I finally [f]ooled around with my handso[m]e older friend/former boss.

I first met Chet 5 years ago at a work related event at a bar. I was a cute little 24 year old in ripped tights and a short dress, and he was a very handsome 40 year old man, well dressed in a casual suit. We chatted for a bit while I smoked a cigarette, thinking I was being so charming and adult, and we’ve been friends ever since.

Im tall, long legs, a bit of a belly but nothing crazy, perky smallish boobs, long dark hair and a pretty face. With these features I’m certainly not everyone’s type, but the guys who are into it think I’m hot haha. I’m in a creative field and am used to hooking up with guys who are like me, grungy and disheveled, which I love! But Chet is different, an executive at a financial company, he wears suits and nice clothes, combs his full head of thick gray hair back and parted, and he looks a lot like a less-heavy Alec Baldwin in 30 rock. It drives me crazy. The first few years I knew him it was as a casual friend. He’s interested in my creative field and would show up to lots of my work related events to drink with me and my friends in the same field.

Now, Chet is married and I have a boyfriend. This has been the case for all 5 years of our friendship, and I’m not proud of any of this, which is why nothing happened for 5 years until the attraction and tension got too much to bear.

A couple years ago he started a business/project that relates to my field and hired me to help him learn the ropes and get it all set up. It wasn’t a full time job or anything, just a friendly help once in a while. We became closer friends during that time but I never thought he returned the attraction I had always felt for him. We would flirt while tipsy over the course of our friendship but I never thought much of it on his end since he was a pretty big flirt with everyone, and really, so am I, so he never suspected my crush either. While working on his project I would often see him more dressed down, in jeans and t-shirts, and he was just as sexy like that. I started to feel like I couldn’t keep my crush secret anymore, and would fantasize about making a move on him, but would always hold back because he was married. He started inviting me out for drinks just the two of us for work meetings, and I noticed he would slyly touch my lower back or thighs/hips while walking past me. Whenever he did that my heart would skip a beat and I would get so turned on. I still wasn’t sure how he felt about me, but at this point I was just being overly cautious, since it was becoming obvious that he was at least attracted to me.

One night, during one of these meetings, we both got pretty tipsy and started talking about sex and relationships, just being bawdy and friendly, not some serious heart-to-heart or anything. I told him how my boyfriend and I were in a fairly open relationship and suddenly his eyes got wide and he got very animated and started asking lots of questions. He said he was jealous of it, wished he could have that in his marriage, talked about how he hadn’t had sex with his wife in a couple years, and asked me what guys that we knew that I would be allowed to, and want to, hook up with…

I paused after that question for a few beats too long and just had a stupid open mouth smile on my face. I knew that was my opening to say something to him but it still felt too forward and embarrassing. But with my liquid courage I stammered out a couple names of mutual friends, and then an “uhhhh… and… you….”

The look on his face was priceless. Pure shock and amusement, and I still couldn’t read if he felt the same. “you would want to hook up with me..?” And I just kinda nodded in response. Well, the floodgates opened and he admitted that basically every interaction we had over the years was him trying to get closer to me, starting with the first time we met. I thought we just happened to be standing near each other so started chatting but apparently he sought me out to talk to me. He just had no idea I was so attracted to him too. So now everything was out in the open, and all of our past interactions made much more sense.

Our friendship changed a lot in this last year after that talk. I still didn’t want to be a home wrecker but our flirting became overt when we were alone since there was no pretense anymore. Once at an event a pulled my shirt down to flash him when we were in a hidden corner and he had to stay hidden for a few minutes after I walked away because he got immediately hard. I knew he was having side flings during this time as well, which made me feel less guilty but I did (and still do) want to try to live by some sort of moral code. It’s just hard to be good.

But last night I couldn’t resist anymore. We were drinking at my house with some friends until everyone filtered out, my boyfriend went to pass out in my room, and it was just me and Chet left. He didn’t waste any time once he had me alone and walked up close to me while I was leaning on the couch and gently put his hands on my hips. My heart was pounding and the last bit of my moral strength sapped out of me when I noticed through his pants that he was already rock hard and fairly big. We went from laughing and joking, to locking eyes. I gave a small nod and he pressed his body into me and slowly met my mouth with his his lips in what started as one gentle kiss, then became a passionate make out. He is an amazing kisser. Both gentle and strong, confident and caring in the way older men can be that makes me melt and feel like the innocent young girl that I haven’t been in years. He rocked his hips up against me, grinding his hard cock against me, which is one of my favorite feelings in the world.

We pulled apart and he said that he couldn’t believe he had thought about that for so long and it was even better than he imagined. (What a line, right? I ate it up though.) I nibbled on his earlobe as he pulled my shirt down and started playing with my tits, alternating between sucking on each little pink nipple and massaging the other breast.

I pushed him down onto the couch and unbuckled his belt. He pulled me up to roll around and kiss more, while taking that chance to pull my clothes off while I pulled his shirt off. He was a lot hairier than I thought and loved that. I was dripping wet at this point and his hand made his way to my warm, throbbing wet pussy and started to finger me while we kissed. At this point, he wanted to have sex with me, and this is probably the one not-terrible decision I made last night, because as much as I wanted nothing more than for him to be on top of me, to feel him push himself inside me, we didn’t have a condom and I felt like full on sex wasn’t a good idea. So I pushed him back up to a sitting position on the couch and moved down onto my knees. I finished undoing his pants and pulling them down and freeing his cock.

His cock looked amazing, fairly big, normal girth with a big head, and so, so hard. I just stared at it for a few seconds with a sly smile. I grabbed him at the base with one hand and gently pushed up on his balls with the other, and started teasing the head, licking and kissing it. But even I couldn’t hold off too long doing that and started lowering my head slowly down his shaft to take him all in.

After starting slow, I began to greedily swallow and bob up and down his cock, using my tongue to twirl around his cock’s head in my mouth, using my hand at the base and getting spit everywhere, dripping down his balls. I kept looking up at his face, his sexy blue eyes, and the soft moans coming out of his mouth. At one point I grabbed his hand and put it on the back of my head so that he could control my rhythm, which he did and after just a minute or so of that I started tasting some precum. I looked up and smiled while blowing him because I’ve always wanted to taste his cum, I’ve thought about it so many times, and now his cum was in my mouth! He started pushing my head more firmly and quickly and I happily obliged, sucking harder and harder, begging for his cum, until I felt him raise his hips and explode inside my mouth for what seemed like a full minute with tons of salty cum that I immediately swallowed several times while he moaned. We were trying to be quiet but his groans that escaped were the sexiest thing I’ve ever heard.

Afterward he told me that he hasn’t had a blowjob in years, and hasn’t cum from one in even longer. I crawled back up and we made out for a while longer, and he lazily fingered me some more while we kissed, but he had to leave pretty quickly after that.

Unfortunately, as much as I want him to be inside me, to pump his cum inside my wet pussy, we can’t do it again. My boyfriend doesn’t want it to happen again and I don’t want this to escalate. I told him that we were just releasing years of sexual tension, but that’s a lie, now I’m even more attracted to him. knowing how strong but gentle, manly and sexy he is, I want his cock even more. Oh well.

Source: reddit.com/r/gonewildstories/comments/5yh3zb/i_finally_fooled_around_with_my_handsome_older