Dana-girl Ch. 01

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Mamma's boy.
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Part 1 of the 6 part series

Updated 06/10/2023
Created 01/04/2021
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Intro...

Having written "For Veronica's Sake" with no grand expectations concerning a response, I was however quite pleased with how well the story was received, liked, voted and commented upon (okay, some I deleted because I wont suffer fools)... Yet it was within those comments where a few suggestions came to me, thus leading to what we have here...

Now with that being said, I do wish to continue turning this into a "Beach-Get-Away" story, but for now, I have come up with what I'll call a "Mid-quel" or an interim written around and including some of the suggestions I've received regarding where some would like to see this story to go... I thought it was worth it, and maybe you do too...

Again, I Thank you again for your patronage...

Dana-girl

Chapter 1

Mamma's boy

"Your Mom has been texting me, she says you've been avoiding her calls" Veronica said to me as we sat down to eat. It had been a few weeks now and it was true, I had been avoiding my Mom, but honestly, who could blame me?

"Oh God, I was afraid of this" I replied feeling a cold stripe of fear running down my back... "I know, I have been out of touch with her, and yes, it has been on purpose, but before you get on my case, I'm sorry, but I just can't seem to find the courage to tell her about... Well, about everything that's been going on... You know? With me, and you? -and now with Reg?... I just don't know what I'm going to say to her"...

Answering I could feel the huge knot forming in my stomach. I had been putting off contacting or saying anything to my Mom, who growing up, of course she was always on my side. I knew I could trust her with just about anything, because after all, she IS my Mom... But still, this?... Something like this was a different kettle of fish altogether...

Telling her about what we've been up to, and the direction we see ourselves going, giving this 'polyamorous relationship' thing a try, or sort of anyway. I had to thinking and wonder how I would even broach such a subject like this with my Mom in the first place. I mean where would I even begin a conversation like that?

The idea alone had me cowering, and that's why like a bad tooth, I'd been trying to ignore the ache and the agony, hoping against hope that it would just go away on it's own...

But I knew this wasn't going away....and just like that bad tooth having to come out, needing to be pulled?... As awful as any trip to the dentist can be, I wanted telling my Mom about all of this to be painless and go easy... If that were possible...

***

It was late November and we were planning our trip with Reg to the Bahamas, yet for how long we were going to be away, that much was still to be decided... What with me able to work from my lap top and with Veronica taking a leave from her job, we found ourselves able to stay for however long we wanted, and to further us along, Reg had come to us with a suggestion that would cover our at home expenses while we were away on this extended vacation.

So together, and with his idea, we signed up to turn both of our places into Airbnb's''s while we were away, thus covering our mortgage and taxes for however long we wanted... It was a great idea that made everything all that much easier from a financial stand point.

However, and on a different note... Something else that had been happening was me slipping further into the cross dressing, but not out in public, I wasn't ready for anything like that, or not yet at least.

When home and around the house or in our fenced in grounds, I was comfortable enough to wearing some of the old clothes Veronica had given me, but for the most part, I was dressed up in lingerie and sexier. lacier panties when the three of us found ourselves together in our new king sized bed... Where as well, the sex, although it was mind blowing to see and be a part of, there were still a great many times where I was feeling left out.

Quite often I'd find myself watching while Reg and Veronica fucked right in front of me and sometimes when they were alone, however when I was there and allowed to participate, it was quite awesome, but still, it was always humiliating in one way or another, seeing how I had been relegated to being the 'fluffer' in our scene... Left either getting them both wet and ready to fuck, and then again, once it was all over I was back in there playing clean up, providing comfort and care with my tongue and my lips, more so than I was involved in actually fucking my own wife.

Which was hard to take on it's own, but again, once I was over my wall and getting into it, losing Veronica to him in this way, it was easier to accept...

That job however... The job of fucking Veronica I mean... This pleasure had most assuredly been left to Reg, pretty much right from the beginning, and had progressed to where I wasn't so much being pushed away, or left out for the most part, but rather I was taking up my role as the submissive cuckold, dressed in my panties and make-up, playing second fiddle to Reg Morgan the 'real' man in our lives and in our bedroom.

I had let my life-long friend and best pal usurp my wife, and our sex life to the point where on most of our occasions when we were together, I was left to wank one out beside them in the bed, watching while they fucked in this very lopsided version of a 3-way, or 'polyamorous relationship'...

***

"Oh I'm sure you can relax Dana, with what your Mother knows already, I wouldn't let it worry you so much" Veronica began trying to put my fears to rest...

"She loves you, and just like how you want me to be happy, she wants the same for you... You're Mom wants you to be happy, and she doesn't care how you get there, just as long as you find what you're looking for" She finished, answering and telling me that I shouldn't worry about what my Mom was going to think, because apparently she knew a lot more than I had realized.

I know about the 'love-and-happiness' thing with a Mother wanting the best life for her children... I mean that part was a give-in... But as most would agree, this situation wasn't usual or normal, in any way, shape or form...

This wasn't like I was telling her I want to change careers and be fireman or doctor or something like that... It just wasn't that simple, or at least not for me it wasn't...

"Wh-what does she know already?" I questioned hearing what Veronica was saying while feeling that familiar knot of fear forming in my stomach... "Other than seeing the two picture you sent her, which I still can't believe you did... But what have you been telling her Vee? Oh God... I have a feeling this isn't going to be good"... I added with my panic level rising...

"Seriously Dana... Relax would you? I told her about your work changing and how with you at home most days, I let her know that we've decided it would be okay if you wanted to play dress-up more often" Veronica replied with a cute smile and an up-turn in her voice.

She was sounding far too calm and comfortable about all of this for my liking... Telling my Mom that this wasn't just a one-off thing with her dressing me up and taking pictures, and how if I wanted to dress-up more often, it was okay, seeing how I was working from home...

"She was fine with you cross dressing, in fact she was more than fine"... Veronica continued... "Remember? She said she was proud of you in her text message" She added reminding me of this forgotten bit of truth, and I did find that strange because Mom had indeed said that she was 'proud' of me dressing up and acting like a girl, even saying I looked like the daughter she'd never had... I could only imagine where this was going to lead...

"I sent her the rest of the pictures when she asked if there were any more, that's when I told her about you being home and, sorry but I let it slip that you've stopped wearing men's underwear altogether, switching to your own pairs of panties instead"

Listening to Veronica telling me everything, about how she's all but outed me completely to my Mom as far as the cross dressing was concerned, I stood looking at her slack jawed and not believing her...

But then on top of this there was something else that was even harder to swallow, and that was knowing there was still another piece to this strange, 3-way equation, leading to the next burning question when it came to what my Mom knew, and didn't know...and that of course was about Reg...

"Oh God Veronica, now I am glad that I've been avoiding her... I don't know how I can face her, I'll be so embarrassed and, and what about Reg? I suppose you've told her all about him too haven't you?" I asked sounding as I was feeling, which was quite upset and I was growing more so by the minute...

"Now, now... There's no reason to take that tone, but to answer your question, that's a yes as well... I have mentioned Reg to your Mother, and do you want to know what she said?" Veronica came back, first putting me in my place but then looking at her as a sly smile appeared on her lips, I was left wide eyed and shaking my head...

"Well, first she told me I was very bad girl, and I thought for sure she was mad at me... But then after a pause, she told me that she wasn't surprised, and that with Reg moving onto our land, she even wondered if something like this might happen"

"Really? She... She said that?" I asked surprised with how my Mom had already considered this as being a possibility, thinking something might happen between the two of them now that Reg was here and more or less living with us.

This too was a bit of a bitter pill to swallow, first with her oddly being proud of my cross dressing, but now, assuming that with Reg in such close proximity to us, there was a possibility of him moving in on Veronica... It was all sort of un-nerving and all I could think was to wonder what my Mom really thought of me after all?

I mean, did she see me as Reg had said? Was she also seeing me as a soft touch, and someone who's always 'had a chick living inside of him' to paraphrase my life long friend?

***

Now, getting to my Mom for a minute or two... Although I was raised as an only child by both my Mom and my Dad, it was after I'd left and moved out on my own at around 18-or-19 years old when my parents decided to split up... First separating on a trail-basis which eventually lead to their divorce a few years later, with Mom reasoning to me that they had simply grown apart and that's all there was to it really...

So, just as some background, and to give you a general description of my 50-something year old 5-foot 6-inch tall Mom, or 'Ms. Page Powers' as she's known... With her sandy blond, shoulder length hair, she was still in good shape for her age, or what I knew of, seeing how I had never looked at my Mom as anything other than what she is to me... Which was just her, being my Mom...

But I suppose if you were to compare, I did inherit more of her delicate features, more so than anything I had picked up any genes from my Dad...

I'm only an inch or so taller than Mom, and we are both 'slight' in frame I guess you could say. Our face shape, nose and blue eyes are similar, which also lends to my being so 'passable' as Reg and Veronica keep telling me with encouragement each time they've seen me dressed.

Of course I don't have breasts, being a guy, I'm flat chested, and in no put down to my Mom, I'll just say that she wasn't 'blessed' like Veronica... With Mom's chest being rather small and not much more than what I would assume would be an A-cup at best, she was more like me in this regard... But again, I didn't see that as being something to take way from who my Mom was, because as I've said, that's not how I looked at her...

***

Continuing...

"Yes, she did say that Dana, and it shocked the hell out of me too! But once I knew she wasn't mad, I felt I could open up to her about Reg, and in the end she said that she's okay with how we've decided to take things... You know? With Reg moving in, and well, taking over more of the 'manly' role, but she also said she wanted to come and see for herself how you were doing... She wants to come and check on her 'new baby girl' as she said it"

"She? She want's to come over?" I stammered, not knowing what to say or think at first, but then catching myself I thought again went on, agreeing as usual...

"I... I guess that's alright" I stammered back... "We can have her over for lunch, but lets do it soon okay? I mean with Reg away, working in England, doing some shows over there... I'd just rather not have him here for this because I know Mom is going to embarrass me... I bet she even makes me show her what panties I'll be wearing" I answered telling Veronica that I didn't mind my Mom coming for a visit, but I was kind of glad that Reg wasn't going to be around, at least for this first time.

It was true about Reg though... At the time, he was away doing a few per-Christmas shows over in England, so I thought if we could get my Mom here soon, before he came back at least, I figured we could sort of ease her into this, instead of her coming over and seeing us all together as one big, happy 'threesome'.

However when I mentioned my wearing panties and no doubt being asked to show them to my Mom at some point, Veronica's face changed, going rather blank with her eyes flicking away...

"What was that look for?" I asked as she turned back, looking deeper into my eyes as she paused then placing her hand atop mine at the dinner table and giving it a squeeze but saying nothing as she rose and walked out towards the front hall...

Puzzled now, I could see her from where I was sitting, but what I hadn't notice was the garment bag she'd left hung on the coat rack...and even more worrisome was the look she gave me as she came back carrying the long silvery coloured nylon bag hooked on a finger, passing me as she made her way towards the stairs using her free hand to wave me over, silently signalling for me to follow...

"Wh-what's going on Vee? I'm not sure I like the looks of this" I said getting up and trailing after her up the stairs leaving the our dinner dishes sitting on the table...

"What's going on here, is something that your Mom suggested, or said she'd love to see, and it was also your Mom who had this delivered to me in work at the postal kiosk, so really...this has nothing to do with me" Veronica answered as she laid the garment bag out on the bed, using her two hands to open and slide the long zipper down before picking it up again, hooking her finger in the hanger as my heart began to race thinking and wondering "Oh God... What now?"

"Wh-what is it?" I asked frightened but indeed curious while stuttering as usual when faced with whatever embarrassing thing was about to fall on me...

"Well"... Veronica replied but said nothing else as she held it up, un-shouldering the satiny looking bag from what was inside, and where at first glance I felt a slight pang of relief seeing what looked like a simple, black coloured dinner jacket...

"Once you Mom found out that you've been dressing up more, she said she'd love to see you in a cute little French maids get up... She giggled a little, saying she'd love for you to serve tea to us some afternoon" Veronica added and yes, my jaw was indeed on the floor, hearing but not believing what she was telling me, or what I was seeing...

"However, I told her I didn't think you would go for something like that, I remember how worried you worry about me tarting you up too much, so told her no... But, I swear Dana, like not even two seconds later she sent me a picture of this outfit, saying it was classy, and well yeah, once I had a look, I thought it would be perfect for you too... Here, hold the jacket, I still have to get the wrapper off the blouse and the skirt"

"B-blouse and skirt? Wh-what?" I interjected as she handed me the jacket off the hanger and I took it from her without thinking, but clearly, I had heard everything that she had said...

"So this is some kind of maid's get up? Oh Vee, I don't know...and what do you mean she wants me to serve tea?" I asked feeling my guard going up. I didn't like the sound of this, whatever it was they'd been planning...

"Yes it's a blouse and skirt set, and wait until you see the blouse! Oh and it comes with this cute little black and white bow for your hair, but we have use your own stocking so I bought you a new pair in black...and your first garter set too! Which I almost forgot!" Veronica went on explaining and sounding quite happy, never mind how I was feeling, which If anyone cared, I was stood there shaking, terrified and generally scared shitless.

Holding the jacket in my hands and feeling like I was frozen in time, Veronica went to her top dressed drawer and pulled out and new pair of black nylon stockings along with a small Victoria's Secret bag, containing what I believed to be the garter she, or my Mom also wanted me wearing.

Yet once Veronica was back and had it all out on the bed, I was surprised to see that the garter, it wasn't the only thing they had for me to wear under this maid's get-up I was to be put into while serving tea...

"Here look at the panties she included aren't they darling? They come from your favourite store" Veronica beamed while teasing me picking up the new pair of panties chosen for me by my Mom this time, adding yet one more shameful pair to the ever growing multitude in my top dresser drawer...

"Oh Gosh Veronica, these panties are see-through!" I said back to her in a high pitched sigh, my exasperation made clear as she handed me the feather light pair of sheer, black and indeed completely see-through panties, that were also quite small and delicate looking, edged in lace, including the elasticized leg holes making them look sexy and slinky, and certainly something very naughty, if not completely wrong for a guy to be wearing...

"Yes, they are quite sheer, and look!" Veronica answered but going on then, she pointed out the next embarrassing thing I was going to have to deal with...

See? They match the sleeves of your blouse! Isn't this so pretty? I can't wait to see you wearing this outfit, in fact, here, get naked baby, lets have a little 'fitting-session' before your Mom comes over this Saturday afternoon" Veronica answered paying little heed to my feelings or plight while only adding to this misery, telling me my Mom was coming to visit on what appeared to be a date they had already arranged...

"Oh God... This Saturday? It sounds like you guys have this all worked out already, how long have you been planning this?" I asked in more of a demand but Veronica, she passed me off saying it wasn't really like that, yet still I wasn't convinced, however by this point, I also knew that there wasn't much I could do...

"We haven't had this planned very long, your Mom surprised me with the outfit, but please baby, don't worry so much" Veronica went on again, telling me not to worry, reassuring me that my Mom wasn't being mean about any of this, or that she wasn't trying to humiliate me...

"Remember, she wants to see this side of you, and trust me, she's not going to laugh... I mean really, she's your Mom Dana, and don't forget! She was the one who bought you this outfit... So come on, enough of your worries and questions, get naked like I said, I want to see you dressed in these clothes" Veronica finished, and I wasn't sure if she was either giving me shit or trying to be encouraging what with the way she was speaking, It was kind of hard to tell...

"Oh, alright... But I swear, I must be stupid or something, letting myself fall for this stuff every time" I said back giving in reluctantly and feeling like a chump, falling for more of these tricks and pitfalls I'd been finding all along this new and very different path we'd taken...