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My Boss and Her Husband

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After reading everyone’s stories and confessions, I thought it was time to add mine.

I’m a 35-year old single woman living in London. For the last 10 years, I have worked for an advertising company, and for the last six of those, my boss has been a woman called Carol, who is 54 and married with grown up children. I’ve always enjoyed working for her and she’s more like a big sister than a boss, always supportive and interested in me a person, not just an employee.

When my most recent long-term relationship broke up last summer, she was great, checking up on me to make sure I was okay, taking me out for lunch to make sure I was eating okay and giving me time off to make new living arrangements. A few months after it happened, she realised I wasn’t going out much, and invited me to spend the weekend with her and her husband at their beach house on the south coast. I should mention that her husband, Greg, is also very successful in business and they have several homes around the world, and having seen photos of them, it’s clear that cost is not an issue to them.

I was initially reluctant to go, still feeling miserable about the break-up, but Carol wouldn’t take no for an answer. Greg is a big golfer and would normally spend both days of the weekend out on a course, so I could keep her company, she told me. Realising how kind she was being, I accepted, so on the Friday afternoon, we finished work and got the train down to the coast.

We had a great evening, Greg cooked some amazing Thai food for us, and we sat around drinking wine and talking until the early hours. I slept in one of their luxurious guest rooms (far nicer than any hotel room I had ever stayed in), and the following day, Carol and I spent the day shopping, doing lunch and drinking cocktails in a bar overlooking the sea.

It was a great day, and by the time we got back to the house, we were both quite tipsy. Greg was already home and had made a pasta dish for us, and whilst we had dinner, he reminded Carol that his golf buddies were coming over that night for their monthly Poker game. She told him that wouldn’t be an issue, and that she and I would go and watch TV upstairs, out of the way. We finished the meal, cleared up and then Carol fetched another bottle of wine from the kitchen before we went up.

She told me that we might as well treat it like an adult sleepover, and suggested we put on our PJs, did some face masks and watched a movie. I went off to my room to change into my silk shortie pyjamas, and when I got to her bedroom, she was already stretched out on the bed wearing a similar set. We set about pampering ourselves, drinking the wine as we did and giggling like schoolgirls over the rom-com we were watching. After that ended, she asked if I fancied watching another movie, as it was only 10pm, and I agreed. I wasn’t paying attention to what she selected, but after the first ten minutes, I guessed it was a porn film as the sex scenes were really graphic.

I watched intently as the characters fucked doggie-style, but then noticed that Carol was breathing heavily. I glanced over to make sure she was okay, and suddenly realised that she was masturbating, with one hand up her top and the other in her shorts. She saw me looking and smiled.

“Does this turn you on?” she queried.

“Ummm…. well….. I’m not sure,” I replied, not sure what to say.

“It’s okay if it does. All girls together here. When was the last time you had sex, Vicky? Must’ve been months ago now?”

I blushed. “Well, yes it is, but…. I can’t face the thought of meeting someone else right now. I think I’ve been put off men for life!’ I laughed. “Well, that’s a shame,” she whispered. “But, then, there’s still women….”

As she said that, she leaned over and kissed me. I was completely stunned, but whether it was the shock or the alcohol, I didn’t pull away. I had never so much as kissed another woman before, but this felt nice, and before I knew it, I was kissing her back.

We continued to make out like that for a while before she slid her hands up my top and began to play with my breasts. Her touch was incredible, firm but still gentle, and I moaned as fingertips began to trace my nipples.

“You like that, baby?” she questioned as she lightly pinched them.

“Yes, but Carol, we shouldn’t. What about Greg, what if he walked in now…..”

She laughed out loud. “Honey, if Greg walked in now, he would LOVE it! We often involve extra people in the bedroom. I thought you realised we were swingers? No? Yes, we are. In fact, the guys he’s playing cards with tonight? I have fucked all of them before, several at the same time. Greg’s always liked groups, and when he sees me with another woman, wow it turns him on! So don’t worry about him. Now, where were we……”

As I tried to rapidly process this news, Carol began to unbutton my top, revealing my larger-than-average tits. Without saying a word, she moved straight in, taking one nipple in her mouth as she used her hand to squeeze the other. Her tongue lapped and swirled at the sensitive tip and I could feel myself getting wetter with every stroke.

Silently, she removed my top and slid off my shorts, before undressing herself. For a woman of her age, she had an incredible body, much better than mine. Firm tits, I would guess around 36C, a flat stomach and a completely shaved pussy, compared with my clutch of dark curls. She got on top of me and began rubbing her body over mine whilst French kissing me. It was incredible, no guy had ever turned me on like this.

After a while, she leant her chest over me and asked me to suck her nipples, which I was only to happy to do. I imitated the action she had used on me, taking the large discs into my mouth and lightly grazing the teat with my teeth, and she murmured appreciatively. Again, without saying a word, she spun around so that we were in a 69 position and began to lap at my soaking pussy as she lowered her own onto my face. I breathed in her scent, so feminine and sexy, and used my hands to open her up and get access to her clitoris.

We pleasured each other orally for a while until we both came within a minute of each other, and collapsed into a cuddling position whilst we recovered. I asked if I should go back to the guest room, to which she said no, she wanted me to stay with her. The wine and orgasm had exhausted me, and I fell asleep curled up to her, suckling on her tits.

I couldn’t say how long I was asleep for, but I woke up still facing Carol’s amazing breasts. I felt disoriented, as her body appeared to be moving, then I suddenly realised that she was being fucked in a spoon position. I lifted my head to speak to her, but as I did, she immediately began kissing me and fondling my boobs. I really had no idea of what was going on, or who was in bed with us, but her touch felt as good as the first time, so I let her carry on.

The action stopped momentarily as she got onto all fours and crawled over me, briefly sucking and licking my nipples before diving into my pussy again. At that point, the guy – who I realised now was Greg – mounted her from behind and started to pound her, hard. People say there is nothing sexier than watching another couple have sex, and this is almost true – watching another couple have sex whilst the woman is going down on you is simply another level!

It was no surprise that I climaxed quickly, especially as Carol had been fucking me with two of her fingers whilst she lapped at my clit. I lay there for a minute, watching the action, until Greg suggested that I join in by giving his wife some oral attention. She spread her legs so I could slide underneath them, and I began to lick her out whilst her husband’s very wide cock slid in and out of her. I reached up to squeeze her tits as I did this, and she moaned loudly. I was started to build up the pace when Greg’s dick slipped out of her pussy. I thought this was just an accident, until he grabbed my hair and asked me to suck him.

He tasted of her juices, so I gladly licked and sucked his member like an ice lolly, before he pulled out and entered his wife again, thrusting even harder than before. This was too much for her and she came, loudly, collapsing onto me as her pussy contracted violently. Greg was still hard as he’d not climaxed, and he lay back on the bed with his erection pointing up to the ceiling. It was huge – maybe as much as nine inches – and he stroked it as he spoke to us.

“So, Vicky, I hear you’ve not had a guy for a while….wanna ride this sweetheart?”

I paused and looked at Carol, knowing I needed her approval.

“Go on,” she smiled. “Treat yourself. I’ll just have a minute to recover, and then I might join in as well.”

I crawled over to Greg and climbed onto him, lining my hole up with his giant cock. He reached to hold my hips as I gently sank down onto him, savouring each inch as it filled me up. I began to lift up and down slowly, adjusting to the sensation of his width stretching my unused pussy. It felt so good and I started to ride him faster as he squeezed my bouncing tits.

“Carol sweetie, I think Vicky’s titties need your attention. Come sit on my face will you?”

She did as he asked, climbing over his head so that he could lap her pussy as I rode his dick. She reached out for my boobs, rougher than earlier as she pumped at them and pinched my nipples, making them stick out more than they ever had before, then leaning over to nibble them. I did the same to her, and again, we both came within a minute of each other, both screaming as we did. Greg quickly followed, grunting and then filling me with hot, sticky cum, which started to leak out as I dismounted him and lay down between the two of them.

“Carol, are you going to clean Vicky up?” Greg asked, encouragingly.

Without saying anything, she got between my legs and starting to lick her husband’s juices from me. My clit was so sensitive after all of the orgasms I had already had, I didn’t think I could take any more, but almost as if he sensed I was going to pull away, Greg leant over and started to kiss me, hard, pushing his tongue into my mouth as his wife pushed hers into my snatch. His hand made its way to my tit, stroking my still erect nipple and tweaking it between his thumb and finger. To my absolute surprise, another orgasm took hold of me, the contractions pushing Greg’s cream into Carol’s eager mouth, which she swallowed up.

After kissing them both goodnight, I returned to my room, exhausted but exhilarated from the best sex I had ever had. I slept for hours, until later morning when Greg brought me in a cup of coffee and told me that Carol had already gone to her tennis lesson, at which point he laughed and said that basically meant she had gone to fuck her twenty-something tennis coach, and would be back for lunch.

I told him that I wanted to have a shower before I did anything else, and was taken aback when he asked if I would like him to join me. I knew that Carol wouldn’t mind, and that it would be a while before I would have sex again after this weekend, so accepted. We fooled around under the water, soaping each other up and kissing, until Greg offered to wash my hair for me. I didn’t know what he meant, but he pushed me to my knees and started to lather my hair with shampoo with one hand, whilst guiding his erection into my mouth with the other. I kissed and licked him, swirling my tongue over the bulbous head and sucking his balls into my mouth until he told me my hair was done, and lead me back to the guest room.

We were both still soaking wet from the shower, but he pushed me back on the bed, climbed on top of me and pushed himself deep into my pussy in one single thrust. He was passionate and horny and played with my tits as he fucked me. As I neared my climax, he grabbed my ankles and forced my legs over his shoulders, giving him even more depth and the perfect angle to hit my g-spot, making me cum hard, not once, but twice.

He allowed me a moment to recover, masturbating himself as he sucked my nipples, before asking me if I had ever had anal sex before. I blushed as I admitted that I hadn’t, to which he then asked me if he could be my first. I told him I wasn’t keen as I thought it would hurt, but he promised me he would be gentle and would stop if I didn’t like it, so I agreed. He went back to their room to get some lube, and then came back and got me to lie on my front with a pillow under my hip to lift my ass a little.

I expected him to start straight away, but he didn’t, instead kissing my neck, shoulders and back whilst touching my boobs, pussy and ass. Once I had relaxed, he started to rub lube over his dick, and some between my cheeks. Gently, he inserted a finger, stroking it in and out, before adding a second. It felt a little odd, but not too painful. After that, he climbed on top and pushed his cock against me, telling me to relax. As the head started to enter me, it did hurt and I started to tense up, but as he pushed further, I felt the pop that everyone describes and I slowly started to open up.

He took it really slow to start with, but as I got used to him, built up his speed, clearly enjoying it. After a few minutes, he pulled me up into a proper doggie position which gave him access to finger my pussy and clit, but he came before I did, filling me with more of him sticky liquid. He gently pulled out, thanking me for letting him be my first anal lover, then cuddling me whilst using his fingers to make me come a second time.

We rested for a while and then got dressed, and shortly after, Carol returned. She told me that she had indeed fucked her tennis toy boy, and asked me if Greg had been ‘looking after me.’ I told her about the shower and the anal experience, which she was delighted to hear about, and then we all went for lunch, before heading back to London.

I’ve not had sex with either of them since that weekend, but she and I still have a great working relationship. I’m still single, and she keeps asking me if I want her to set me up with one of Greg’s golf buddies, and I’m starting to think that I might just let her do that. Hopefully their wives will be as willing to share as she was……

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