He knew all along…

Widowed for the past 5 years or so I now found myself desiring companionship and dating at 55 years old was so crazy! Online sites had become the way forward and I suppose it worked, I was able to at the minimum rule out some bad actors in the process.

Meet Jack…

A few dates, my first stock car race and an overnight fishing trip off the coast had rejuvenated this old soul big time! A hunk, smart, so humble and to boot and always very complimentary. I was still volunteering for city event planning, something I loved doing, now getting back out, trying to cherish the 30 years with my ex, his passing several years prior was so devastating to me… Now I need to get back up, dust off my shoes and try to be productive , especially for my kids, grands and simply just trying to be happy right? Jack and I sat in our lawn chairs late one evening listening to a local band on the square, glass of wine and during our “snuggling” Jack asked if I had always worn my hair shorter?

“OK – what’s your definition of short if I may ask” I said, waiting for him to really put his foot in his mouth…

“Short, like the way it is now, it’s stunning, looks great, just wondered if you’ve had it for a short while or??” Jack said rather taken back as if he had said something wrong.

“Short? Oh my, this really isn’t short, years ago I was much shorter and wore it like that for years. You would absolutely shit if you would had seen it years ago. I loved it and always got tons of compliments from ladies, but getting back into the dating world posed a few challenges. I swear most guys are such dicks or are so pre programmed to women with long hair, it’s deflating at times. I just think I look better when my hair is shorter And I know it’s much easier to deal with everyday. You did answer my wink a few weeks back, it must not be that bad right?

“Oh god no” Jack said as he poured us both another long glass. As a matter of fact, I prefer shorter hair, I really love the super short cuts on some women, kinda’ need the face for it, and there’s one thing for sure, you do have the face to go short! You should try it a bit shorter for sure…

Was it time to speak up now? Was it time to tell this guy that I really love my hair short, like barbershop short, and have forever? That it somehow was a sexual turn on x 1000 % to have a guy appreciate me, my hair and really embrace my total look? My short hair fetish and desire of all things “haircut” at times was out of control.

A bit shorter? I hoped he didn’t just bite off more than he could chew here, and after a few more drinks, it was settled. I made an appointment for the next day, had my hair cut way shorter, and he absolutely loved it. It was like the compliments just would not stop! Finally over the next month or so, I was mega short, as I was years ago, feeling hotter than ever, new guy in my life, everything was so right. Jack so sweet and complimentary, even when I said jokingly at times “wait till next time, I’ll be bald”

Our relationship grew and as it did, our intimacy went to another level. The way this man held me made me feel 20 again, and the sex was rather crazy.  As I look back to this night where I thought I had let the cat out of the bag, a rather tipsy mouth led to diarrhea of the mouth! As always Jack would rub my nape, which drove me bat shit crazy and tonight as he slowly caressed me from behind, the wine took over…

“Feel good babe” as he wrapped his arms tight and pressed his member in my back,

“My god yes babe, I love it when you massage my neck, puts me in a trance” I said loving every minute of it. “Do you like rubbing my neck babe” now pressing my back hard into his Cock.

“Yea babe, feels like I’m rubbing some guys neck, your little boy haircut is somewhat sexy. Why don’t you get up here and ride this…

I freaking melted and was wet as a water hose the more he spoke and rubbed my nape. I had indeed found a guy, the guy, the one who at least on the surface, really loved me super short.

For years I’ve been addicted to shorter cuts, barber shops where of all things, old dudes were in chairs getting scalped, and somehow I loved being right in the mix. The smell, the clippers, the shop talk, everything was such a turn on for me.

My inspection later of my most recent cut revealed a faded out bald pixie, a cut I’ve seen many men have, women not so much. The hairline in back was super high, a tapered bald fade, ears exposed, the shortest I’d been, well, maybe ever! I did go super short years ago (faux fade) which my ex-husband despised. Was this too short? Did I look weird with such a short cut? I was certainly apprehensive, and to be truthful, though I loved a shorter cut, this may have been a bit much.

Again Jack approached from behind and with a gentle whisper seemed to put my emotions at ease…

“Baby you are short, but my god, it’s so damn sexy! Jack said and by now, I was tipsy and my thoughts were of how he held me in bed, working his rock hard member inside me – holding and rubbing my nape area in a firm, but oh so sexy way… I swear having him come in from behind, pulling what little hair I had on top, rubbing my bald nape with the other is something all women should try. It’s like the more I talked about my short hair, the deeper he would go, – often felt as if his cock was in my chest. Hard – but oh so gentle.

I soon learned he loved playing this game, and I went right along and loved every minute of it! See, we both realized fate had put us together. He eventually admitted he had seen my FB page from the city site years back, when my hair was mega short. So he decided to pounce when he saw my online profile on a dating site. Freaking stalker!!!

As I type this, tomorrow will be our 1 year anniversary of dating, a year full of travel, laughs, new adventures and of course – ALL THINGS HAIR! Regardless of where we are, he always manages to find a local barber to “clean me up” as he says. I’m literally in a trance every time I’m in the chair, peering over at him as the barber drops my head. As if my addiction to short hair, barbershops and clippers weren’t enough already, he added fuel to the fire with comments that drove me bat shit crazy. One night after a nice bottle of wine we were “spooning” in bed, I could feel his cock rest against my ass as we watched a netflix flick. Not hard, just limp like rubber snake, right…  I knew exactly how to “get a rise” out of him and oh my did it ever. He was rubbing my nape and predictably he whispered that he needed to clean me up back here, slowly massaging my neck. Then out of no where came the “It’s hard to get hard when I think I’m fucking a dude. What’s up with this short ass hair?” he said laughing as he is pulling the tiny hairs on my neck.

My respnse. Tough shit asshole, I’ll be at the barbers at 8 tomorrow, I’m getting this shit clippered so tight, fucking balded out, don’t give a shit that you don’t like it” I said, now feeling the limp slinky start to stiffen up.

“Maybe a tight Flattop would be nice, bet you’ll be the talk of the town being seen with a woman with a fucking high-n-tight” now beginning to feel his cock pressing closer to my vagina, rock fucking hard.

“And by the way, I ordered a new set of clippers, the big Osters, they’ll be here tomorrow as well. You’ll keep me cleaned fucker or I’ll find a guy who can” I said and by now his erect member was well inside me. That night I took a pounding in every orifice on my body. Pussy, Mouth, Anus – he rotated between the three with reckless abandon. I desperately tried to keep up and step up my game, but this was a thrashing! Now I know his trigger, but now I’m careful not to push to far. Geez, I remember barley being able to walk the next morning.

So tomorrow is a treat for us both. A visit to a super high end salon in town, watching me sit for a skin tight buzz cut, in a packed salon of clients! No barbershop, but a salon packed with ladies all getting their long locks trimmed, colored, pampered – the whole salon experience! For me – not so much… He loves seeing me get sheared as other ladies, all of course with longer styles, look on in shock. I love it! They’ll never know the feeling of hot cum being gently massaged on my close cropped nape. I close my eyes, melt down below, and know what they don’t know – I have finally found my man!