Lessons Whilst Riding Ch. 03

The next time I encountered Mrs X was at their house on the eve of the Millenium. Rachel and I were now married, both working in London, me in investment banking and Rachel for a startup tech business when that was still an alien phrase to most people.

Mr & Mrs X had invited us all to a 'Millenium ball' their local hunt was holding which provided the perfect opportunity for a catch up with the old school gang and Chloe. Thankfully Rachel and I had not got caught up in all the worry about systems failing to work after midnight on the 31st of December 1999, so we were able to head off to Tiny's parent's house just after lunch making it there by mid-afternoon.

Mr & Mrs X greeted us warmly before showing us to the room we would be staying in, something far grander than the digs I had that glorious summer, the centrepiece being a four-poster bed. Mrs X winked conspiratorially as they showed us the room, stressing to Rachel that she'd left her a few ladies things in the drawer if she needed them.

Mrs X gave us both a hug suggesting we meet downstairs in a couple of hours for drinks before heading off to the venue, giving us time to get in our finery. Apparently, we were the only couple from the school gang staying in their house, the others staying at Tiny's instead. There'd obviously been some planning behind the scenes, a fact that left me intrigued and a little hopeful.

Rachel and I had obviously discussed our last liaison with Mrs X on the drive up, all of it very fondly remembered, and Rachel was as hopeful as I that something would happen. She said she still got wet at the thought of when Mrs X had first tongued her pussy and when she had eaten a pussy for the first time, one that also happened to be dripping with my cum. We'd never pursued any threesomes since and, honestly, were unlikely to unless it was with Mrs X. We didn't want to get involved in any 'scenes' and with Mrs X it felt safe and unlikely to become anything beyond a bit of fun.

Once we were alone in the room Rachel sprung on me like a cat, pushing me on to the four-poster bed where we were soon naked and exploring each other's bodies. Rachel was in the process of giving me a lovely blowjob when she hopped off the bed.

"I'm sorry darling but I'm intrigued to find out what 'ladies things' Mrs X has left us. There was something about the way she said it." Rachel started sorting through the drawer, declaring after a while, "she's been very thoughtful. We've got a padel and a riding crop, for my arse or hers I guess, silk ropes, lube, blindfolds, a vibrator, some uniforms, a butt plug and a strap on." Rachel brandished each item as she called them out.

"You can forget any ideas you might have about fucking my arse darling," I told her.

"Spoil sport. I do like the idea of being tied to a four poster and fucked. Would you oblige Tom?"

"Of course I will."

Rachel was soon spread out on the bed, face down and with a pillow shoved under her stomach so her bum and pussy were available to me. I love nothing more than eating Rachel out from behind as tonguing both her holes seems to make her even wetter than usual. I think the act of being restrained turns her on and it definitely excites me. I moved from eating Rachel to pushing my cock in to her mouth whilst I caressed her bum, slapping it occasionally with my palm. I thought how nice it would be if Mrs X walked through the door, a thought that made me throb inside Rachel's throat, but that didn't seem to be on the cards as I started fucking Rachel's pussy hard, driving her towards a climax with my own seeming to be a long way away.

"Oh my God, it must be the angle Tom, but your cock is driving me crazy." Rachel moaned as I fucked her.

She raised her bum a little and I felt her fingers reach underneath to diddle her clit as she started thrashing about, clearly racing towards a climatic finish.

When that climax arrived, it was big, but I didn't cum at the same time for once. I thought I'd be cheeky, literally, and moved to lick Rachel's arsehole in readiness to fuck it but I was met with a hand resisting my endeavours.

"I'm sorry darling, I'm just too sensitive at the moment. I'll pay you back later, I promise, but we should be getting ready now."

Trying to get dressed in black tie is not easy with blue balls and a semi hard prick but that's where I found myself, constantly being presented with temptation as Rachel dressed up in an amazing lingerie set and, just before the ball gown went on, she cruelly asked me to push the butt plug in to her.

With only 10 minutes to go before we were due downstairs this was the ultimate tease, a situation that made me wonder if they'd deliberately conspired to make me as frustrated and backed up as possible. Whatever the truth was Rachel, at the least, was going to be on the receiving end of a spanking and a good hard ass fucking later.

I'll skip most of the details of drinks downstairs and then the meal, bringing us to the end of the evening where I was slow dancing with Rachel. I had remained sober as, by the time it became apparent that the taxi was letting us down, I had only managed a sip of beer where the ladies and Mr X had made a good dint into some champers. Again, more frustrations that needed to be vented later.

"What are you thinking Tom? You feel hard." Rachel half whispered as we danced.

"I'm thinking how I'm going to fuck you into the new millennium later, whilst I spank your delicious behind with the paddle Mrs X left us."

"That's nice darling. Any thoughts on how you might make Mrs X lick your cum out of there too?"

"Stop it, Rachel. I doubt that will happen, she seems to be having quite the talking to with Mr X."

On the way home Mrs X and Rachel sat in the back and appeared to be having a giggly girlie chat, most of which I couldn't make out as Mr X was talking loudly at me, slurring away as he related some story to me, much of it wafting over me as it was incoherent bollocks.

"You'll have to have a snifter when we get home Tom what with having to drive. I've got this very rare malt I think the turn of the millennium warrants." That piqued my interest slightly, but I'd still rather whisk Rachel to bed.

"I think you've had quite enough to drink darling," was Mrs X's interjection.

"Balderdash. I've got the constitution of a bull." Was his reply.

The mood was frosty when we got back with Mr X dragging me in to his study for a drink whilst Mrs X baulked at him that he could sleep in his own room if he was going to drink even more. She later handed me a cup of cocoa as she briefly entered the study to say Rachel and her were off to sleep. The scotch was delicious, as was the cocoa, but Mr X had definitely reached his limit as I soon found myself supporting him to his bedroom.

"Bloody bitch has shut her door, Tom. That's our rule, bedroom door open means I'm allowed in, if it's shut, I'm confined to my barracks."

He shook my hand as I delivered him to his door. I watched as he rolled on to his bed fully clothed and almost immediately started snoring. I was quite forlorn when I walked towards our room as I doubted Rachel would have stayed awake for another hour or so which meant I'd missed my opportunity for fun.

This was confirmed as I entered the room which was pitch black. I quickly undressed, cleaned my teeth in the en-suite and moved towards the bed.

The giggling happened as I tried to enter my side of the bed to find Mrs X, naked, I realised as my eyes had adjusted to the light, with Rachel fingering her gently.

"Happy new year darling," they said, almost in unison.

Suddenly I felt great again, my fugue gone, and a painfully hard erection arriving instantly.

"I see you approve," Mrs X sniggered, pointing to my hard cock.

I climbed on to the bed and pushed myself between Rachel and Mrs X, pulling them in for a hug and a kiss. Both of them then took in turns to either kiss me or suck my cock, a very pleasant turn of events when, moments earlier, I had been looking at a lonely night.

Mrs X was getting my full attention as her attempts to deepthroat me were causing her to make a choking type noise that was mildly concerning but equally exciting so I wasn't fully aware of Rachel's actions until she sat astride my face, pushing her pussy on to my mouth. I didn't really notice what was happening until she moved back, pushing her pussy towards Mrs X who then presented my cock for Rachel to impale herself on to.

"How does it feel to be tied to a bed with two very horny women looking to see the new year in properly, loaded up with a dose of Viagra?"

I pulled my arms as Rachel said this, realising her pussy had distracted me, and then I tried my legs to find my ankles were tethered to the bottom posts as well.

"Pretty good actually darling. I've not taken Viagra though."

"The hot chocolate I gave you was laced with it Tom. Sorry. Hubby needs it so I borrowed one of his."

I remember being painfully hard, the veins in my cock bulging as if I was wearing a cock ring. Rachel was clearing enjoying my hardened state as she bounced up and down on it like she was riding a horse. Because I was so engorged I had the sensation that Rachel's pussy was so much tighter than usual which enhanced my experience. The next enhancement came when I felt Mrs X suck my balls in to her mouth where she sucked, rolled and gently pulled them, driving me ever closer to a climax.

Mrs X dashed off the bed for a moment returning after a minute when I saw she pulled Rachel's buttocks apart and, I guess, started rimming her anus as Rachel declared her approval with an "Oh yes, you dirty bitch." After a while of this Mrs X moved up so she was playing with Rachel's tits from behind, my cock still rooted inside her, pulling and twisting her proud nipples.

"Are you ready for your treat Rachel?" Mrs X asked.

There was only a groan of "Oh god, go slowly," words I understood the significance of as I felt the hard penis of the strap on being pushed up into Rachel's arse, rubbing alongside my own cock through the thin membrane between her holes, causing Rachel's cunt to feel very tight as she remained still whilst Mrs X pushed in.

Once Mrs X had pushed the plastic cock all the way in, she smacked Rachel's ass and told her to, "ride us, you chose the pace."

I can tell when Rachel is sexually very happy, and this was no exception. Her face was a mixture of concentration, as she pushed back and forth on to our cocks, and pleasure, as the sensations the double penetration created overwhelmed her.

I couldn't really see anything but the sensations moving through my prick were amazing where I'd got a tight wet pussy clamped around me and a rubber cock rubbing against the underside, a feeling that was pronounced when Mrs X started thrusting to meet Rachel's own movements.

It didn't take much more of this to make both Rachel and I cum explosively with me sending rockets of spunk inside her and her squirting her own cum out and down between our legs. I felt Mrs X withdraw from Rachel, I saw her remove the strap on after which she climbed on to my face, clearly seeking a climax from my tongue. She tasted divine as she ground herself on to my mouth and tongue.

Despite recently cumming I remained hard, and Mrs X was reaching back to wank me whilst I brought her off with my tongue. I could tell Mrs X was very excited as her pussy was extremely wet with her juices dribbling all over my face. Rachel appeared to have revived as she began to undo the knots around my wrists and then my ankles.

"I hope you enjoyed your treat darling?" she asked as she started to suck my cock once again.

"I did but I still feel frustrated and little Tom here doesn't want to stop yet."

"We thought you might feel that way which is why we'd decided to grant you a millennium wish earlier. You name it, we'll do it. It's not long since I removed the butt plug so you can take my ass if you'd like."

"And I'm happy for you both to fuck me if that's what you fancy." Added Mrs X.

"What would you like Tom darling?" asked Rachel.

I'd been put on the spot and whilst my cock didn't really care I thought this benefitted a moments reflection before diving in, so to speak. Having just cum I got the sense I was going to stay as hard as granite for a while so I could be ambitious, I mused. No limits on which hole. Two women together, possibly a treat never to be repeated.

Rachel was trying to help when she suggested, "How about one of your stories Tim, you've got 2 women in bed with you on a four poster. Perhaps you are the lord of the manor, taking the new maids through their paces?"

Mrs X added, "Or you are using your mother-in-law to show your wife, her daughter, what a good lady of the manor should do in the bedroom. Suggesting if she doesn't start producing children, you'll hand her back, demanding an annulment."

An idea formed in my head, "I rather like the idea of exacting punishment on a pair of maids, who happen to be mother and daughter, having caught them lacing my evening cocoa with Viagra. The punishment must fit the crime and, as may father, the late lord, advised, never cum in a servant's pussy as bastard heirs create all sorts of problems. So, I'm going to tan your hides then I'm going to fuck you both until my cock gives up by which time your punishment will be served. I will be cumming only in your arses though. Understood?"

"Yes, my lord," they both said in unison.

"Very good, now, you need to properly attired, so I expect you in these maids' outfits by the time I return. You can decide who gets spanked first but, whoever it is, needs to on the rug by the fire her on all fours and pushing their arses up and open when I return. Is that understood?"

"Yes, my lord," they both replied again.

"Excellent, I am going to have a quick wash, so I expect everything in order when I return in 5 minutes."

My heart was beating fast as I retired to the bathroom where I took a very quick shower. I was grateful for the clarity of thought a lack of alcohol was giving me and slightly concerned how long it was going to take for my prick to recover from the drugs they'd filled me with. I'm not a pill popper and I am risk averse so I was a bit pissed off that the girls had done this to me but I took a moment to reflect, telling myself I hadn't keeled over yet so I was likely to be fine and I should enjoy working with a cock that was harder than I can ever remember. Despite cumming minutes ago, it was bouncing around, nearly upright like it used to when I was a horny teenager.

As I entered the room my heart very nearly gave way as I first saw Mrs X on all fours facing away from me, so I had a clear view of her bulging pussy and her tight arsehole peaking out from between her deliciously athletic buttocks. She had decided to adopt a position where she had both hands pulling herself open with her chest supporting her front rather than her hands as I'd envisaged when I'd requested 'on all fours'. I thoroughly approved.

Stood next to Mrs X was my beautiful wife, maid Rachel, who was holding out her hands with the paddle and a riding crop resting over them. She curtsied as I approached her, "here you go sir," she said as she offered them to me.

"Thank you, maid Rachel, but I'd like you to administer the punishment. I'm going to pull up a chair and watch. I will get involved if I think you are being gentle with your mother, understood?"

"Yes sir," replied Rachel.

"Very good. I wish to hear 'thank you sir' after each strike from Maid Rachel and I want to see colour on the cheeks. Understood?"

"Yes sir," they both replied. There was a sense of trepidation in both their voices which reminded me that this was supposed to bring pleasure but, I reminded myself, they had been frustrating me all evening and they had drugged me, so a punishment of some form was fitting.

"Excellent, 10 strikes with the riding crop then 10 with the paddle first please maid. You may begin when I'm sat down."

I moved an armchair, so it was closer to the action and sat down, naked, taking my cock in my hand as I prepared to watch this wonderful scene develop around me.

"Please begin."

As the words left my mouth Rachel swung the riding crop across Mrs X's buttocks. The sound it made was a bit light for my liking.

Before Mrs X had finished her thank you, I barked, "Too soft, add 5 strikes."

"Yes sir," Rachel replied.

The next strike made a loud thwack that made Mrs X falter as she said thank you. I didn't say anything, but I thought Rachel might want to tone it down as she was going to be on the receiving end next.

I watched each strike with great intent, a lovely maid in a revealing outfit with breasts spilling out and a naked pussy peaking out from between her buttocks, gently whipping her mother, whose buttocks rippled and coloured gently with each strike. I knew from my forays with Mrs X that she loved a spanking, memories of her clamping around my cock as I slapped her arse with my hand or her riding crop as I fucked her from behind stirring my loins.

By the time Rachel had finished her last strike Mrs X's arse was very red and sported two angry welts where Rachel had gone too hard. I beckoned Mrs X to approach me as she stood up as I wanted to inspect her arse.

"Does it hurt?" I asked as I stroked her buttocks.

"Yes, my lord," she replied which became a screech as I spanked her with my palm as a cheeky test. "Thank you, sir."

"Very good. Be a good maid and suck my cock whilst your daughter readies herself."

As Mrs X took my cock in her mouth, with great affection I noted, I instructed Rachel.

"Before we begin maid Rachel, I would be grateful if you would insert the butt plug back in to your delicious arse. I fully intend to bugger you once your spanks are finished. Is that understood?"

"Perfectly clear sir." As Rachel trotted off to prepare her arse I pushed Mrs X's head down on to my cock, aiming to fuck her throat whilst we waited for Rachel to return. I could feel my cock nudge into her throat which made Mrs X wretch slightly.

"Try again sir, I'll try to relax my throat."

"That's the spirit." This time, when I pushed, it felt like Mrs X was forcing herself down on my cock and I was delighted when I felt myself push in to her throat. We only managed 5 or 6 thrusts before Rachel was finished arranging herself on the rug in front of me.

"Thank you, maid. I think your daughter is ready now. As I said before, no going easy otherwise I'll have to revisit your own punishment. And maid Rachel, remember your manners. Understood?"

"Yes sir," they both replied.

Mrs X clearly wanted to thank Rachel as her first two strikes were sharp and strong. Rachel showed her strength of character in remembering her manners and they soon got into a rhythm, moving through the punishment easily. For my part I remained very turned on, my cock still wet with Mrs X's thick spittle and that glorious view where I noticed Mrs X was dripping juices down her stocking clad legs and Rachel's own pussy had flared open, something it did when she was very excited. As Mrs X administered the last strike with the paddle, I told her to re-assume her position next to Rachel on the pretext of wishing to compare their work but really it was so I could enjoy the view.

"Well done maids. I am happy you have each followed my instructions and been fair in your work. Now, I'd like you to remove the butt plug from your daughter's arse and then play with her pussy as I fuck her arse. Is that clear?"

"But she's my daughter sir?"

"You really should have considered that as you conspired to drug me. Now comply with my instruction or we can discuss your dismissal."

"Yes sir. Sorry sir."

I watched Mrs X pull the butt plug out of Rachel's arse as I slathered some of the lube from our drawer of treats up and down my painfully hard cock. I teased Rachel's bum hole and pussy with the head of my cock as Mrs X reached under to start fingering Rachel. As my cock breached the first inch or so of her arse, I paused allowing her a moment to get used to me and so I could take in the tight sensation which, once again, was enhanced as I felt Mrs X's fingers push into Rachel through the wall of her arse.

Holding the base of my cock to make it rock hard I thrust myself gradually in until I my balls pressed up against Mrs X's hand. I then started to move in and out, gradually building my rhythm until I was pounding Rachel's arse and Mrs X was matching my cadence with her hand, a combined assault which soon had Rachel cumming and squirting almost every ten pumps. I started to feel my own orgasm build after Rachel had come for the fifth time, a tightness starting in my balls that felt like it would lead to a sizeable cum for me.

I pulled back on Rachel's hair and bent down to kiss her as I felt my orgasm consume me. I am not sure I have cum like it since, but I swear it felt like my balls pulsed as I came, painfully, sending what felt like a huge volume of cum inside her bowels. That warm injection seemed to set off Rachel who came again, a joint climax rewarding us both. Mrs X sensed the end and moved to stand up, but I held her down, preventing her from moving.

"Your work isn't quite complete maid. When I pull out of your daughter, I suspect a flurry of my cum will follow. This rug is exquisitely expensive and has to be cleaned by a costly expert. To avoid any soiling I suggest you attach your mouth to her anus as I withdraw to catch everything. Is that understood."

Mrs X played the part of the disgusted mother, but I could tell she was up for it. Rachel smiled back at me as I started to withdraw, clearly looking forward to the prospect of having Mrs X's licking cum out of her again. I had hoped we'd find a way to make it happen having discussed it in the car on the way up. As my still hard cock popped out of Rachel's arse, Mrs X and I were treated to a glorious view, that of Rachel's well-fucked gaping arsehole where we could already see a pool of cum just below the ring ready to be cleaned away.

I'm not squeamish about eating my own cum from Rachel, I relish it in fact, so I was slightly jealous of Mrs X as she pushed her tongue deep in my wife's bum. Both of them clearly enjoyed it as they both made happy moans as Mrs X tongues away at Rachel's ring, flicking the cum into her mouth like a hungry cat on a plate of milk. The view for me was what I describe coupled with the vision of Mrs X on all fours, her red arse exposed, her inner thighs glistening with her own cum and her hands pulling Rachel's buttocks apart as she rimmed away.

I left them to it as I quickly went to the bathroom to wash my cock in the sink before returning to the rug where I then sunk my cock into Mrs X's pussy. Rachel will have sensed what was happening as Mrs X groaned 'oh god that feels lovely' breathily into Rachel's cunt as I started thrusting and pushing Mrs X into my wife. I was surprised to still be hard after the enormous orgasm I had just received but either the Viagra or the situation was having a powerful effect on me. I was aware I had promised them both a hard ass fucking but, right now, I was happy to be pummelling away of Mrs X's pussy. As I fucked away, I develop a narrative that I could cum in her pussy telling her I had no concern for her ability to be fertile given she was probably barren by now. I didn't want to upset Mrs X though and part of me started to wonder if I would 'knock her up' if I came in her. That would be awkward I thought but I swear my cock grew even harder at the thought of getting Tiny's mum pregnant and cuckolding Mr X in the process. Mrs X didn't help when she turned around, breaking the charade as she said, "fuck me Tom, this is the best night ever, fill me with cum, make me yours, breed me Tom, breed Rachel, breed your wife and mother-in-law."

"Do it Tom," Rachel added, "make us both pregnant."

I am afraid this fantasy was too much, and I let go another salvo of cum deep into Mrs X, both of us collapsing on to the rug as we came. I wasn't sure if that was it for my cock but, if it was, what a fine evening this was.

The room had gone a little cooler, so we soon gravitated to the bed where I now found myself with Rachel and Mrs X either side of me, both stroking my chest as we kissed or petted each other. Mrs X and Rachel started talking about what we'd just done, discussing how the spanking had hurt but that it was also such a turn on for them in the context of the fantasy we created. Rachel then took the conversation to how it the evening had ended, asking, "what will you do if you are pregnant, mum?" She added the mum with an exaggeration to again remind us of our dirty play.

"I'll claim hubby successfully tupped me on new years eve. He won't remember a thing anyway."

"You're serious?" Rachel asked.

"Don't be silly Rachel. I'm joking. I had my tubes tied after our last one. Besides which I think Tom would have made me a mum again the first summer we got together if I hadn't."

"It did make it feel more exciting though, didn't it Tom?" Rachel said as she leaned over to me.

"Oh yes," I replied, "very exciting."

Mrs X grabbed my cock as she added, "I seem to remember Rachel begging you to make her pregnant too. There seems to be a little life left in him yet so why don't you, here, let me witness you trying to make your beautiful wife pregnant Tom?"

"It must be the Viagra as I should be spent by now, but I'd love to Rach if you're serious?"

Mrs X and Rachel looked at each other knowingly and Mrs X touched Rachel's breasts saying, "I think you should tell him Rachel."

"There never was any Viagra Tom. That was just you."

"Seriously?"

"Seriously. I would never give you anything like that without your consent. Nor would Mrs X Tom. We both love you too much."

"Thank you, ladies, I love you both too. I have to say that's both a relief and an enigma. I've never felt so turned on and I'm hard again darling, mainly thinking about putting a baby inside you."

"Then make love to me Tom, let's make a baby."

~

Mrs X returned to her room at about 4 in the morning after witnessing Rachel have another huge orgasm as she welcomed my last climax of the night into her but not before sucking me clean. Rachel and I collapsed in each other's arms, not really moving until mid-morning the next day. I was relieved to see that her bum had returned to its normal pale hue in the morning as I stroked it as waited for her to stir.

After I'd added another chance of 'making her a mummy' we ventured downstairs to be greeted by the most fantastic breakfast. Mr X had apparently gone shooting so Mrs X asked Rachel if she would allow me to fuck her one more (not last) time before we returned home.

"Only if I can eat his cum from you," was her reply.

~

We were quite quiet on the first part of the journey home, mainly because we were tired, but that soon changed when Rachel said, "I found out Mrs X's name you know."

"Wow, what is it?"

"Lilith."

"Nice name. Unusual isn't it."

"How about, if we have a daughter, we could name her that?"

"I'm not sure. I don't think I want to confuse my daughter with some very saucy memories."

"Good point. How about Lilly then?"

We then went on to have a very practical, but lovely and exciting, conversation about how we were going to get ready for a baby. And that was how I will remember the start of 2000. Joy, joy and more joy. Tom and Chloe agreed to be Godparents, so we were lucky enough to see Mrs X again in September, but that's a story for another day.