The ruminations of ruminating pt 1 in Musings

I am such an over thinker. I always think about something and then I overthink about it. I dissect it and once I dissect it I dissect the dissections.

Why is he so gentle and at the same time so machista with me as we develop this strange sexual activity? Am I engaged to a misogynist? Does he think women are meant to cater to him? Or is it because I’m a guy dressed up as a woman that he thinks of me as less?

I’ve seen the way that he treats actual cis-gendered women… and he does tend to treat them a lot more delicately, but also there are micro-aggressions… I mean I know, or at least I hope, that these are sub-conscious culturally ingrained customs that he has as a Puerto Rican man.

As a social experiment, and also out of curiosity, being aroused by what makes my own Perception of my own masculinity threatened, I have been crossdressing. I know that it’s arousing to him, as far as I can understand or perceive it arouses him because it’s a form of submission that he doesn’t fully experience of me when I am in my guy form.

Early on during quarantine we both realized that we are two very, very strong-hard-headed men. We adore being with each other, but we also need to have our own agendas for the day, we can schedule one or two things to do together, but I get very frustrated and because I am a spoiled little brat he always appeases me, but that creates an animosity in him and I get irritated at him because he’s not being strong enough to just put his foot down and he does what I want because it avoids a confrontation… and we eventually lash out at each other and we say awful things to each other that we really don’t mean. If you put two alphas and try to force them to co-exist with each other eventually it will be a blood bath. To date, I know for sure that I have never dated a guy that truly, inherently feels and knows that circumvents my dominating personality and actually is competing and sometimes even superseding my own hierarchy within the relationship.
With my prior relationships the guy would drop his money off in our joint savings account and I was always in charge of balancing a check book, deciding what the spending limit is for the week or the month. Alexander made so much more money than I did and his net worth far exceeded my own, but he didn’t care and he would just drop his paycheck into our joint savings account and he’d drop money into my personal savings account and if I said “well we’ve spent $450 last month on frivolous shit, because you have 3 Starbucks coffees a day, you’re taking too many ubers to work, you get your shoes shined 3 times a week, you have a monthly metrocard that you hardly use, we need to cut some of these expenses” Alex would be like “oh shit sorry babe what’s the budget for the month or for the week?” And I’d tell him “let’s aim to cut that expense by 50% and a quarter of that would entail, using your monthly $120 metrocard, we can buy Starbucks coffee grounds and you can have your first coffee of the day homemade, you don’t need to shine your shoes this often, we have shoe polish and buffing whatever that you bought so maybe get your shoes shined 1x a week, doing all of that would cut this over expenditure from $450 to $200 and those extra $250 a month we put in a savings account” and Alex would just fall in line with that.
With Liam, we have a joint bank account that he deposits 50% of his paycheck into, 30% into his personal savings account and he divides the 20% left over for his expenses, maybe he wants a pair of sneakers or some limited edition fitted cap, but it’s money that I don’t know what he does with. Honestly, it’s a huge turn on that he’s so self-sufficient and he’s a man. If he made $3200 from his work (this is his own commission that he makes that is separate from what he invests into his company) he separates that 50% he’s left with into 30% into his savings and then divides that 20% into personal play money (maybe a new pair of Jordan’s, or a new fitted cap or a video game, or taking me out for a nice dinner or at this point buying me women’s lingerie) and the rest goes to weekly work expenses. I don’t know why that makes me pre-cum; thinking that although, I might of been concerned about the amount of money he spent on this little crossdressing fetish we have going, he’s not concerned one bit about spending 1-2-3k on buying exorbitant, expensive gifts that he’s just going to stain with his cum. He’s similar to me in that sense that I don’t like Liam to interfere on my spending habits, and I’ll let something out at this point, because I’m drunk and stoned just ruminating… for his birthday during quarantine he had a conniption because he’s not aware of the money that I have, what my personal savings account has, just like I don’t know his and for his birthday I wanted it to be special for him… and we were going to go to Bali for his birthday but because of covid all of that had to be cancelled, it was his 35th birthday…and so instead of going to Bali—and because Covid even fucked up having me invite friends and make it special—I always believe that a man, like a real, grown ass man should have 3 essential things regardless of there socio-economic background… and this is something my mother has always taught me from birth and it’s an important custom of being a Puerto Rican man—a man should have a wallet, a wristwatch and a cologne; these things are very personal and essential to a man. I don’t care if your dirt poor and you have a plastic watch for 3$, a 10$ wallet and you wear old spice cologne.... I judge a man not by the brand or the price of any of these things—I judge them because of the lack of any of these 3 things… and for his birthday I splurged and it’s his 35th birthday, he’s a business owner, he’s not rich, but he’s not broke and also I was tired of his silly little metal digital Casio watch that he’s had since he was 30… you’re dating ME out of all the gay guys in the city, I’m not about to be engaged with a 35 year old man with a $30 watch when I’m wearing diamonds and thousand dollar shoes—I bought him a beautiful Oystersteel, white gold Rolex…

The way that I was with him for buying me this expensive Ass lingerie… I mean I’m not gonna wear that outside… and it’s literally going to just have his cum stains on it, he flipped his lid about this watch… and just like he was with me when I was like “we’re in fucking quarantine! What the Fuck are you doing buying me this shit?!” And he was like “it’s not coming out of OUR money, mind your business about how I spend my money” I was with him… “you’re welcome Liam… you’re not a child, that Casio watch you love so much is cheesy and you’re a grown ass man, you need to have grown ass man accessories, it’s not coming out of OUR money, don’t worry about how I spend MY fucking money”

Needless to say he doesn’t take that watch off for any fucking reason whatsoever… I didn’t measure his wrist correctly to take some of the links off of it, And I needed to get it resized—because there is nothing trashier to me that a man with an ill fitted suit and an ill fitted watch… he didn’t want to take it off to send it out and we had to drive to the boondocks of nowhere to a Rolex licensed jewelrer and he only took it off when we got there. He showers with the watch, he sleeps with the watch (and I’ve told him he can’t do that, because I’ve been woken up a few nights when he just stretches his arm underneath me and he literally punches me in the jaw with the face of the watch and I’ve also woken up with scratches from it on my neck or my back). I honestly think it’s so sexy the sound of the watch in his wrist. I don’t wear a watch, I don’t like watches and in lieu of a watch I have love bracelets, so I’m always asking him for the time and I find it sexy when I’m like “babe what time is it?” And he just flicks his left wrist and looks at it and he’s just like “it’s a quarter past 8”… I will admit this because who cares? I have ALWAYS been bad at telling time on an analog watch, I don’t fucking know what “half past something, or quarter past something or a quarter to whatever or whatever other analog speak there is” I’ve had to force myself to actually learn time this way… cause before with his digital watch, he would always be like “oh it’s 12:43” which means it’s a quarter to 1… right? Eeep! I’m trying!! I’m not sure if that’s correct! Don’t burn me at the stake! And he’s very unaware about the fact that I don’t know these terms—I’ve just been doing elementary school lessons behind his back on analog watch speak… and also if he tells me it’s “half past 12” I just have to look at a digital watch and see “oh it’s 12:29; half past, half of 60 is 30”

Well enough of that rant… he looks fucking sexy as fuck, in his watch… He could be stark naked, and he just flicks his wrist… and all the knowledge he knows about how to wear a watch, what wrist a man should wear his watch… when I was younger and did wear a watch, because like I said my mother has always, ALWAYS, drilled into my head as a wee little boy, in order to be a man, to be a man of worth (atleast in Puerto Rican culture) a man HAS TO have 3 essential things: a watch, a wallet and cologne. But my mom never told me what pocket my wallet should be in, or what wrist you should wear your watch… According to Liam—and I never ever realized this about him, but I realized it soon enough with the watch… a right-handed man keeps his wallet and wears his watch on his left. And then he shocked me with this knowledge… all of men’s clothing the “hole” is on the left side of men’s clothes, so you wouldn’t see a pocket on a suit for handkerchiefs on the right side of the breast. You can see it on women’s clothing, but not on men’s clothing… yeah… my mind was blown… women can have it on both sides, but not men’s.
Liam puts all of his things on the left hand side… his wallet, his watch, His phone.

Anyway… because I’m drinking and it’s a quarter past 3… I want to keep writing and go into this weird crossdressing thing and my social experiment and also testing my own boundaries of masculinity and trying to understand what it makes me feel—is it something that I enjoy because he enjoys? Is it something that I enjoy because it’s unleashed some sort of inner anomaly that I’ve suppressed? Why does it feel good and feel bad at the same time?

So for the past few days, he always wakes up at the crack of dawn to walk Warby and I wake up like 15-20 mins later… he hasn’t asked me or has made any sort of signaling that he wants to have sex for the past few days… and I’ve taken it upon myself to initiate sex by dressing up.

He walks Warby. He comes home, gives Warby a treat, I’m all disheveled in the kitchen, making him coffee and drinking my own coffee, he drinks it… and he’s like “come run with me babe, I don’t like you being in the house all day, I know it makes you depressed, it makes you feel bad yadi-yadi-yadi “. 1st day… I went running with him, but I’m not as physically fit as he is, I can run 3 miles max and I’m just like “cool, imma run back home, this is my limit, have a good jog” and he continues running for about 8-10 miles.

I get home… I make him some breakfast… and my mind went into a whirlwind of things… first I was like “I’m horny, I want to suck the sweat off his balls when he gets home as he eats his gluten-free, organic strawberry pancakes” and then after that masculine part of me and my overthinking “feminine side” of me overtook I was like “well, I want to have sex, he hasn’t really signaled or initiated, so maybe I will—” I track him on my phone and I see that he’s a 30 minute jog away from our house, and that means I have about an hour and 15 minutes…
I take a shower, shave, lotion—and I begin to put on the costume… he’s not asked for me to do so, and I’m just applying beard cover, staring at myself in the mirror like “is this a bad idea? Is he going to think that I’m transgender? Is he going to see me ass dressed up and reject me like ‘babe this is weird, I hope you don’t think I really want to date a woman’” and my mind keeps spinning…

I have Moisturized, I have primer, I have my color correcting beard cover, I have concealed, I have put on translucent setting powder, I have applied foundation—I track him again and he’s just jogging 15 minutes further, so that means it’s going to be a 90 minute round trip…

I start adding concealer… I start adding contouring on my face to make my face appear more feminine. I catch a glimpse of myself in the mirror and realize for a split second what I am actually doing? … “Andy?! Is this something you enjoy? Is this something you enjoy because you like pleasing him or is it because you, yourself intrinsically find the experience pleasurable? Do you need to have an honest conversation with yourself about your gender identity or is it that you’re just a twisted little fucker that you just get off on making yourself uncomfortable and just playing through the Kinsey scale of sexuality like a xylophone?” There goes the blush and my face looks really feminine with the help of highlighting and contouring and creating illusions.
I put on blush… Warby is sitting in the bathroom and his little head switches from side to side like when I was a little boy watching my sister and mother transform from beautiful women, to sexually desirable women… curling my eyelashes. Filling in my eyebrows. Putting on false eyelashes.

I will tell everyone right now… male, female whatever—I am super artistic, my mother was a textile designer, my family is all very artsy and I grew up knowing how to draw—HOWEVER, it is motherfucking WITCHCRAFT to successfully use a liquid eyeliner and draw wings or cateye liner.

I look at the tracker again… Liam is running back he should get to the apartment in 45-50 mins; I get a text message from our joint bank account saying that he swiped $3.00 at some “Adam’s Deli Corp”
I’m drawing in my lips… for some reason or at least from my surveillance, Liam is really, REALLY, wildly into the color of this Fenty Lipstick “mattemoiselle” it’s like a dark burnt sienna color and it makes a really rich dark berry, orange color with the lipliner I pair it with—it’s very super gothic… and it’s matte… but I also use a dark berry lip gloss over it…

I’m not going to lie and say that I don’t spend a lot of time admiring myself in the mirror when I’m all transformed… I look like my sister when she was younger, who was/is a super stunning woman… but she was scary and intimidating, because she was never a girly girl, she was/is a goth chick… side note: I showed my sister pictures of myself in this costume and she looked at it and was like “wait, I’m confused who’s this girl—I don’t remember ever having blonde hai—wait?! Is this you?!? Holy fucking shit!!! First of all, you look like a fucking hotter version of me and SECONDLY, are you transgender? I’ll support you if you are” and she snatches the phone away from me and scrolls to see more pictures of me “HOLY MOTHERFUCKING SHIT BABY BRO!!! You’re like a fucking HOT girl AND you’re a fucking hot guy!!” And I told her “I’m not transgender, I like being a guy, this is just experimenting with things” and her reply was “OH MY GOD! I’m the only genetically born girl in this family and you seriously—holy shit I’m just; like—it doesn’t shock me that you’re dressed up as female, it fucking shocks me that you are a handsome guy and you’re a hot girl… like I didn’t even know you had thighs like that!!! “

I look at the tracker… he’s about 15-20 mins away… I scurry into the bedroom and pull out that box of the lingerie that he’s bought me… I settle for these lace Gucci pantyhose, and this weird Agent Provacateur black lace, studded contraption—and as I’m putting on the underwear and ripping off the tags I’m just thinking like “omfg, why did this man spend this much money on woman’s lingerie for a dude?! Like is it because he knew that I wouldn’t wear something cheap and trashy? Is it because he thinks of me as a woman and he wants to push me toward that?”

There’s something really sensual that I understand now that women feel, when they slip on those lace contraptions and feel the silk against there skin and feel a slight sexual arousal and absolute power when they slide on that g-string and place that string between your ass.

I check his location again and I see that he’s stopped at the corner and as I throw my phone on the bed… he FaceTimed me… I rejected the call and then I just called him regularly, as I’m slipping on my wig, simultaneously sliding my foot into the Louboutins stilettos.
“What are you doing babe?” He said as he sounds slightly out of breath....
“Not doing anything, just finished making you some breakfast Li” I said feeling my voice quivering… “why?”
“Oh aight… you been stalking me? You sound outta breath… you got someone at the house?”
“Oh my god! No” I yelped.
“Yeah you sound weird babe....” he paused. “Well you can see I’m like a block away from the house… babe, I’m telling you right now, that tracking me makes me feel a little suspicious, I feel like you’ve been acting a little weird for the past few days—if you’re cheating on me, I swear to God Andy that nigga better make sure I don’t see him in the lobby—I will break his fucking jaw and when I get upstairs, with all my fucking heart I’m taking all of your shit and throwing it in the hallway, you feel me?” He said
“LIAM!” I screamed as I stood up and wobbled in the heels “you really think I’m that gross and cheap to fucking cheat on you?! You fucking asshole” I screamed.
“Aight. I’m just letting you know babe… I just feel it a little suspect that you checked my location like 7 times and you ran back home, you’ve been acting weird and I’m not in the best of moods today” he said. I heard him get into our building and the doorman greeting Liam.
And it kind of pissed me off that Liam asked the doorman “Did you see Andrés go upstairs today? Any visitors?” And I literally yelled hard… and the doorman said “No sir, Mr. Andrés came sweaty and tired and as far as I am aware there haven’t been any visitors”
“Oh okay” Liam said and he’s hearing me yelling on the phone… I am LIVID.
“You know what Liam, fuck you. You asshole” and I hung up…
I grabbed the black duster from the living room, pulled my wig hair out of the back, sat on the kitchen barstool, put Warby on my lap, and I was FUMING.
I hear the jingling of his keys in the door, and I just yell “oh my god! Nick just hide under the bed my boyfriend is here!!!” and he burst in through the door…saw me, In all of my fucking crossdressed glory, as Warby was whining in my arms because he wanted to greet his father.

He pulled out the keys from the door, and he turned beet red. Closed the door quickly… I’m tapping my foot… I put Warby down on the ground and at this point Warby is confused and I literally walk away to the bathroom and Warby follows me…
“Babe!!” Liam growled and ran behind me and grabbed my hand before I got into the second bathroom. “Fuck! I’m a douche!”
I turned around and looked at him, like really bro? That’s what you think of me? Like should I think that you’re cheating on me when you check my location 4-5-6 times in an hour?
“No! Babe” and he just dropped down to his knees, super Puerto Rican man dramatic When he knows he really fucked up and pushed his head on my stomach “Babe, I just feel like you’ve been so strange the past few days and it bothers me that you’re so in your head and I don’t know what you’re thinking, but I like that I don’t know and you just make me crazy, I’m sorry!” And he pressed his head into me. “Baby I’m sorry, you look so fucking beautiful and I’m just stupid, I know it takes a long time to get like this for me” and I mean, I can’t blame him—if I was engaged to me, I would go equally as crazy, because I don’t really say a lot of things out loud and I do act a little separate when I go into my rumination mode.
I caress his face and hold his hands and pull him up… and his hands grazed from my ankles, up my calves, sliding up behind my thighs, up my ass and ending up holding my waist. He’s 6‘2 and in these fucking stilettos I go from 5‘8 to 6‘1.
“Holy fuck Andy—“he said pulling me into him as he slid my duster down my, dropping it to the floor and putting his hand behind my neck and caressing my jaw with his thumb “I’m such a fucking lucky ass man, to end up with a girl like you, a boy like you, a fucking plant like you, a cloud, a king, a Queen; you’re fucking so beautiful and I’m really sorry about everything” he said as he rubbed his thumb over my lips.
“It’s fine babe” I slid my hands under his compression shirt “but let me tell Nick to get out from under the bed” I kissed his hands.
“Too soon babe” he said pulling me against him as he leaned against the kitchen counter “fuck Nick, you think he has a big dick like me?” He laughed in my mouth as he kissed me.

I dunno… I enjoy this costume party, because I feel like I see a different side of him. In my boy form he’s arrogant and cocky, but it’s not as barbaric(I think? Still trying to figure out the adjective to describe his personality when I present as female)

We make out for what seemed like 3 quarters past on an analog watch and we are both ridiculously turned on and like I said earlier “I want to drink the sweat off of Liam’s balls” I legitimately want to pull off his compress underwear, wring them out and drip his sweat in a martini glass, with some Hendrick’s Gin, and a splash of vermouth with a lemon twist—stirred, not shaken. 4 parts Liam sweat, 2 parts Hendricks gin, 1 part vermouth.

“Baby, let me take a shower really quick, I don’t smell nice” he said as he slid down the strap of my lace contraption. “You smell so fucking good and I don’t want you to get dirty with me” he said as he pulled down the cup of the lace bra.
“No… I like you like this” I said kissing his clavicle. “I think you smell and taste amazing” I said pulling off his shirt.
“You like me dirty like this princess?” He said. (Which by the way I feel a lot more comfortable when he refers to me as the gender that I am presenting, and we had this discussion—because he would tell me ‘you’re my boy, you’re my king, you’re my man’ and I’m dressed up as a whole woman and it was weird and awkward because the fantasy is that I’m a girl and not a boy—does that make sense?)
“I love when my husband is dirty” I said as he slipped off his sneakers, kissed me and slipped my hand into his compression underpants.
“Look how hard and horny you make me princess?” He said as he pressed my fingers onto the wet tip of his dick. He dropped his underwear and stepped out of them and sat me down on the kitchen stool as he rubbed himself on me…

And again here’s comes the confusion and my rumination… he moves over the g-string, wraps my legs around him, rubs his tip on my entrance and carries me to the bedroom and he says “you know that little hole belongs to me?” He says as he kisses me deeply, he’s not lubricated and it hurts… and here is the weird thing, well not weird, just confusing for me and my own masculine identity “You know your Papi is going to teach you how to be a good girl, and a good wife” and in my head… I’m just like—I’m not ever going to be a girl and I will never be a wife—I am a male and I don’t think that his idea of “wife” or womanhood, no matter what level of womanity you are in…a cisgendered woman, a transgender woman, a male-presenting Lesbian, is ANYTHING that I want to be. But then again!!!! Why the fuck does it turn me on?!? Do I get off on being emasculated??!!

As I am laying underneath him and he is stark naked, except for my birthday watch he wears everyday all the time, he uses a shit ton of lube and he fucks me—but it’s not like the way he would when I’m a gay boy… as a gay boy he fucks me but he’s considerate, he talks to me, he connects with me, he doesn’t have this strange authorization, from God knows where. He has this mentality that I belong to him—but not the way that I deserve; it’s like he’s already made the story and I’m just a character in it and I’m not a person to him…but obviously he’s my fiancé so it’s not like he’s a rando that says that, it’s like we exist in this borderland.

As he fucked me missionary, he’s kissing me deeply and I’m just whimpering in his mouth… and it amps him up. I want to slip off my shoes, mostly because they are expensive as fuck, I want to slip off of the lingerie, because I know for a fact that he doesn’t cum inside of me as a girl… and it’s really weird, interesting nuances like that… I mean I should have a more in depth conversation with him and what certain things mean for him… So he doesn’t pull out of me when I’m presenting as male because it’s part of that fantasy, right? Men can’t get pregnant.... but as a crossdresser or as a ‘woman’, he always, always pulls out… I mean I don’t know why?! I’m still a boy underneath the glam and lingerie…I’ve never forthright asked him.... but my week of this social experiment (unbeknownst to him) I’ve realized these little nuances.
Because everything about this entry is TMI… even when I try to hold him in me, when I know he’s about to cum—he always manages to pull out and shoot all over my stomach----which wasn’t something that mattered to him when I’m a boy… but it kind of infuriates him when I’m in this costume. He develops Hulk strength, both physically, because he forces himself to pull out and he holds in his orgasm until he’s completely out of me.... and personally, I think that ejaculating in me completely naked as a boy is fine, and I’d rather either he wear a condom or just cum in me; do you know how difficult cum is to remove from silk?! Just cum in me! So I’m not trying to remove semen from just silk you buy from TJ Maxx at discount from a bargain bin… this is super delicate fine Luxurious silk… I can’t just throw it in the washing machine and how embarrassing is it to not only take lingerie to the dry cleaners as a boy, but to pretend like that semen stain isn’t something you didn’t know about ....to be continued