This story is sort of a continuation of my first story about my girlfriend Steph (29), so if you want to get the full context, go back and read my first post if you haven’t already.
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If not, here’s some background. One night back in college after a night out at the bar, Ryan (Steph’s boyfriend at the time) convinced Steph to have a threesome with him and his roommate James. With some skepticism, she agreed to suck James’ dick but not fuck him, so they ended up spit roasting her with Ryan fucking her while she gave his friend a blowjob. The next morning, Ryan regretted his decision, became territorial of Steph and it ultimately lead to them breaking up a few months after. Steph had little to no communication with both Ryan and James for the remainder of college.
Years later when Steph graduated, she moved back home to her parent’s house. One night when she was swiping on tinder, she came across James profile and they matched. She didn’t think much of it other than a friendly gesture, so they greeted each other, made some small talk, found out that they lived just 10 minutes away from each other and she pretty much went about her day as normal.
About a week or two later, she coincidentally ran into James at the gym. They had both finished their workout and so James asked her if she wanted to grab a drink and catch up and she said yes. They went to a nearby bar where they talked and ended up having a few more drinks than they had planned. After they left the bar and were talking outside of Steph’s car, James leaned in for a kiss. They made out for a bit and before they knew it, James had Steph on her knees giving him a blowjob in the backseat of her parents SUV.
Things got heated very quickly. James laid her down on the seat, took her clothes off and started going down on her. After he made her cum, he mounted her and while making out with her, she could feel him sliding the tip of his dick up and down the outside of her wet pussy. Knowing what was about to happen next, she asked him to put on a condom. He told her he didn’t have one with him, but said that he’d pull out. Steph initially said no since she wasn’t on any birth control at the time. On top of that, apparently James had a huge dick (around 8-8.5 inches and girthy) and Steph had never taken a dick that size before and was scared it wouldn’t fit. James was persistent though, and he eventually convinced her by saying he’d only put the tip in for a few strokes and that’s it. Steph was too horny and drunk by this point and gave in but told him he had to go slow.
Of course, it didn’t stop at a few strokes and “just the tip” quickly turned into her taking almost the whole dick, to her surprise. He did go very slow as he promised, but still managed to make her cum a second time within a few minutes and at this point, he had her legs weak and shaking uncontrollably.
After about 5 minutes in missionary, he asked her to flip over into doggy. Steph, still weak from her orgasm, knew they were getting carried away and told him they had to stop, but that she’d make it up to him next time when they had a condom. Instead, she sat him down and finished him off with a sloppy blowjob and swallowed his entire load.
This night was the start of their 3 month long “situationship” before James got a job in a different continent and moved away. Most times, they would meet at the gym 3-5 times a week, workout together, and then park at a nearby warehouse parking lot and fuck in the car, often times going for multiple rounds. Once in a while, Steph would message James and tell him she was wearing a skirt to work, which meant she wanted him to come fuck her during her lunch break.
Since they both lived with their parents at the time, the majority of the times they would fuck would be in a car at any hidden location they could find. However, on two occasions, her birthday weekend and the weekend before James moved away, they booked a hotel for the entire weekend and basically had sex all day or until Steph tapped out.
Also on both of these weekends, on the last night of their stay, she let him fuck her with no condom, cum inside her and then took the Plan B pill the next morning.