Threesome with Friend - part 4

David has a very joyous Christmas... but suffers from a hard strapping along the way [continued from part 3]

 

After rescuing david's sexual performance by babying him into a nice cummy and then making him lick it out of Paula's pussy to give her a second O, we cleaned up and all gathered in bed where we discussed david's subby kinks. Paula was amused and gently teasing of david, surprised at many of the antics we had gotten up to over the years. Despite his recent sexytime explosion he nonetheless got hard during our conservation, a state that both Paula and I monitored with our hands. We determined to explore these kinks of his more tomorrow. Paula gave us each a kiss and said she'd leave the two of us to sleep comfortably, gathered up her clothes and retired to her bedroom.

Next morning was Christmas Eve. Paula and we had dinner with family but we were in all day. David and I were just getting breakfast ready (bacon and eggs) when Paula came down in her robe. I have rarely seen her without her heels, and padding around in her bare feet she was short and cute. David and I were both dressed in everyday clothes.

"That was fun last night, you guys" she said as we hugged and kissed. David and I agreed. During breakfast we did not particularly discuss sexy stuff, but Paula in her robe, looking like nothing was under it, did flash a bit of "accidental" boob (ha ha - I know attention grabbing female behaviour when I see it!). So there was a sexy undertone for sure, as if we might break out into another threesome orgy at the drop of a hat. It was sort of kinky/sexy having her in just her robe, next to naked, with David and I dressed. She did not seem to mind or be at all self-conscious in the least. She seemed to want to make David a bit uncomfortable, in fact, in a seductive way.

Paula did not refer to david's "failure" at all. We had talked about it last night. How, while it was a sexual failure for him, that he was not much of a cocksman, but neither of us were that fussed about it. That didn't mean that in the moment he was not acutely embarrassed, and continues to be. But the embarrassment of his "performance" provided fodder for our Dominance/submission games. Paula, by now, knew all that from our bedtime discussion the previous night, and it was not rehashed that morning. Paula seemed to have lost no respect for him, judging by her attempts to seduce him, anyways

Paula went to get dressed and re-emerged a bit later wearing designer jeans and heels. David went off to do his thing, and she and I gabbed and gabbed, and we did our own things as well. We gathered again for  lunch. David made us his signature Italian sandwiches with focaccia bread, drizzled with top notch olive oil and balsamico, sun-dried tomatoes, eggplants in oil, bufala mozzarella, fresh tomatoes, and good prosciutto, toasted. A little Chianti with. So good!

After lunch I shooed David away and Paula and I conspired to give him a good double-domming. I told her what I was thinking of, and she was all in. Paula was definitely fascinated/interested and I did not need to push the issue at all. We decided we'd keep the theme from last night and "punish him" for his poor sexual performance. We had discussed strap-on play the night before, and I suggested that part of his "punishment" would be to take it up the ass from me while Paula watched.   Paula asked if it wouldn't make more sense for her, "the aggrieved party", to do the deed? She said she had heard of it, from more than just us yesterday night, but had never done it before and asked if she could give it a try. Yes, absolutely! Even better as far as I was concerned. I could coach her for her "first time", losing that kind of virginity. I'd be honoured. All girls should try it, much less those in their forties already.

Once we had the outlines all laid out, I initiated the roleplay: "David! Come downstairs please. Paula and I have something to discuss with you." We heard the TV turn off and David come down.

Paula and I sat side-by-side in the living room and we had David stand facing us.

"This is about your sexual performance last night. Or rather your lack of it."

"Yes Ma'am. Sorry Ma'am."

The cool thing with David is that we have played so much together that I don't need to explicitly discuss a scene with him, but can appear spontaneous. I'll nail his kinks.

This particular one is a special kink for him that we've played with before: sexual performance failure. He was in high school when he first embarrassed himself by cumming in his pants while kissing a girl in her basement.

The girl had noticed, was a bit weirded out, and asked him to please leave, which he had to do with cum-soaked undies and stained pants. David was too embarrassed to talk to her again much less ask for a second date. And, he was quite sure she had told at least her best girlfriend based on their giggles and a quick comment.

That can leave emotional scars on a high-schooler!

Throughout our relationship he was always a bit of a premature ejaculator. I didn't mind at all as I appreciated his ability to cum easily and fast, and vaginal intercourse never gets me off (it's good foreplay, but I don't need a lot of it). As he's aged he's developed more stamina, but when he's very excited he still cums fast.

Last night, losing his erection, was a new one for us. I think it was the unfamiliar rubber combined with performance anxiety over fucking Paula. There's nothing wrong with his erection otherwise. When he finally did penetrate Paula, it was all too much for him and he came very quickly. I have often teased him about his "cocksmanship" over the years as readers from this blog will attest, and while embarrassed by it, it isn't anything overly serious for him or me, so good play fodder.

"Here was Paula, who heard about what a nice cock you have from me, gracious enough to allow you to fuck her, and then you embarrass me like that and leave her completely cock-unsatisfied. Isn't that so, Paula?"

"Basically. I hadn't been fucked by another guy for years, and I was going to do this for you guys, and then you totally lose it before you can even stick it in. I mean, how pathetic? And then when it's finally coaxed back to life, my nipples are sore from all your sucking and I needed to use lube for my pussy. I never need to use lube for my pussy. And then when you're in you cum in, what, thirty seconds? Thank God you have a decent tongue or you'd be totally useless."

Perfect! I had coached Paula on laying into him as part of our "roleplay" and she really delivered.

I picked it up: "Remember how I said I'd give you a strapping if you lost your erection again? Well, while you didn't lose it again in that sense, you lost it well before Paula was satisfied so I think Paula and I will give you the strap, and then Paula will show you what a real fucking is."

david looked a little surprised at that. Maybe a little excited. Maybe a little embarrassed. He was not counting on Paula "doing the deed". But it was sooooo "punishment fits the crime".

"Now, go upstairs and shower and shave your genitals and ass crack, and clean yourself out to be ready for a long hard fucking. If there's any mess at all when Paula fucks you, you'll get the caning of your life on top of a strapped ass. Are we clear? Then you come back down here in your punishment outfit, and make it quick."

"Yes Ma'am!"

I knew the threat of the caning on top of his strapping would scare him. A caning for him in our house means the Delrin cane, which is the worst. I was sure his ass would be very well cleaned out.

David went up. Paula asked, "what's his punishment outfit?" We had not discussed that at all. Not even the night before. She needed some surprises.

"I'm not 100% sure. I guess we'll find out what he thinks it is." In fact, I was pretty sure what he would choose (coming down in nothing but a pair of panties as his "punishment outfit"), but I did leave it to him to decide. I thought it was a bit extra meta-embarrassing for him to pick his own "punishment outfit" for our scene.

After maybe 30 minutes or so david came back down the stairs and entered the living room wearing something quite unexpected. Instead of just being in panties as I expected, he was wearing white socks, a schoolgirl skirt, a plain red form-fitting athletic shirt, what was clearly his bra and falsies under it, and a giant blush! He could have chosen anything as his "punishment outfit" but chose this. Paula and I both appraised him as he walked in. Paula had a lovely smirk.

Well I was going to have to have some fun with this!

"That's right david, I hope you're embarrassed. Don't you think your punishment attire is particular suitable given your inability to perform as a man last night?"

"Yes Ma'am," david said.

"Use your girl's voice," I prompted him.

"Yes Ma'am," he repeated, an octave higher.

I stood up, took him by the ear, and conducted him to the corner where I pushed his nose deep into it. "You stay there while I fetch the hairbrush and strap," I said.

I left him there with Paula as I went upstairs to grab the hairbrush and the strap. I heard Paula start in teasing him a bit, about how cute he looked in his short little schoolgirl skirt, and what great little tits he had! Underlying the obvious was the fact that Paula knew that I had not told him to get into this costume, but that he had chosen to present himself to us, and specifically her, like this. When I was upstairs, I had an extra evil thought, and brought a couple of more things down with me. I mean, given Paula's playful reaction to his girl's clothing, why not take it a step further?

I got back and put the implements down on the coffee table.

Sufficient to strike fear into the heart and butt of any little girl!

I also put down some lube and a box of tampons.

Yes, I had decided he would be subjected to a very well-witnessed tamponing before I began his spanking.

"Oh my," said Paula, "A box of tampons. Is one of those going inside of him?"

"Yes. If he can't act like a man, I'll treat him like a woman. I mean, he's dressed the part already."

I'm sure david was positively cringing in the corner from the humiliation. Yes, he, as do I, gets turned on by humiliation, but the humiliation is still there. Needs to be, in fact.

I went to fetch him from his corner, again by his ear, and frog-marched him over, pulling strongly out and down. I led him to the back of the two-seater couch and had him bend over. I flipped up his skirt revealing that he did indeed have panties on under it, as expected. Of course they were his favourite yellow polka-dotted pink lacy panties.

"What pretty panties!" Paula said.

I pulled them down to just beneath his bum cheeks. I asked Paula to pass me a tampon and the lube. This she did. I then asked her to grab some paper towel from the kitchen, which she did as well.

"Could you... spread his cheeks, please," I asked Paula. She went beside him, leaning against the couch facing me, and spread his cheeks with both hands. She had a closeup bird's-eye-view of his spread asshole and would see every little detail of his anal violation with my tampon. I was happy to see his crack and anal entrance was scrub-brush clean with nary a hair in sight, but maybe a bit irritated at the thorough treatment he had given it? I praised it for him in front of Paula, and she agreed it was very clean, but did look a bit irritated, and very tight. I assured her it would open up like a flower to encompass a strap-on dildo the same size as his erect cock. She said, tongue-in-cheek, that she found that hard to believe. I told her that she should wait and see, as seeing is believing, not that there would not be some considerable pain involved, but nothing he was not used to, and nothing he did not deserve.

I applied lube with my fingers to his hole and pushed some inside. I went deep and used my finger to massage his prostate. He let out an involuntary moan at that.

"Oh, he does like it up the bum!" Paula said with glee, staring intently at his bumhole clenched tightly around my finger.

I pulled my finger out then lubed up the end of the tampon, stuck it into his butt until my fingers on the grip would go no further, and pushed the plunger home to seat the tampon. I pulled the applicator out and voilà!

"There we go, little miss cotton-tail," I said as I wiped my hands of the lube, pulled his panties back up, and flipped his skirt back down. I had him stand and face us. He was blushing. Yay!

"Now you know what it feels like," Paula said, unsympathetically.

I walked into the kitchen to toss the towel and wash my hands, and then returned to the center of the living room and put a spanking chair there, back to the fireplace, facing the couch where Paula would be sitting, with the coffee table and implements between us. I asked Paula to bring "her" over to me, "by her ear". Paula had perfected her little smirk, reached and took his ear, gave it a bit of a twist which elicited a little yelp from him, and pulled him over to me. I took his other ear and brought him down across my lap as Paula released him. I directed Paula to take a seat and watch a naughty girl being spanked.

Paula was delighted by all this. Clearly having fun with it. But honestly, maybe it's because I pick them carefully, but this is the reaction I see from most women when seeing this sort of thing for the first time.

I started rubbing his butt over his skirt. I said, "You're not really much of a man at all, are you, sweetheart? You're dressed like a girl, you have a tampon in you like a girl, and now you're going to be spanked like a girl, and then later fucked like a girl." I lifted his skirt and smoothed down his panties.

I began spanking him with my hand over the silky material of the panty. Pausing now and then to pull them up taught against his butt. "This is what you're good for, isn't it? Being put across my knee and spanked in your pretty pink panties like the naughty little girl you are."

I spanked him a bit more and then said, "now stand up, young lady. Let's get that shirt up and these panties down." He stood. I raised his shirt up until it was above his bra.

"Oooh. Pretty!" said Paula. It was pretty. It was his pink Victoria's Secret number.

Exactly this model

I then had him hold his skirt up as I slowly pulled down his panties and banded them around his knees. Out popped a giant boner. "Just look at that!" I said in disgust, indicating his erection.

"Where was that at the moment of truth?" asked Paula

"Exactly! I said. "He can get it up when dressed and tampaxed like a girl and about to be spanked and fucked like one, but where is it when he's asked to act like a man? Nowhere! Now get back across my knee. I will guarantee you that you won't have that erection after I'm done with you."

He went back awkwardly across my knee and I resumed spanking him, this time on his bare bottom. "This young lady needs more than just my hand to make an impression on her bottom. Would you pass me the hairbrush, please, Paula?"

Paula sat up, took the hairbrush, leaned over, and handed it to me. I laid it on his bare rump and rubbed it around a bit.

"Now, Paula, don't be alarmed if you see this little girl crying like a Banshee across my knee. She'll kick her little legs, cry out, maybe even beg for me to stop, but she has a safeword she can use if it's too much for her. Isn't that so, honey?"

"Yes Ma'am." He remembered to use his girl's voice this time.

I raised the hairbrush and smacked his cute rump, hard!

"Ahhh!" he cried out.

I started into a rhythm of medium hard smacks, rising and rising in intensity. As always with this hairbrush it didn't take too long until his ass was a bright cherry red and he was squirming and howling and begging, "no! no! no! please! Owww! No! I'm sorry! Please!" david really "let's it go", especially in front of another woman. He gets off on the humiliation and so allows his vocalizations to come readilly to his lips.

As the spanking went on and on his panties worked their way down to his ankles and then off one ankle, and then off the other. I usually like spanking until he's fully lost his panties!

I turned him and made him straddle my left leg as I hooked his left leg with my right. This of course turns his ass more towards Paula on the couch and spreads his buttocks more and puts both his junk and his tampaxed bumhole on display, like this:

I put the hairbrush down beside me and used one hand to part him wider and the other to spank the more sensitive inner parts along his ass crack and high thighs. Of course, this also emphasized the girlish tamponing he had received, with the white tampon string very visibly dangling out of his clenched-tight ass hole. I also very lightly slapped his balls and a bit harder, his cock.

"Would you like to take him across your knee?" I asked.

"Sure," she said.

I stood david up and Paula came to sit in my place. I had david lie back across her two knees in the more traditional way. She had a bit of trouble balancing him at first. Ahhh, experience! But they eventually managed a tenable position. I picked up the hairbrush and went to sit on the couch to watch.

She started off by rubbing his butt, tapping it lightly a few times, and playing with his tampon string.

"How does that feel up in there?" Paula asked as she wiggled and gently tugged on the string.

"embarrassing..." david replied weekly.

"I'll bet it is."

Paula looked at me, and shrugged, and gave him an open-handed slap on his bottom-cheek. It was pretty weak.

"You can go harder than that," I said.

She steeled herself, tightened up her hand, raised her arm, and came down with a much stronger smack.

"ow!" david said, encouragingly.

"Ouch! That hurt my hand!" Paula said.

"Here, use this," I said with a laugh and handed her the hairbrush.

She took the hairbrush and began smacking it down. She went all over the place with the brush, but not very hard, fortunately. I got up and gave some remedial spanking instructions showing her the best places to smack him without fear of injury.

When she got the rhythm and aim going correctly I told her to go harder, as she was really holding back. She gave a harder smack and david gave a little yelp. "Oops! Sorry!" she said, as if she had not just seen me spank the crap out of him!

"Don't apologize to him. Think about how angry you were when he lost his erection just when you were expecting something."

"But I wasn't angry, I felt sorry for him," she said with a giggle.

"Well, for my sake he needs to know there's going to be consequences if he can't keep it up."

"Yes Ma'am," Paula said, mimicking david's address of me.

I then watched with more satisfaction as Paula increased the intensity and gave david at least a semi-proper hairbrush spanking.

In my experience, there are two sorts of newbie spankers. Ones who go WAY too hard (that was me after the first few moments!), and others who really can't bring themselves to spank hard at all, no matter what. Paula was closer to the second category.

"All right young man, that's enough of the hairbrush for you. You still have the strap coming."

I picked david up off Paula's lap and conducted him over to the back of the two-seater sofa. His bra-clad tits were still jutting out beneath his raised shirt. His erection was still there, and I was acutely aware that I had promised it would be gone before I was done with him. I bent him over the back of the sofa and then flipped his skirt up. His panties were of course long gone. I picked up the strap and went to stand behind him, indicating Paula should do the same. I lined up the strap and whipped it into him with a loud crack that got an immediate reaction. "Owwww!" david cried. And we could literally see a strap mark come out.

I started to explain to Paula the mechanics of the strap, and how it's the end of it that flies the fastest and does the most damage, but Paula cut me off and said she'd leave the strapping to me.

Ok. I told Paula to go around to the front of the sofa. to kneel down in front of david, and to hold both his hands in hers. I told david to look at Paula in the eye as he received his strapping. I love doing this when another woman is involved. It's a little fetish of mine. It turns me on to know his palms will be in her hands as they start spasming from the pain and sweating, and his pleading eyes will be looking deep into hers as the tears inevitably come. In fact, I was starting to soak my panties at just the thought of it.

Paula noticed that one of david's falsies had fallen out when he bent over the couch and she gently put it back into place for him, then took his two hands in hers, and they looked at each other in the eye.

I pulled the strap back and whipped it HARD into his butt-flesh. David let out an "Arghhhhh" sort of grunt and Paula looked a bit susprised.

"What's your safeword, david?" I asked him.

"It's 'red' Ma'am."

That was to remind Paula that he was consenting to this.

I pulled back and strapped him as hard, or maybe even harder, again. I then took up a rhythm and proceeded to give him a proper, erection-destroying strapping that he would not soon want repeated.

After maybe a couple of dozen very hard, full swings I asked, "What do you say, Paula, has he had enough yet?"

"Yes. Definitely."

"Ok then, just ten more."

"Nooooo!" david cried, beleiving it was over.

"Hold him tightly, Paula, he needs this. david, if you break eye contact with Paula, or pull your hands away, I'm starting your ten over again from the beginning. Paula, you let me know, even if he's on number nine."

"Ok," she told me. Then to him, "It's only ten, you can do it," she told him consolingly.

I made them slow and hard, and did not spare his high thighs. I could see Paula wincing and grimacing at his treatment. I don't know what gets into me sometimes. This should have been over long ago, given Paula's apparent discomfort level at this stage, but something in me just wanted to beat my husband just then, you know? I get a bit possessed and "glassy eyed" I am told, when I am delivering a good beating. Paula confirmed that look in me afterwards.

Paula counted the strokes for him, counting down: "just nine more, you can do it. Just eight more... Just one more. Hang on."

The tenth is, of course, the hardest stroke of all.

"Did he remove his hands or look away at all?"

"No, he was holding on and looking at me the whole time."

"Are there tears in his eyes?" I knew there were, from the sniffling, sobbing sounds, but I wanted her to confirm out loud, that this "man" was reduced to tears under my strap.

"Yes," Paula confirmed.

He had cried in front of Paula, while looking at her straight in the eyes so she could see the tears forming. There was the acrid smell, the sharp tang of released endorphines and adrenalin mixed with sweat. He had a sheen all over his visible skin. His ass was a mess. It was heady. I knew it was more than enough for him, as he had the option of pulling a hand away or breaking eye contact with Paula to get more, but he didn't. I thought it a pity that he did not just glance away a bit to see if Paula would have ratted him out. But I guess he was taking no chances.

"Come around here and see the damage," I told her.

She came back and saw the deep crimson red overlaid with the strap welts and winced. I had her touch his hot red butt and trace his welts with her fingers.

"Wow..." she said, a bit impressed I thought.

I had david stand up. He did so painfully, clutching his bottom and high thighs.

Worse than this.

I flicked at his soft penis with my finger. "What did I tell you?"

I then said, "tell Paula why I spank you."

"Because, I asked you to, and I need it every so often."

"Do you want it as hard as I gave it to you. Do you need it that hard?"

"Yes Ma'am, every now and then."

"When was your last really hard spanking?"

"Too long ago, Ma'am."

"Thank Paula for spanking you and watching you get spanked."

"Thank you Paula."

"You're welcome, David." Paula said in a soft voice. "It was... an experience."

"Do you still feel bad about your performance last night, in bed with Paula?"

"Yes Ma'am"

"And what would make you feel better about that?"

"If... if... P...p...paula were to... ummm... f...f...fuck me in the ass the way I should have been able to fuck her?"

"Are you still game, Paula?" I asked her.

"Absolutely."

Oh goody, she was not put off too much by his beating.

I turned to david and said, "well let's get you upstairs to the bedroom and get you fucked properly, young lady, so you can learn how a cock can be used to teach a girl her place..."

[continued in part 5]