out.  She rejected him.  She texted me about it afterward and based on her description of him I felt bad for the guy, so I half-jokingly suggested she could at least give him a pity handjob.  To my surprise, she instantly agreed.  About 30 minutes later she messaged me that she had gone into his room to talk through things, offered to touch it, and ended up stroking his small penis until he ran into the bathroom and came in the toilet.  This must have turned her on like crazy because she told me there was another friend on the trip who she wanted to try the same thing with – a good-looking guy who was kind of a jock.  Early the next morning she crawled into his bed and woke him up by asking if she could give him a handjob.  She said his penis was much bigger – about my size – and he acted very proud of it.  He came all over the floor and she cleaned it up with some towels from the bathroom.   

She spent the next month back home getting her two friends off almost every day.  Over the month, the handjobs evolved into practicing her sucking technique, which was light years better when she returned.  She saw the guys one at a time but, being in the same friend group, they knew about each other.  One of them was jealous, the other didn’t care (you can probably guess which was which).  Of course they wanted to touch her and do more, but she made clear she wasn’t ok with that – she just wanted to get more experience making men cum.  During the day she hung out with them (her parents didn’t suspect anything since the guys were old friends) and at night she practiced using the dilators.  By the end of the month she could comfortably take up to level 5.  I’m a bit bigger than the level 8 in her set, so we weren’t sure whether it would work when she got back.

She came over right away on the day she got back – after a month apart we were both crazy horny and so eager for her to experience her first time.  I wish I could describe some wild porn star sex where I blew her back out and made her cum over and over, but it wasn’t really like that.  She was so, so tight, but this time my cock made it inside her virgin pussy.  It gripped me like nothing I’d ever felt before.  I was on top of her in missionary and went as slowly and gently as I could, but her face showed how much she was struggling to take it.  Her head was back, eyes tightly shut, and her hands balled up into fists.  I worked up to a faster rhythm and was going about half way in on each stroke.  Finally I couldn’t take it anymore and whispered in her ear, “You’re making me cum” as I filled the condom inside her tight pussy.  Afterward she said it felt good but painful at the same time. 

She was emotional after, as should be expected from her first time.  But she liked getting fucked, and she quickly got used to it.  The third time we had sex she had the first orgasm of her life, cumming on me as I gave her the entire length of my penis.  It would be the first of many, many times she came on my cock (including one time when she had ten orgasms from sex within about 30 minutes).  We got very wild as she made up for the delayed start to her sex life.  I’ll save some of that for the next part.

[Here’s a verified pic from this weekend](https://imgur.com/a/8kaAYqR)

Source: reddit.com/r/gonewildstories/comments/ycks9i/my_m_virgin_asian_coworker_f_part_2_what_to_do