Straight Female / 24
Work Orgasms
I started working where I am now at 17. I wasn't sexually active then and wasn't for awhile. I've only had a few short relationships but I've always been a horny girl. I made a comment to my boss once back then about a boyfriend and we talked about how he didn't know what to do sexually. He gave me some advise that didn't really work out and we didn't talk much after about it. I went to school, worked part-time in the summer and now I'm a full-time book keeper and data entry person.
I had a few more sex based conversations with my boss who was more open to those discussions than he was when I was younger. He openly questioned what was going on with the guys I dated because I told him that they couldn't make me cum. I've been open with him told him how I was a walking horny hormone all through high school, how I was wet all the time, how I really didn't know how to get myself of or how to show a guy how to. I masturbated but my orgasms were empty, like nothing happening, not real.
We talked a lot and I found myself very curious. I guess it's natural but I started thinking about him. Instead of just advice why not just let him show me? Or do me or whatever.
I said to him, "I wish there was an older guy like you who could just text me through an orgasm." I opened the door and he walked through. He said if I didn't find it too awkward, maybe he could help me.
Yes please lol.
So we started texting at night. I felt guilty because he is married but it was just texting. He made me promise to do exactly as he said. I was in my room, parents downstairs thankfully. I locked my door and got naked. He made me start by massaging my boobs, twisting my nipples, gently rolling them and pulling on them for a long time. He made me feel myself all over. Made me look at my pussy, split it open, run my fingers up and down and rub everywhere but my clit. Then he had me finger myself, then had me look around the room. He had me describe things. He settled on my hairbrush. It was embarrassing but I was so horny I did what I was told. I slid the handle inside myself and slowly fucked my pussy with it following his instructions.
It felt so good but then he made me suck my own tits, then slide my fingers inside my pussy and taste myself, over and over. I was in physical pain I needed to cum so bad. Then he walked me through how to rub my clit, at first just wetting it and circling it, slowly, always so slow, it felt so good but so frustrating. He had me roll onto all fours, reach behind and fuck myself as hard as I could with the brush handle with one hand and rub my clit with my other. It was amazing but he made me stop.
He gave me a minute. I did it and could feel an orgasming coming but stopped like he said. Then after a minute started again and stopped after 50 seconds. Then again and stopped after 40. I was so close each time. Then he said one minute and I fucked myself raw and rubbed the fuck out of my clit and then I felt everything tighten up, and it felt like I was going to piss myself and I came, for real, I came so hard and long, it felt like my insides just drained out of my pussy. I realized that I'd never actually cum before.
We kept going. He made me cum twice more. I never felt so good all that pent up frustration was just gone.
We played a lot at night after that. He would instruct, I would get off. We got daring. He made me cum in dressing rooms, in my car stuck in traffic with a cop ten feet away, at my cousin's wedding, I was cumming all the time. I was like a new person. It was all so new and exciting.
I started to play back, sending him pics of my tits and giving him text blow jobs til he came. He sent me pics of his hard dick and videos of himself cumming. Then I sent him pics and videos of my pussy and of me cumming.
Work was getting tense. He's an older man, he's in his early fifties, I'm 22, he's married but I wanted him to fuck me. I wasn't in love but I was in lust I think. I looked at his dick pics and his cum videos all the time and fantasized about sucking him and him fucking me and cumming in me.
I made it clear if he wanted he could fuck me. He wasn't sure. I obviously turned him on. We were alone and he used his hand on me to make me cum, he was the first guy who ever made me cum it was glorious. I took his dick out, went to suck it, he said use your hand, I did. he wet it and I stroked it while he used his hand again. I came hard and when he was ready I opened my mouth and he put his dick in my mouth at the last second and I sucked him off at the end and I got a mouthful of cum.
He was upset he cheated. I understood and took a step back. A month later we were alone after hours and he asked me how it was going, I was frustrated and soon my pants were off and he was eating my pussy and fingering me, what the fuck it was amazing. So many orgasms.
Then he fucked me and we came together. After a bunch more fucks over the next few months he asked me what I thought. I was clear-I told him I just wanted him to fuck me or eat me, to make me cum but nothing more.
We both did feel guilty about his wife. She was nice and I was an asshole for fucking her husband, it would have killed her to find out. We fucked a few more times then I met a guy, went on a few dates and had sex and kept dating. At first it wasn't great but it got there then it was better. Actually being with the guy was so much better overall.
Me and my boss just naturally stopped everything when i got serious with the other guy. He missed me and felt loss but I think it was a relief for us both. I still have the pics and videos of him and check them out now and then and I still re-read some of our text threads to get myself off he was amazing. I hope he does the same.
And what he doesn't know was that he took my virginity with a hairbrush then took my actual virginity on the couch in his office. My boyfriend thinks he was my first because I didn't know what else to say but it was really my much older married boss. I think that'll be a secret forever.
I had a few more sex based conversations with my boss who was more open to those discussions than he was when I was younger. He openly questioned what was going on with the guys I dated because I told him that they couldn't make me cum. I've been open with him told him how I was a walking horny hormone all through high school, how I was wet all the time, how I really didn't know how to get myself of or how to show a guy how to. I masturbated but my orgasms were empty, like nothing happening, not real.
We talked a lot and I found myself very curious. I guess it's natural but I started thinking about him. Instead of just advice why not just let him show me? Or do me or whatever.
I said to him, "I wish there was an older guy like you who could just text me through an orgasm." I opened the door and he walked through. He said if I didn't find it too awkward, maybe he could help me.
Yes please lol.
So we started texting at night. I felt guilty because he is married but it was just texting. He made me promise to do exactly as he said. I was in my room, parents downstairs thankfully. I locked my door and got naked. He made me start by massaging my boobs, twisting my nipples, gently rolling them and pulling on them for a long time. He made me feel myself all over. Made me look at my pussy, split it open, run my fingers up and down and rub everywhere but my clit. Then he had me finger myself, then had me look around the room. He had me describe things. He settled on my hairbrush. It was embarrassing but I was so horny I did what I was told. I slid the handle inside myself and slowly fucked my pussy with it following his instructions.
It felt so good but then he made me suck my own tits, then slide my fingers inside my pussy and taste myself, over and over. I was in physical pain I needed to cum so bad. Then he walked me through how to rub my clit, at first just wetting it and circling it, slowly, always so slow, it felt so good but so frustrating. He had me roll onto all fours, reach behind and fuck myself as hard as I could with the brush handle with one hand and rub my clit with my other. It was amazing but he made me stop.
He gave me a minute. I did it and could feel an orgasming coming but stopped like he said. Then after a minute started again and stopped after 50 seconds. Then again and stopped after 40. I was so close each time. Then he said one minute and I fucked myself raw and rubbed the fuck out of my clit and then I felt everything tighten up, and it felt like I was going to piss myself and I came, for real, I came so hard and long, it felt like my insides just drained out of my pussy. I realized that I'd never actually cum before.
We kept going. He made me cum twice more. I never felt so good all that pent up frustration was just gone.
We played a lot at night after that. He would instruct, I would get off. We got daring. He made me cum in dressing rooms, in my car stuck in traffic with a cop ten feet away, at my cousin's wedding, I was cumming all the time. I was like a new person. It was all so new and exciting.
I started to play back, sending him pics of my tits and giving him text blow jobs til he came. He sent me pics of his hard dick and videos of himself cumming. Then I sent him pics and videos of my pussy and of me cumming.
Work was getting tense. He's an older man, he's in his early fifties, I'm 22, he's married but I wanted him to fuck me. I wasn't in love but I was in lust I think. I looked at his dick pics and his cum videos all the time and fantasized about sucking him and him fucking me and cumming in me.
I made it clear if he wanted he could fuck me. He wasn't sure. I obviously turned him on. We were alone and he used his hand on me to make me cum, he was the first guy who ever made me cum it was glorious. I took his dick out, went to suck it, he said use your hand, I did. he wet it and I stroked it while he used his hand again. I came hard and when he was ready I opened my mouth and he put his dick in my mouth at the last second and I sucked him off at the end and I got a mouthful of cum.
He was upset he cheated. I understood and took a step back. A month later we were alone after hours and he asked me how it was going, I was frustrated and soon my pants were off and he was eating my pussy and fingering me, what the fuck it was amazing. So many orgasms.
Then he fucked me and we came together. After a bunch more fucks over the next few months he asked me what I thought. I was clear-I told him I just wanted him to fuck me or eat me, to make me cum but nothing more.
We both did feel guilty about his wife. She was nice and I was an asshole for fucking her husband, it would have killed her to find out. We fucked a few more times then I met a guy, went on a few dates and had sex and kept dating. At first it wasn't great but it got there then it was better. Actually being with the guy was so much better overall.
Me and my boss just naturally stopped everything when i got serious with the other guy. He missed me and felt loss but I think it was a relief for us both. I still have the pics and videos of him and check them out now and then and I still re-read some of our text threads to get myself off he was amazing. I hope he does the same.
And what he doesn't know was that he took my virginity with a hairbrush then took my actual virginity on the couch in his office. My boyfriend thinks he was my first because I didn't know what else to say but it was really my much older married boss. I think that'll be a secret forever.
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