My girlfriend Ivy travels a lot for work and I have unpredictable hours at my job, so we often can’t see each other for long periods of time. After some sexual experimentation with threesome’s we decided to try an open relationship, while she is on work trips. I already hooked up with Cassie, a younger girl, who works in the same building as me.
Cassie looks like your typical, pretty front desk employee. However she turned out to be heavily tattooed (normally hidden under buttoned up business clothes), a hard party-goer and for some reason interested in me. (She also likes it a little rough in bed.) It is pretty hard to pick someone up, especially with my often odd hours. I am not particularly proud of taking advantage of Cassie’s daddy issues or whatever it is, that makes her interested in me, but I am also only human.
Ivy is out of town and had her first hook-up too. I knew she was going out with someone, she finds attractive. I know it is hypocritical, but I am not enjoying the prospect of Ivy sleeping around. I was pissed off and jealous. So I decided to invite Cassie out to keep me company and distract me from the thought of Ivy and another guy.
Cassie is still in college. She only works the front desk to earn some additional money. After a tour through some different locations, we ended up in some bar near the campus, where like everywhere I went that night I was the oldest person around. I felt out of place. Like someone had brought their uncle for a drink. I already had a reason to drink with Ivy out and about to hook-up with someone else, now I had another one. So my distraction strategy worked like a charm.
Cassie introduced me to some of her friends. Well I got the same mix of dirty, disgusted envious and amused looks everywhere. I always seem to get them whenever I am out with her. A thing to get used to I guess. The good thing about keeping odd hours and being out a lot at night for work is, I was able to keep up with the bunch of twenty-somethings I found myself attached too. It isn’t something I would like to do on a regular basis. The one other benefit of being older was, I had a lot more knowledge than during my college days. I could talk to just about anyone there and have a topic to talk about besides sports and the weather. This allowed me to talk to other people without hanging on Cassie all night, looking like some creepy tag-along stalker.
Well that evening I drank slow and a lot less, than the first time I went out with Cassie. The reason being, that the night did start out with me wearing a condom, but in the heat of the moment I did fuck Cassie without one. After things were said and done Cassie took me back to her place and I got the best distraction from Ivy and her colleague.
Cassie’s roommate was out so we had the place to our selves. We sat on her couch. Whenever I am with Cassie, I seem to regress to my teenager days. I can’t remember me and Ivy making out that much. Sure we kiss and there is lots of foreplay, but not that fondling kind of making out, I did as a teenager. However from there Cassie went on to undo my pants and giving me a blowjob. I can say one thing for Cassie, she knows how to give head. I stood up and in front of Cassie and took the opportunity to get rid of my clothes. While I was undressing Cassie kept jerking me and blowing me.
When I was done Cassie stood up and kissed me. Till now we always were at least a little rough in bed. That night Cassie seemed to be in a different mood, so I went with the flow of things too. I kissed her back, slowly pulling up the black print t-shirt dress she had been wearing. I took in the view and I always am amazed at the difference between tattooed college girl Cassie and prim and proper front desk Cassandra. I have to say, I never understood the allure of tattooed girls completely, but on Cassie they are hot.
We continued making out and caressing each other. This time around more like adults than horny teenagers. I undid and removed the rest of her clothing. Taking my time with doing so and massaging her privates, while liking and kissing my way down to the good spots. I could tell the slow warm up had done its purpose and Cassie was ready to continue.
She went down on all fours, positioning herself on the couch to be taken from behind. I got behind her and worked my way into her slowly. This time not forgetting to put on a raincoat. I took up speed in little increments. The build up of speed and Cassie playing with herself had her moaning in enjoyment. She was building up to an orgasm, but when we heard the scraping of keys on a lock, we had to stop and made a dash for Cassie’s bedroom.
Her roommate had come home, with her own hook-up. Well they got an eyeful of us, before we made it to the bedroom. Cassie was huffing in frustration. She had been close to climax and then denied in the last second. So I laid her down on the bed and ate her out. I think by this point a blind man with a roll of sandpaper could have made Cassie climax as aroused and wet as she was. She moaned, she shivered and she came.
The whole situation had given me an idea though. Instead of returning to fucking her I continued to lick her a little more forceful and added my fingers to the mix. Cassie was enjoying herself, laid back on the bed. But shortly before she could finish again, I stopped. After a moment I started right back up pleasuring her, but stopping short of giving her an orgasm.
At first she looked at me in bewilderment and I got another set of frustrated huffing. But then she understood what I was doing. I was intentionally denying her to build anticipation and pleasure. I continued that until she practically begged me to finally make her orgasm. She was moaning and whimpering in frustration and pleasure, and I was amusing myself smiling internally about this completely different side of Cassie, who had till now only shown me she liked it a little rough.
In a story this would be the point where I tell people, that she came as soon as I plunged my 15 foot pole into her and she came screaming like a banshee. Well she did come screaming like a banshee. But I don’t have a 15 foot cock and it was only I properly got on top of her and we had sex in the good old and boring missionary position. After a minute or two of fucking Cassie finally found release.
Cassie pulled up her blanket or was it a small pillow. She bit into it, trying to keep quiet. But after a few fruitless moment, she screamed out her pleasure. Loud enough for her roommate and the other guy to hear. I am mentioning this, because a few minutes later we could hear them fucking and climaxing. Apparently they didn’t want to be outdone by horny Cassie and the old fart.
At this point Cassie was spoiling for two things. To get even for the teasing treatment I had given her and to show her roommate and the other guy how things were done. Cassie, still sensitive from her recent orgasm, had me lay on the bed and mounted me literally. She got on top of me and my cock. She kissed me and started riding me. My role in this was human sex toy nothing more.
Cassie played with her clit while riding me. She just wanted to make herself climax as fast as possible. So I decided to relinquish my passive role and gently massaged and rubbed Cassie’s other sensitive areas, her breasts and nipples. It worked. Within minutes she was climaxing again, or doing a very convincing job at faking it.
Then she got down from me and removed my condom. She started playing with my balls and cock. She sucked, licked, massaged and jerked me. Not necessarily in that order or only once. But only within an inch of my own release. Well she kept doing that until I was practically begging her to finish me off. Cassie ended the night by catching my load with her mouth, while I had one of the biggest orgasms in recent history, or so it felt.
Source: reddit.com/r/gonewildstories/comments/9non65/dating_a_younger_woman_mfopen
That was really hot. I’m looking forward to more of your stories.