Maid for pleasure (2)

Wow. Was that a huge hurdle I’d just jumped? A Beechers Brook? Or was it a tiny tiny step in the right direction? (Here in case you missed it: https://medium.com/@TracyTrouble/maid-for-pleasure-9cc49e1e2078 )

I wasn’t joking when I told you I’d vowed to rip the next cock I held free of its owner so I guess I can say what I had done was definitely a Beechers Brook moment.

I sank back on the sofa and felt as exhausted as if I’d ridden the Grand National. Not that I ever would, I don’t have that level of courage. I reached for my glass and took a large gulp. My Spritzer! Wine and piss mixed. I could definitely get hooked on the combination and it occurred to me what fun it could be to serve it at a party without mentioning the contents to anyone!

“Well?” Carol’s one word question didn’t need expanding.

“Yes. Very.” I looked at Charles-Rose, “Thank you, Rose. Your impeccable manners and devotion to duty should earn you a treat. I’ll have a word with your mistress.” I kept the thanks light. I’d thank him properly later. His attitude had been perfect. I doubt it would-could-have happened otherwise.

“Carol, don’t you think Rose deserves a treat?” This role-playing was totally alien to me. I had no idea if I was doing it right, but what the hell, it was fun.

“I suppose so, but I don’t like spoiling her. What had you in mind?”

“Given she’s already cum twice perhaps we should put on a show for her.” I had an ulterior motive for the suggestion. My libido was kicking up a fuss. My body fast recovering from the exhaustion of recent happenings and wanting action. Proper sexual action.

“Well, given you are also ‘supposed’ to be a maid, I might let you lick me.” I went to stand up to go over to her. “No! On all fours. I want a dog. A puppy to lick me.” Wow, this was getting kinky. Did I mind? Of course not!

I dropped onto my hands and knees and padded over to her. “Good girl. Sit.” I sat.

Carol edged to the front of her chair and opened her legs. “Remove my knickers. Remember you’re a puppy.”

What did that mean? Should I wag my bum? Bark? I went to pull her knicks down and realised. A dog didn’t have hands. She wanted me to take her knickers off with my teeth? Really? Not being one not to accept a challenge I padded forward and pushed my head up her skirt, managed to get hold of the gusset of her panties in my teeth and tugged. Hardly any movement. Carol wasn’t helping at all and with my mouth full and my head up her skirt I had no idea how I should proceed. I tugged some more. Shook my head like a terrier with a rat. It was actually fun but hardly sexy. Eventually, Carol raised her bum and I managed to pull the recalcitrant garment down her legs. “Good puppy. Now you may lick me.”

I needed no second invitation. I had by now decided I had indeed fallen down a rabbit hole. If asked for a name as a maid I would ask for Alice.

She opened her legs wider and my tongue began working on her pussy. I wanted to use my fingers too but remembered I was a dog. My tongue was doing a good job judging by the juice flowing from Carol. “I can’t see your tail wagging.”

Tail? Best I could do was waggle my bum. Which I did. “Good girl. Keep going. A puppy’s tongue there is divine.”

It was ridiculous that this bizarre role play could be sexy but it was. I was leaking as I continued with my head up Carol’s skirt licking her. That’s when I felt a hand on my bum. A finger gently running ever so slowly down my cheek crack towards my holes. God yes! Carol was going to finger me. I needed it. I was in desperate need. Then realisation! It couldn’t be Carol. She hadn’t moved from her slouched position in the armchair. God! It was Charles! A MAN! Touching me. About to put his finger in me! I froze. The finger stopped moving. But then. What the hell? I told myself to pretend it was Carol. I’d lie to that part of my brain that kept telling me to stay away from any Homosapien with an appendage in their groin. Unfortunately, that part of my brain could see through the deception. No way! it screamed. I managed to mutter some words from deep up Carol’s skirt. “Not in me!” I forced the resumption of my licking. The finger resumed traveling down my crack. It arrived at my bum hole. I trembled, still with my tongue lapping at Carol's clit. I needed to divert my mind Away from that finger. I thought I’d freak out, but I didn’t. I was on the edge though. I tried to focus on Carol's pussy, but the proximity of that digit to my anus was causing me severe concern. I intensified my licking. Charles couldn’t see that, but could no doubt judge I had by the rate my head was raising and lowering Carol’s skirt and by the increasing noise emanating from his wife. His finger started circling my anus. My friend could see what her husband was doing. I think it tipped her. She erupted. Sixty years old and she yelled like a teenager, her hips bucked, viciously crashing her cunt into my face. I couldn’t worry about it. I was coming myself, which was a shock considering that finger. Carol continued bucking like a bronco in a wild west show. On and on. I tried lapping her juices, but her body was contorting too severely. Charles's digit was no longer touching me. He’d lost contact as I had with Carol. Then eventually her eruption subsided and mine started. Whether because of or in spite of Charlie’s finger I couldn’t decide But the feeling began slowly, the intensity built and then boiled. My contortions were not as physical as Carol's but I was as vocal. I collapsed on the floor. Sitting on a very damp carpet. Rose would be busy.

Oh boy.

“I hope you didn’t mind,” said Charles.

I managed a smile. I voiced my thoughts. I had to be honest. “I came, didn’t I? I’m just not sure whether that aided or hindered.”

“I understand, but being a gentleman I thought I should ask,” he replied.

“A gentleman? I thought you were a maid? If I’d known you were a man I’d have castrated you on the spot.”

He laughed. “In that case, madam, may I serve you a drink?”

“You may.”

The exchange was light. I truly didn’t know how I felt about his contact.

An interlude was needed. Time to reflect. I’d let a man touch me sexually and hadn’t freaked out. Admittedly he was one I knew well, almost a father figure, but he was male. Even if dressed as a female. Was that how I’d coped? So far removed from the macho stereotype that my Hex of a husband had morphed into. Perhaps my brain couldn’t make the connection. After all, it wasn’t the process of another human putting part of themselves in me that was abhorrent. I readily accepted anything from my girlfriends. So was that a way forward? Have male partners dressed as women? Too early to say. I knew deep down I’d need time to assimilate what had transpired that night. To make sure I fully understood what I was permitting. But then was not the time for introspective thinking.

We’d all been satisfied. We’d all cum. And I’d crossed so much barren ground. I was elated.

As on previous visits, these interludes after a bout of sex started with silent reflection. (Ha! I make it sound like a religious retreat! Wouldn’t that be something popular? I suspect church going might increase if every service ended with an orgy!). What Carol and Charlie were reflecting on I didn’t know. Were they wondering where this friend was taking them? Was I taking them? Or were they taking me? How much of what we were doing was new to them? Initially, I’d thought most of it, but now I wasn’t sure. The revelation that they had participated in swapping partners was a surprise, but I had to keep telling myself that my revelations must have been equally as surprising o them.

It didn’t matter anyway. The journey was exciting and fulfilling.

I sat there musing, sipping my spritzer. The other two weren’t drinking pee, either neat or mixed. That was definitely something that they didn’t appear to enjoy.

“Hun,” Carol eventually broke the companionable silence, “I don’t want to press you, but I’ve got an urgent need. I desperately want Charlie to screw me. We can go upstairs if you like but I wondered if you’d want to watch? See if we can’t get rid of another demon.”

Carol clearly felt watching a cock in action was a problem for me. After what we’d done I felt relaxed about it. “Do it here, Carol. I’m happy to watch” I said lightly.

Charlie slipped out of his maid's outfit apart from his stockings. I felt a stirring as I watched him give his cock a couple of tugs. I was going to have to revise my preconceived notions of older men losing their virility. Three times in a couple of hours. Mind you from what Twitter followers have told me that’s not exceptional. That’s as maybe, but it is in my sphere of personal experience.

Carol stood up, unzipped her dress, and lost her bra, her knickers hadn’t been replaced. They settled onto the sofa and began kissing and some mutual fondling.

It was like watching a porn movie. My hand went between my legs. Yes, it was like watching a porn movie, I was dampening. Not that my cunt was an arid desert. I’d leaked most of the evening, but the rest we’d had, had stopped the flow for a while.

I was jealous of Charles, he had his hands roaming all over Carol. I wanted to do that. I admired her body. So slim for her age. Not muscled, but no fat anywhere. Her tits were more than adequate. I know you all seem to rave about mine but being the size they are, when they droop… no I don’t want to go there. There was no sign of drooping with Carol’s.

Things between the two were urgent and Charlie was already in her. The act left me decidedly underwhelmed. I was still watching. I was still admiring Carol's body. But I could take or leave Charlie’s penetration of her. God, I’m a mixed-up specimen. Was that because I was jealous? Wanted my fingers, my tongue, to be doing the stimulating? Or was it residual hatred of cock violating vagina? Fifty, fifty I guessed.

It didn’t take long. They both had urgent needs. I mused on how much cum Charlie had produced this time. As if reading my thoughts Carol said, “Fancy licking me out Hun?”

I was off my chair in an instant. Almost between Carol’s legs before Charles had fully withdrawn. I needed to taste her. To savour her juices mixed with Charlie’s cum. A cocktail I’d never experienced. My tongue worked overtime. My lips sealed the entrance to her love tunnel and I sucked for all I was worth. The overriding taste was of her juice. It was hardly surprising Charlie’s contribution was minimal. But I was content. I now knew for certain that feeling, touching, tasting a man’s semen deposited on my body, on his cock, or deep in a woman’s vagina was not going to freak me out.

We all collapsed again and this time I was offered, and gladly accepted a glass of wine.

It took a while for it to sink in but I realised that I hadn’t had the pleasure of anyone playing with me. Apart from Charlie’s recalcitrant finger, no one had put anything in or near my cunt. Yet I felt sated. Content.

Then the fact of my virginity that evening dawned on Carol. “Oh Hunny, I’ve just realised you haven’t had anything. Can’t let that happen. Even if you are the hired help!”

I didn’t reply, just sat there and watched my best friend come over, kneel between my legs and give me the most gratifying orgasm with her mouth.

Another high to come down from.

We sat for a while and then as I’d hardly drunk any alcohol I decided to go home. Staying the night could have proved exciting, but I wanted the comfort of my own bed and quietness to reflect on what had happened.

What had happened? There were two very different parts to the evening. The sexual perversion part. The dressing up, being a cum dump (perhaps a bit OTT) the lesbian sex part. And there was the ‘journey progress’ part.

That was what I needed to think about. I could and would enjoy the perversion part in my mind and with my fingers often, but I needed to be clear in my mind where I was going. Where I wanted to go.

I’d touched a man’s cock tonight. Something two years ago I’d sworn I’d never do again. Even a few months ago I’d regarded the chances of it happening willingly to be remote. But I’d done it and the sky hadn’t fallen in. That was the good news. Was there bad? Well, it had taken a superhuman effort on my part to force myself to do it but then I suppose the first time doing anything is the hardest. What I needed to be honest with myself about was how much satisfaction I’d got from it. I don’t mean satisfaction from overcoming my prejudice. That was high. Sky high. I was proud of myself. I mean sexual satisfaction.

My previous most recent experiences of handling a cock, being gratified by a cock, were before I’d experienced the touch of a woman. (I am talking about a time when it was still pleasurable and not an enforced requirement of my marital state.)

Was it fair to compare the two? Were my memories of that dark past still clouding my mind? Holding back my willingness to fully enjoy what a cock can do?

I hadn’t fully experienced one anyway. I’d only wanked it. Not sucked it. Not had it fuck me. Either in my cunt or bum. Was I comparing like with like? Jane and Mary had been no holds barred encounters. I’d allowed them to do what they wanted. They’d allowed me to do what I wanted.

As my mind wandered it became obvious what I was saying to myself. At that point, my sexual encounters with my female friends had given me so much more satisfaction. But, and it was a huge gargantuan but, I realised I wasn’t being fair. It was almost like going back to those teenage days and the first fumbling gropes from a boy. How many of us (I’m talking girls here!) got anything sexual out of it? If we’d been told, that’s it, you won’t get more turned on than that, then I wonder how many would have bothered doing it again. I’m not sure I would.

So to judge hetro versus lesbian off the back of that one night would be wrong. And I won’t. I can see too much possible fun from expanding my field of play!

https://medium.com/@TracyTrouble/membership