Mother May I...? Ch. 06

Story Info
Continuing as we mean to go on.
7.2k words
4.79
3.5k
6
0

Part 6 of the 8 part series

Updated 06/15/2023
Created 04/06/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

(Authors note: This chapter contains homosexual activity... Run for your lives!!!)

Mother May I..?

Chapter 6

Continuing as we mean to go on

*****

"So what do you say Ade? You want to have a drink with me?"

Standing at the bar, Adrian felt like he was in another world and hearing Greg ask what turned out to be the magic question... Would he like to have a drink with him?

Would he indeed...

"I... I'd like that Greg b-but you know I'm not... You know? I'm not sure if that's what you mean? Or what a 'drink' means" Adrian replied, being cautious but wanting to understand...

"Hey it means whatever you want it to Ade. I just wanted to talk for a while, say hello. You don't need to feel pressured, I just miss my old friend, that's all" Greg said back wanting to put Adrian at ease, saying he didn't need to torture himself wondering if one thing meant another, like did a 'drink' mean sex?

"Yeah uhh, sorry I tend to do that, over think stuff but umm, yes, I'd love stick around and wait for you, I... I missed you too Greg. I always wondered what happened to you. I figured you were still out west but when we came in here, I didn't know what to think, so... I'm sorry if I seem surprised, and, and especially with Ma'am and Miss Denise being here as well... I'm sure you must think I've turned into some kind of a freak"

Carrying on, first saying how he would love to stay and hang out with him, Adrian in his nervous state also admitted to missing Greg and then calling himself out for looking as he did, and who he was with... He was trying to preempt his own humiliation by owning up to it, be depreciating and in using a corny old phrase, he wanted to 'head them off at the pass' if he could...

"Hey like I said, we all have our thing and I don't judge... Even I have my own kinky way of doing things, but listen, I have to run, we'll talk about this later yeah? You can tell me as much as you like, and I'll do the same" Greg replied ending their first rather revealing conversation...

*****

Back at the table...

"So? What did you two talk about? Tell me he's asked you out?" Margaret chirped sounding excited, sat up in her booth seat when seeing Adrian make his was back and smiling himself, he did seem to so much walk back to the table as he did float across the floor...

"No... Well, not really but he did ask if I wanted to stay after we eat and go have a drink with him... Just to catch up... Before you start thinking anything else" Adrian replied knowing both woman would be all over him like a Parana on a fleshy bone...

"Oh yes, a drink you say?" Margaret teased, unable to hold back but smiling she did know where to draw the line..."Oh I'm only joking with you, I think it's nice, even 'if' nothing were to happen, which I highly doubt, but still, and like I said before, I think this changes things"

"Ch-changes things how?" He asked, curious as he sat in the booth beside her taking up his seat and also seeing his meal had arrived...

"Never mind, I'm just thinking out loud, I'm actually quite happy for you Adrian, now lets eat so Denise and I can get out of your way... Goodness knows we wouldn't want to crash your date"

"Yeah Adrian, I'm happy for you too... Who knew this would all happen so fast huh?" Denise added as Adrian gave her a slight smile while thinking the same thing... This was all happening rather fast... Too fast in fact...

"There's nothing to be happy about and please, this isn't a date either... I didn't know he was going to be here but I am going to stay. What I don't know is how will I get home? I don't have any money" Adrian replied...

"Don't worry about that, you can charge an Uber to me, but something tells me you won't need it" Margaret answered smiling again as she tucked into her meal with Adrian left to do the same but looking to her none too impressed...

*****

After dinner...

"Okay I'm back, sorry that took so long. We're having a big party here next week, hey you guys should come, it's a costume party for April Fools Day... I'll put your names on the list" Greg said as he came back to find all three still there, Margaret, Denise and of course Adrian...

"That's alright dear, we were just finishing our pie, you have a lovely dessert menu and it seems I have a bit of a sweet tooth, but I'm sure you know how it is? When you see something so pretty and sweet you just can't resist?" Margaret replied, flirting with Greg the 6-ft tall cool drink of water, dressed in black and looking quite sexy as she gave him a wink while at the same time tilting her head towards Adrian, indicating to him, to witch Greg smiled back with a chuckle...

"Yes, I know just what you mean... And don't worry about indulging yourselves, it's on the house... This time, because you will come back, yes?" He asked as Margaret made a move then, having Adrian stand to let her out of the booth and preparing to leave...

"Come Denise, I'm sure these two don't want us hanging around gawking away... They're probably more interested in getting on with their date" she said to the girl as she rose up as well, beaming with a big smile, nodding along and acting her happy, bubbly, 20-yr old self...

"Thank you again for you hospitality Greg, and we will take you up on your offer, I'll have my own pretty little thing do her magic on the computer and book us a table... Now as for you... I'm sure I can trust you'll return my other little pretty thing here back to me all in one piece?" Margaret asked giving a second nod Adrian's way before adding... "I'm sure his wife would appreciate it, wherever she may be"

Cringing, Adrian could feel himself blushing as he rolled his eyes, praying this would end, hearing her refer to him as her 'other-pretty-thing' then mentioning Barb once again, being sure to point out her absence and what that may mean...

"Oh don't worry... I won't keep him out too late and thanks for looking me up, I'm really happy to see my little buddy Ade again, it's been too long since we've been apart... What is it now Ade? Like 15yrs or even longer?" Greg replied, assuring Adrian would make it home as he turned to him then, asking how long it had been since they last saw each other, or 'since we've been apart' as he said it...

"Well, we'll leave the two of you to figure that out, and here... You may need these" Margaret said, interrupting and wanting to be on their way, but thinking, she stopped and reached into her hand bag to find the small ring containing the keys to Adrian's chastity cage making his eyes go wide with fright, seeing what she had in her hand and where in a panic, he lunged towards his Mother-in-law quickly snatching the two silver coloured keys from her hand...

"I'll... I'll take those" He said nearly shouting, clutching the ring to himself but form the look Margaret gave him, he knew this little move was going to cost him as Greg watched, smiling yet somewhat confused...

"Uhh, okay! Whatever that was... Thanks you again for coming, it was a pleasure meeting you both, and please don't worry, I won't keep him out late. I'll make sure he gets a taxi home" Greg said, a little surprised with Adrian grabbing whatever it was from the woman, he hadn't really seen, but letting it pass, he thanked Margaret and Denise for coming before making a move himself. Taking the woman at her elbow, Greg was the one to usher Margaret out this time, also wanting the pair to be on their way...

"You be good now, do what ever Greg tells you" Margaret said to Adrian as a final good bye, giving him one last warning and for whatever that should mean...

"Oh I'll be good, and I don't think I'll be too later either, and umm, thank you for, for... You know? Everything?" Adrian replied while thanking Margaret but doing so in a way that he hoped she would understand. Talking about her giving him the keys to his cage, he wanted to be sure she was okay with it... Okay with his being let out...

"Your welcome too Adrian and yes...yes you may... See? I'm not a complete ogre... We'll talk more later, now give us a kiss and we'll be in our way" she replied smiling as Adrian then he leaned in to kiss her cheek as a show of thanks and his respect.

However with the way he was feeling at that moment? Being permitted out of his cage, Adrian was so overjoyed, and had they not been in public? He would have been on his knees kissing Margaret's big beautiful ass instead of her cheek...

*****

Outside and by themselves, Denise looked to Margaret asking, "Really? You're going to let him out?" she said as the woman stopped for a second on the sidewalk before continuing with a new smile coming to Margaret's face and looking straight ahead, confirming she replied...

"Yeah sure, why not? Like I said earlier, this changes things"

*****

Not too long after...

"You know the first guy I hooked up with in college? He reminded me a lot of you. That's kind of why I went for him, I guess he felt familiar, and the things we did, well... That felt kind of the same too" Greg said to Adrian as they sat in a different bar not too far from Woody's but still in the district, the scenery was no different, and neither was the mood...

Leaving Woody's, Greg had led the way with Adrian at his side and doing most of the talking, he felt no need to beat around the bush, being out as long as he had Greg was well past feeling any need to hide, or as Adrian listened, his old friend didn't feel all that much need to be discrete either...

"Really?" Adrian said back, surprised and even embarrassed some with Greg 'going-there' pretty much right away, or as soon as they sat down...

"You were uhh...my only, uh, guy" he stuttered out not feeling quite as free or 'liberated' as Greg seemed to be. But admitting as such, he went on to clarify...

"Actually... I can't believe I'm saying this but uh, after you left for university, there wasn't anyone else, not until Barb came along. My wife Barbara that is... She was the one who approached me, I... I was too shy" Adrian said, stumbling out his words nervously trying to let Greg know that after him, after he had gone to University, Adrian hadn't just stay away from guys... No, and as it seemed, he stayed away from everyone.

Or more like it was girls... They stayed away from him...

"Oh hey, that's okay, better late than never right? As you know I slept with a ton of girls in high school but I was never really into them" Greg added, letting Adrian know that being a virgin until he was in his late twenties was okay, but then reminding him of all the girl's he'd bedded in his early years, Adrian had to let his eyes flick away, feeling the jealousy or envy for his older friend creep back in, just it had in the those days long gone by...

"Yeah, uh I guess that's why we uh, you know? Why we started messing around" Adrian replied, nervous and still stuttering but as Greg noticed, he wasn't so much as shying away from the topic of 'them' either...

"Yeah, I'm sure it was" Greg confirmed, positive the experience was the turning point for him...

"That first time out in the hydro fields? I'd never felt more right about myself as I did then. It was like a light bulb went on in my head, or it woke me up at least, but I'll also admit I was sort of in denial... Remember how we didn't talk for like a weeks after that night?"

Going on, reminiscing and remembering Adrian was learning for the first time how all of this had effected Greg, which made him feel not so bad about his own experience, hearing that his friend had also struggled with what was happening, it put Adrian at ease in a way...

"Ye-yeah, I remember" he replied, telling his side of things... "I thought maybe you were embarrassed and didn't want to be friends anymore... Ha-ha!" Adrian replied but then laughing suddenly at the end he caught Greg's attention as he perked up, looking to him curiously...

"What's so funny? He asked and smiling himself, he wanted in on the joke...

"Well, it's weird and sorry for laughing but back then? I thought you wouldn't want to be my friend anymore because you must have thought I was gay, after, you know? Doing 'that' for you? But in the end, it was you... You're the one who turned out to be gay, not me!"

"Ahh! Hey yeah that's a good one, I guess you got me there, but remember! I was the one who had you, right?" Greg replied after sharing the laugh and the irony, but then saying he was the one who 'had' him back then, Adrian was looking confused and unsure. Was he still just trying to be funny, or was it more like he was making a point?

"Umm, I guess" was about all he could say, thinking he understood, but not really...

"What I mean is, and don't get me wrong but I was the one who had you going down on me, and if I'm going to be completely honest, you sort of set me on a path, or like I was saying earlier, we all have our kinks, right?" Greg added but confusing Adrian further, and seeing it in his face, he felt he should go on...

"I'm trying to tell you is, that having you blow me and not have to do anything with you in return, because let's face it, that's how it was with us. But anyway, that sort of set things up for me. I liked it that way, having a younger guy or maybe just someone less secure, I liked coaxing them into it, or seducing them I guess you could say... I'm what's known as a top, if that means anything to you"

Hearing his old friend, and admitting to himself this was 'how it was' between the two of them, because he was right, at no time did Greg offer or even make a move on Adrian, like grabbing his tight little ass in the pool hall when no one was looking. It was always Adrian giving his silent acceptance, a simple nod each time Greg had asked...

For the pair of them, it was always a one sided affair. Except of course for the last time, a few days before Greg went away when Adrian had bucked up the courage to ask in a meek, shy voice as they sat in his car with him saying... "Did you want me to?"

Which coincidentally was also the last time they would see each other... Until today...

But now, with Greg saying he was a top and he liked 'seducing' younger, weak willed guys like him, or 'because-of-him'... Hearing this did send an extra shiver running down Adrian's back, seeing now how he had influenced Greg in his choices, or preferences one might say. It also made him feel as Greg was describing, not so much saying Adrian was a 'bottom' but knowing now how his old friend perceived himself, the logic was there and bright as day...

Adrian was without question a submissive when it came to sex and relationships, he was a bottom all the way...

"You know I think I'm the same way, but reverse... Keith hasn't ever touched me like that either" Adrian said next but then catching the error of his ways and looking to Greg, he knew it was too late and he was going to have to explain...

"Yeah, so if I can ask? What's going on there?" Greg did ask with Adrian sinking in his lounge chair set at the back of the bar in a quiet corner away from the noise, he thought for a second wondering where to begin but then and being rather good at it so far, Greg filled in the blanks for him and essentially hitting the nail on the head...

"No wait, let me guess" He said as Adrian stopped with his mouth hung open and about to talk...

"You guy's are in a cuckold relationship right? And this Keith fella, he's your wife's ex-boyfriend and when you guys are together he, or they have you do things? With him?" Greg asked and of course about all Adrian could do was nod with his jaw on the table, however amazed really, he did feel the need to ask...

"How? How did you know that? I mean, I guess Ma'am, or uhh Margaret, she wasn't much help" Adrian asked but adding insult to injury, Margaret was Greg's next port of call, wanting to know what was up with her as well...

"Yeah and what about her? You Mother-in-law is a real sex freak huh? Having you looking so aah, 'pretty' let's say, and her girl friend? Denise, she looks young enough to be the woman's daughter" He commented while also asking, as Adrian once again he was a little lost for words, but given a second or two he was able to explain this part of his weird new life...

"She wasn't always like that... I mean, I know she never liked me much before all of this started last Christmas... To make a long story short, Ma'am, as I'm suppose to call her, she overheard Barb and I taking after she slept with Keith the first time on Christmas Eve... It was an accident and I believed her, I was drunk and went home and..."

"And she stayed behind for a night cap, right?" Greg said, knowing already and sparing Adrian the agony, he knew what was happening, because as they say... This wasn't Greg's first Rodeo... Not as far as the area of sex and sexuality were concerned...

"Yeah, you seem to know an awful lot about this stuff, don't get me wrong though, I like how you know things already, it makes it easier to tell you I suppose, and yeah, that's exactly what happened b-but the other stuff, that didn't start until after they went away together"

*****

Talking now, or more like spilling his guts, Adrian went on to tell Greg the whole sorted story of how he ended up in his Mother-in-law's clutches as well as how he found himself sucking Keith's big dick to either get him hard or as Barb had caught him, sucking her boyfriends cock for the pleasure of it...

"Wow! So the keys Margaret, or 'Ma'am' as you call her... The keys you took from her, they open your chastity cage I take it? That's why you were so eager to snatch them from me? Because if I remember correctly, she was about to give them to me, wasn't she?" Greg replied, asking after hearing how Adrian's life had been evolving, becoming submissive to all three, his wife, her ex Keith and his Mother-in-law, Margaret the sliver-haired middle aged Dominatrix in the making...

"Yes... I was suppose to be in this thing for the next six months, it's, it's to stop me from masturbating... I don't why she handed them over but when I saw what she was doing I just sort of reacted... Why? Did you want me to give them to you?" Adrian asked while nervously taking the small key ring from his pocket as Greg looking intrigued and smiling from ear to ear, he was the one left nodding out his reply this time...

"Yeah I think she wanted me to have them, don't you? So let's go, hand them over, or you know what will happen" Greg teased, holding out his hand as Adrian, feeling playful he tested his old friend, asking him... "No, no I don't... What will happen?"

"Oh you don't want to know little buddy, remember, I said I was kinky like you, but believe me, my kink goes waaay deeper so, let's just say for now that feeling your Ma'am's belt heating up your ass? That will be like a day at the beach compared to what I'll do with you"

"Oh gosh Greg! Now you're scaring me but you're right, I think she wanted you to have them, but why though?" Adrian replied feeling weird all of a sudden, nervous now and somewhat excited, he wasn't sure if he should feel as he did just then. What with him professing his 'straight-hood' all evening, and now, being turned on all of a sudden, hearing Greg and how he was talking, saying his 'kinks' could out kink them all...

Handing the keys over, dropping the small set into his long lost friend's large, open hand, Greg smiled at him, telling him... "You're doing the right thing Ade, and hey if we're gonna use these keys like your Mother-in-law was intending, what say we get out of here? I don't live too far away"

Hearing him and biting his lip Adrian felt a chill hit him, a cold forbidding in a way, both wanting but also he was afraid... Afraid of what it would mean and how this would not only prove everyone right, but again... Adrian was worried that if he let Greg take him home, he might discover more of the same lies he's been telling himself for far, far too long...

12