Straight Female / 39
Sex With My Boss
I had a long-term boyfriend who I loved more than life; we started dating when I was 14, and it lasted until I was 20. He cheated, and I found out, which resulted in a horrible break-up. I was devastated, lonely and my self-confidence hit rock bottom. He was the only boy I’d had any sexual relationship with.
I’ve worked for a company since leaving college at 18. I loved my job, and the business owner, Phil is a great guy; he’s in her 50s, not good looking, and overweight, but he has taught me loads. I was upset following the breakup, and Phil was very supportive, even letting me have some early finishes when my emotions were terrible. It’s fair to say we become very close in the year after the breakup, almost like a second father.
Phil’s wife is terminally ill with cancer; she has diagnosed about five years ago and has had a terrible time spending months in hospital. Phil has been brilliant; he rarely complains at work, but I knew he sometimes felt dreadful.
I was working late one night and heard a noise in his office, so I went to check. Phil was in his office crying; I was shocked and felt so sorry for him, so I went to hug him. As he sobbed, he said that he missed just holding a woman. Anyway, we hugged for about 5 minutes, and then he asked very sheepishly if he could touch me. I didn’t know what to say, but, in a way, I did love him and was grateful for everything he had done for me. I have also really missed the physical relationship with my boyfriend and enjoyed just hugging a man again. I wasn’t turned on at first; however, Phil wears this expensive aftershave I’ve always liked, which smells sexy. I didn’t respond to his request, and I didn’t know what to say. Part of me wanted to please him, but another part of my brain was screaming “no”
As this maelstrom of emotions and thoughts whizzed through my head, Phil started to touch my breasts over my blouse. I initially tensed up, but I liked his large hands squeezing me, and I decided, in the end, to go with it. I’ve never thought of myself as a submissive, although I had the usual teenage dreams of being swept off my feet by a tall, dark, handsome prince and ravaged as a reward for saving my life. His fingers were shaking as he opened my blouse and put his hands into my bra. I adored having his large hands on my bare boob. He knew what he was doing too. He had my nipple between two fingers and was massaging the whole of my tit with his hand at the same time.
He started to kiss me, and I loved the smell and taste of cigar mixed with that sexy aftershave. I was getting turned on; next, he opened my blouse completely and pushed my bra up, releasing my 34C boobs. His lips left mine and sucked on each of my nipples in turn. I loved just surrendering to my boss, knowing I was also bringing him comfort and happiness in my submission. Phil was worshipping my breasts and bringing me such pleasure; he also complimented my tits, stating how beautiful my breasts were, the best he’d ever seen or felt.
His lips returned to mine as I then felt his hand go down to my pantyhose knee and begin its journey up my skirt. This was to going too far; no man except my ex-boyfriend had ever touched me here. Phil’s hand was now at the top of my pantyhose and working down them towards my knickers. I wanted to shout stop but again just went with it. His hand reached my crotch and began to rub my cotton-covered pussy. I could hear the squelching sound my pussy was making; I was loving the feeling of having my secret place rubbed; it felt so very naughty. It didn’t take long before his hand was in my knickers, fingers separating my wet pussy lips. I shuddered when he touched my little love bud. Finger now at my entrance, his fingers were so big, so much bigger than my ex-boyfriend’s. A finger in me and then two.
I didn’t stop him as he pulled my underwear off and laid me on his desk. I gasped when I saw the size of his penis. It wasn’t long like I’d seen in porn movies; however, it was very thick, almost as wide as my wrist. He entered me slowly, which I was thankful for. I’ve never been so stretched out and filled before. I had an orgasm as soon as he was entirely in me. He fucked me for about 10 minutes which was brilliant. I liked being used by my boss, and I liked the feel of his cock in me; I liked the feeling of giving this wonderful man pleasure. Eventually, he sped up, his thrusts becoming urgent. I had never felt so taken in my life. He came long and hard; I could feel his massive cock pulsating in me. I had another huge orgasm as I felt his cum exploding inside my private place.
A couple of days later, my ex-boyfriend turns up, says he still loved me and had regretted what he had done. I initially told him to fuck off, but he then gets down on one knee and asks me to marry him; I said yes. That was all a few years ago; however, although engaged, I’m still having an affair with Phil. I’ve even fucked them both on the same day. My fiancé has no idea his penis must have had another man’s cum on it a couple of times, and once, he even went down on me after Phil had fucked me. The idiot thought I was so wet because of him.
I’ve worked for a company since leaving college at 18. I loved my job, and the business owner, Phil is a great guy; he’s in her 50s, not good looking, and overweight, but he has taught me loads. I was upset following the breakup, and Phil was very supportive, even letting me have some early finishes when my emotions were terrible. It’s fair to say we become very close in the year after the breakup, almost like a second father.
Phil’s wife is terminally ill with cancer; she has diagnosed about five years ago and has had a terrible time spending months in hospital. Phil has been brilliant; he rarely complains at work, but I knew he sometimes felt dreadful.
I was working late one night and heard a noise in his office, so I went to check. Phil was in his office crying; I was shocked and felt so sorry for him, so I went to hug him. As he sobbed, he said that he missed just holding a woman. Anyway, we hugged for about 5 minutes, and then he asked very sheepishly if he could touch me. I didn’t know what to say, but, in a way, I did love him and was grateful for everything he had done for me. I have also really missed the physical relationship with my boyfriend and enjoyed just hugging a man again. I wasn’t turned on at first; however, Phil wears this expensive aftershave I’ve always liked, which smells sexy. I didn’t respond to his request, and I didn’t know what to say. Part of me wanted to please him, but another part of my brain was screaming “no”
As this maelstrom of emotions and thoughts whizzed through my head, Phil started to touch my breasts over my blouse. I initially tensed up, but I liked his large hands squeezing me, and I decided, in the end, to go with it. I’ve never thought of myself as a submissive, although I had the usual teenage dreams of being swept off my feet by a tall, dark, handsome prince and ravaged as a reward for saving my life. His fingers were shaking as he opened my blouse and put his hands into my bra. I adored having his large hands on my bare boob. He knew what he was doing too. He had my nipple between two fingers and was massaging the whole of my tit with his hand at the same time.
He started to kiss me, and I loved the smell and taste of cigar mixed with that sexy aftershave. I was getting turned on; next, he opened my blouse completely and pushed my bra up, releasing my 34C boobs. His lips left mine and sucked on each of my nipples in turn. I loved just surrendering to my boss, knowing I was also bringing him comfort and happiness in my submission. Phil was worshipping my breasts and bringing me such pleasure; he also complimented my tits, stating how beautiful my breasts were, the best he’d ever seen or felt.
His lips returned to mine as I then felt his hand go down to my pantyhose knee and begin its journey up my skirt. This was to going too far; no man except my ex-boyfriend had ever touched me here. Phil’s hand was now at the top of my pantyhose and working down them towards my knickers. I wanted to shout stop but again just went with it. His hand reached my crotch and began to rub my cotton-covered pussy. I could hear the squelching sound my pussy was making; I was loving the feeling of having my secret place rubbed; it felt so very naughty. It didn’t take long before his hand was in my knickers, fingers separating my wet pussy lips. I shuddered when he touched my little love bud. Finger now at my entrance, his fingers were so big, so much bigger than my ex-boyfriend’s. A finger in me and then two.
I didn’t stop him as he pulled my underwear off and laid me on his desk. I gasped when I saw the size of his penis. It wasn’t long like I’d seen in porn movies; however, it was very thick, almost as wide as my wrist. He entered me slowly, which I was thankful for. I’ve never been so stretched out and filled before. I had an orgasm as soon as he was entirely in me. He fucked me for about 10 minutes which was brilliant. I liked being used by my boss, and I liked the feel of his cock in me; I liked the feeling of giving this wonderful man pleasure. Eventually, he sped up, his thrusts becoming urgent. I had never felt so taken in my life. He came long and hard; I could feel his massive cock pulsating in me. I had another huge orgasm as I felt his cum exploding inside my private place.
A couple of days later, my ex-boyfriend turns up, says he still loved me and had regretted what he had done. I initially told him to fuck off, but he then gets down on one knee and asks me to marry him; I said yes. That was all a few years ago; however, although engaged, I’m still having an affair with Phil. I’ve even fucked them both on the same day. My fiancé has no idea his penis must have had another man’s cum on it a couple of times, and once, he even went down on me after Phil had fucked me. The idiot thought I was so wet because of him.
- That's Juicy! 49
- Remove It! 0
# 51392 - by
Rothco / May 14, 2021
