LITTLE BILLY

Last week I regaled another story of the time I lost my virginity when the clan and I were all telling of our "first time sex" stories over drinks for Pride. Well, here's another one from way back in the mid 90' when I lived in downtown Harrisburg with a housemate. We rented a four-story townhome right in the heart of the downtown. Now I don't know what it is with me and Prides, but something sexual always happens. My first ever gay pride I met two guys, a couple, and that ended up being my first ever threesome. This story was two years later. After the festival, everyone went separate ways home to rest before our big Pride party that evening. Not being a big napper then, and being newly living in the downtown, I thought I'd go have a few drinks and see what trouble I could find. It was hot, and sultry that day and I went on the prowl. So I go to a place called the Strawberry Lounge and to my delight there are a few possibilities. What do I do? I sit next to the one impossibility. He was super-hot, chiseled everywhere, major jock, killer smile... and looked like a young George Clooney when he was young, like on Facts of Life. But better than that, he reminded me of one of the hot jocks from high school I'd had a crush on, who was also out and slept with the other four out gay boys in school but me!  So anywhore, he looks at me, I'm looking at him...he is pulling up and down on the neck of his Rolling Rock bottle, and I'm rimming my finger around my cocktail glass. Finally, he says," What are you up too?" I says, "Oh you know, just looking for sex." I have always found the direct approach works best. Then he asks me what my wildest fantasy was. I said I didn't really have one. I just like to see where the day or night takes me. I then said, but you must have one, because you asked the question. And he said, Yeah, I do. When I was in grade school, I had a huge crush on my friend little Billy. One day I rushed to his house, and was greeted by his mother, we talked, and she told me to go right on upstairs, he was in his bedroom. But as I went up something felt different that day. I got to the top of the stairs and his door was closed with exception to a slight crack. I opened the door, and there was little Billy, on the bed, Fruit of the Looms and pants down around his ankles, bare butt up, humping a pillow. I said little Billy! He turned in shocked, red, and said well, buddy you caught me. I then started to walk over to the bed."  Well, I interrupt and say I guess you want to reenact this?  And I'm to be little Billy? He says..."Yep are you up for it? He looked down and saw I was. I finally said yes, I'm up for it, and better than that I live in a four-floor townhouse, and my bedroom is on the top floor, so your fantasy is going to be that much more authentic. 

So, I down my gin, give him my address and ask he give me a five-minute head start. I ran home, in, and took two steps at a time. He was going to get little Billy and I was going to get my fantasy of the high school jock. I unmake the bed, putting the humping pillow in place and pull off my shirt and pull down my jeans and Calvins. I start to hump the pillow when I hear the door open and shut, I hear him acting like he's talking to little Billys mother, and says Thanks Miss H, I'll go right up. And I'm thinking to myself, he really knows this script. I then hear him coming step by step up the stairs, he's close, then I hear the door opens and he says Little Billy! I turn in shock and red, but not from embarrassment, but from the running and the gins from earlier...and I say," Hey Buddy you caught me." he says "I sure did!" He then starts to walk toward me, and I can see he's majorly tenting. I reach out and pull down his jeans and his tighty whities and out pops a big, beautiful kielbasa sausage, and I want to say hold the bun, put the ketchup and onions on the side, and just as I lunge for it, he dribbles out, he pulls away, pulls up his tighy whites and jeans and says, "Thanks Buddy! Thats was hot...You did great!" I said "Thats it...THATS IT!" Thats what I wanted to say but was too flabbergasted to say anything. Why not just leave me $100 on the dresser why you're at it. He leaves, I hear him go down the stairs and out the door, while I'm lying there still hard and laying on the humping pillow. Mind you I also didn't hear him say goodbye to little Billy's mother on the way out, which I found rude. And then I'm like, this isn't the first time he's done this. This guy is in a rut.I also wondered how many other little Billy victims were out there. I wanted to go find them and start a support group! And what about me? I didn't even get my high school jock crush fantasy come to life. But....but I didn't tell him that did I?

 I learned a very valuable lesson that day. Never be afraid to ask for exactly what you want, you might just get it. 

Hey, it worked for him.

Mr. TUBESOCKS

What with gay Pride and everything here, it bought about some conversations over the weekend while at World Pride. It was about our coming outs and or first times for sex. What better time to regale another Tale from the Boudoir. First off know the Mistress was never in the closet kids. I was born out, and an early bloomer. I think I was born with a high libido also. Which over the years has gotten me into and out of trouble. 

My first earliest memory was in grade school and later in middle school with some slap and tickle, and a few "explorations" of a few boys at sleep overs. But the real piece de la resistance came from what could have been a huge scandal that would have surely rocked the neighborhood bitches. In middle school I was good friends with this guy named Bill. We were cut from the same cloth. Both pickle kissers. It was where I think we both learned more about the cock and delights from other acts. While we weren't joined at the hip, we were together a lot. But if truth be told, if was his Dad, that really got my attention...to stand at attention if you know what I'm saying. For a few years I thought his dad must know and see my hunger. I meanwhile, I must have looked like Chrissy Metz being held back from a Krispy Kreme joint. I never told my friend, but the real reason I loved going over to his house was because of his hot dad! I'd find any excuse to go over to his house too. When not working, all his dad's time was spent working out. He had big arms, big legs, and a hot body for a dad I thought. Then there was the porn stanche!  In hot months he lived in shorts and tube socks. And it was hot. A few times he caught us on several occasions at night enjoying each other, and then that would kill the mood. It wasn't till high school, and Bill's parents divorced, that things changed. In my sophomore year I recall going over to Bills, I rang the bell and ask if Bill wanted to hang out, only to be told by his father he was at his mother's all week. He asked me to come in anyhow and enjoy the pool. He gave me one of Bills swimsuits and we changed. Need I say more about seeing his dad and I change into swimsuits?  Talk and innuendo ensued with some light touching, but nothing happened till a few weeks later, when Bill was supposed to be out till late. I knew this. But my web was spun girls. I acted as though I was returning something of Bills knowing full well his Dad would invite me in. Sure, is shit, he had on shorts and tube socks. His eyes were looking all over my body, I could tell. This long cat and mouse game was finally going to come to an end. He sensed my stirring and urgings, and there was no hiding my excitement.  It wasn't long till his arms placed me on the sofa. Kissing ensued, hadns were rubbing all over, and our bulges were poking at each other, and then the clothes came off, and let's say the afternoon heat, being naked, and his hot body, and very nice manhood, all conspired to make for an afternoon of enchantment. He was the first man to really kiss me good, not to mention my first time going whole hog...the whole nine yards, things to make my toes curl.... no longer a virgin kids!!! Not to be TMI, but I can still recall that perfect cock. When we finished, we laid on the sofa, where his muscles were flexing in the light, I got hot again, and we ended up masturbating till we climaxed. Before I left, I was stoking his chest and feeling him up again, and I let him force his tongue down my throat before leaving. This happened a dozen times or so over the course of the year, till Bill walked in once, and the jig was up. As you guessed the friendship severed. I mean I had had sex with my friend, and then his father, many years my senior. I saw his father maybe once or twice after the blow up, and I asked him if I could have a picture of him to remember him by since it was best to not continue fucking. Ok, ok Spank Bank material!!!  And yes... I still had it! Hey... come on, I'm sentimental what can I say. The visual aide...

To my knowledge, my mother said he is still in the area. He is now 79 years old. And NO my family never learned of our affair, at least not till the memoirs come out. I mean he was friends with my father. And to this day, it's why whenever I see tube socks it gives me an instant erection and gets hot me!!! I can't even go down the sock aisle!

THE NEW YORK TIMES

 
Another installment from my hotel series who knows, a possible memoir story one day. I just LOVE hotel room assignations and love hotel room service... and not sure if it's because of my experiences or I just love staying in hotels. Both, I guess. When I used to travel with Bloomingdales, I often went to the NYC store for resets and huge moves at the 59th street location, which were always from M-F. I'd go the previous weekend for getting out, taking in the city and any debauchery I'd find before the week would start. The last trip I did with Bloomies was the summer before covid hit. I was at the Renaissance Hotel in Chelsea. So, this visit one morning I order, breakfast room service, two eggs over easy, of course, bacon, toast, oj and a pot of coffee. Oh, and a NY Times. KNOCK KNOCK! "Room Service". I open the door, and standing there with my breakfast tray is a really cute, mid 20ish, tall and skinny guy, adorable! I said, "That was quick, just place it over on the credenza." So, he brings it in and sets it down. The whole time I feel as though there were strong vibes of electric, but I wasn't sure.  He says, "Will that be all?" I said, "I think so." So, he starts to leave, and I happen to notice the newspaper wasn't there. He apologies and said he forgot it. So, he goes to get it. Meanwhile I am waiting for him to return, but this time I'll keep the door ajar when he comes back. He can knock and I'll be clad in my robe by the credenza. Maybe reveal one of the gams I proud of. KNOCK KNOCK! "The door is open." says I. He said, "Here is your newspaper." I said just put it down right there. I give him the eye, he gives me the eye. And back and forth it goes. He then said, "Will there be anything else?" I said "Wellllll, I'd like a little bit more." He said, "I would love to do that, but it's really busy right now, and if I got caught, I could be fired." I said I understand that. He then says, "But you know what, I get off at 2:30." I said "Oh really? Well, I don't have any plans today and work doesn't start till tomorrow, so here is my cell number, I'll be up at the pool." So, I go up to the pool. Four hours later my phone rings, and he says he is coming up through the fire staircase where he won't be seen. So, I run down to the room with my towel and square cut on and get to my room and there he is waiting. And the story has a very happy ending!  He came into my room, the clothes were ripped off, a hot time was had, and I got to have my lovely hotel assignation, AND he kept his job! Not to mention the NYTimes kept coming the whole week. God...I miss my expense account days.

FROM THE CANDY SHOP

A very special treat in the Candy Shop today. Some very tasty Spanish candy, that is as tasty and melt in your mouth goodness as it looks. I had firsthand knowledge with this candy, the adorably sexy Guille Choa... as he is friend with one of our clan members, and I had the pleasure to meet and hang with him for a week, a few years back in Provincetown. But I will never kiss and tell, unless you plan to ply me with a few gins and tonics and hear some sordid conversation. I will admit that that this man took my breath away and left me very weak in the knees, just from his smile and heavy accent and good conversation. We even kept in touch here and there, so a sweet guy and has many talents, I am leaving it there. He has a cross story, started out as a fitness instructor then made his way toa sports nutritionist. But he is also very uninhibited and doesn't shy away from being nude and letting it all hang out, to the point of doing some modeling. I tell you; I can never escape the Latina and Spanish men. Here are some links to check out. I hope he comes for a visit soon!

Twitter. Instagram. Only Fans. His sexy massage!

Ahhhhhhh memories

THROUPLES

 It may surprise some to find out that for a good year and a half I was in a troupe once years back. I can't complain, it was great fun, exciting, and do think its possible to love more than one person at a time. Back then, I didn't really broadcast it, as it was just not understood and as usual, I was ahead of the times, American just wasn't ready to hear the details. And even now some don't get it, but I have found a loophole to explain why it is now acceptable.

THE FLEETS!

Another reason to love the heralding of summer...FLEET WEEK! It's my wish every gay guy could experience Fleet Week just once. I always loved this time of year for many reasons. Just another excuse for a trip to New York City I say. At one time, most of the Clan lived in Hell's Kitchen, the Village and Chealsea, and I always went up several years in a row to partake, and I can't tell you how excited we were to be there to greet and gladly receive all the seaman. It was in a sort our small contribution to thanking them for their service and making them feel rewarded in way. If we could make them happy and enjoy time away, who could resist not commanding their wish? It's truly a site to be seen, with the uniforms all over the city, touring, in bars, and landmarks. In their various uniforms, and their smiling and wanton faces, their randy sides showing... seeking time away, and the look and wonder of the city's offerings. And if you should ever go, they usually set up command center on Pier 88 in Midtown near where the Intrepid is eternally moored. This would be a great place to start, with your tight skinny jeans, tee shirt, and come-hither smile. Every year in the Village bars, the boys like us came out to play. Some years I met some seasmen and had good conversations, and sometimes sex, and other years, one in particular, a navy man and I may have gone the whole enchilada. One navymen one year, was of the first few to give me some enjoyment of one of my first 10". When we were undressing, I was unbuttoning his pants flap and out popped a huge bouncing flounder!!!! I wonder if that is why I prefer a man in the navy over the other two branches??? Regardless of what you do or don't do, it's a swell time, to even just hang and talk, and if sex happens, so be it. I like to think of it as doing my part to boost the morale of our boys!!!! But hurry, the day after Memorial Day they pull up stakes and head back out to sea.

Happy Fleet Week to our Boys!!!!

*pictures 1,3,5,7 courtesy of clan member Preston on our adventures in Fleet weeks.

EASTER TRICKS

 

With the passing of Easter it made me recall an Easter ages ago, back in the mid 90's. I was dating a guy at the time named Richard who just happen to give alcohol up for lent. To be a good sport, I gave up alcohol too, and I was drinking a lot then, so by time Easter arrived, you know I was getting pretty cranky. The night before, we went to see my parents, where we both said we couldn't WAIT for dinner the next day to finally get to enjoy some wine... where my father, the big drinker he was, announces, "Well you know, Lent ends at midnight, so y'all can start drinking after midnight." Of course, my mother was appalled and relied not to encourage us. So, both of us thought, well, were drinking at midnight! So they went to bed, and we headed out and hit several of the gay bars why we were in town. Well... we started throwing them back. The next morning, the phone is ringing. It's my mother. "Are you both up? Hurry up, meet us downstairs, I want to get a good seat at church service. It's Easter you know." Yes we'll be there. I hung up the phone and look over, and there is Richard, snoring logs in his bed, and I'm on other bed, and then there's the guy he picked up in my bed, and the guy I picked up was already gone, and this guy won't shut up. And I'm like yeah ok whatever, we can't really talk, we have to get out of here, and he just kept complaining about his job, his family and Easter in general... I'm just like shut up, while trying to wake up Richard..."hurry up we got to get up and go to service", and he's like no, I'm not going to service, and I'm like yes you have to go, Then the phone rings, it's the mother again... Hurry up, what's taking so long?...I mean, you could see a split screen of me, try to get Richard up, trying to get this chatty Cathy out the door, and then dealing with my Mother and Grandmother on the phone, while trying to get their Easter bonnets on, which my grandmother always wore on Easter. So I hang up and tell Richard he has to get his guy out of the room. He said, He's your guy. I said no, he's not. He got in my bed when my guy left. So, he finally gets the guy to leave, we get ready fast and head downstairs, where my mother isn't happy, my father rolls his eyes, and my grandmother if still fiddling in a mirror with her hat. Well, we finally get to church, it's packed. And hot. No air conditioning. My mother who's getting anxious about setting together, gets the attention of a guy whose says he will give his seat up so they can sit. To my horror it's the other guy who I picked up and he says it's the least he could do for last night and showing him some fun at the Easter egg hunt. My grandmother hears and says that must have been fun? Did you find any she asked, Well, yes, six, I replied.

MR.COFFEE

 

So... I'm at a visual opening on Long Island out by Manhasset in the last century when I was a regional visual manager for a past company I worked for, Coldwater Creek. It was several long tedious, tiring days, and late nights of meeting a deadline getting another store open and immaculately displayed. We stayed at a very swanky Hilton, and every morning for breakfast we all met downstairs in a private room,  and there was one very hot and sexy and flirtatious waiter, gawdeous, tan, smile to melt you, tight bubble butt, Italian and has these very cruisey eyes. Even my boss who was gay said a couple times, "Have you seen one of our waiters? I'm dying to have coffee guy." And I said "Well, I'm pretty sure he could be had, pretty evident he plays for our team, but you know, we're here to work."  So, it's the last day of the store set up, and there at breakfast again was you guessed it...Tall, dark and Italian. he's pouring coffee for everyone, and he started making some serious eye at me. I got the hint. I couldn't take it anymore, and thought to myself, I have got to see if I can make this happen. So, I excuse myself to go to the rest room, and sure enough, there he is,  Mr,Coffee, waiting against the wall in the bathroom feeling his crotch. I said hi and he said "What's you room number? I say 252. He says, "I meet you there." I said I had to get back to breakfast, but  not taking no for an answer, he said just leave. "Well, I don't have much time, I have to eat, and check out and catch up before our corporate van leaves." Insistent he says, "We make time." So, I go back into breakfast, take a bite, and make the excuse I'll meet up with everyone at the van, I have to go up and pack quick as I hadn't done it yet, or so I said. So I go to my room, and there he is..."Ok, I said I very, very little time". He says, "We make it fast." We go in the room, strip from the waist down, were both hard already... and 69ed each other on the bed, fast and furious...so fun...so hot! It didn't take long before we climaxed. What a beautiful man!!! I thanked him, grabbed my bags and run for the bus. Of course, I'm the last one on. My boss was tapping his watch and says "Maddie Baby, we missed you, we were waiting for you. The van almost left without you." "Oh I'm so sorry, I said. "Well what happen" asked my boss. I said, Oh, I just had to grab one last cup of coffee."

I'LL TAKE AN OLD-FASHIONED

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BIG COCKS? FUN?

The other day blogger pal Big had a whole post about big dicks and can they be too big? It got me to excited and thinking about this. Our models for this post for visual aids will be Deigo, Keegan and our own Cali Boi! Big cocks fun? Yes and no.

 Now, I won't lie, I can be a size queen. I have always seemed to luck out, by pure accident mind you, on being a magnet for big dicks. It seems that most men I "meet up" with or have dated just happen to pack a nice piece. I don't know if it's my ass, or I have an invisible tee shirt saying such, but I don't go advertising I'm looking for it. Of course, being highly attracted to South American men doesn't help my defense. I love seeing, playing, giving a handy to a man with a big dick, and even having some oral fun, if you can dislocate your jaw enough, and smear your expense Amanda Lepore lip gloss.

 No... sucking them can be fun. And there is nothing like sleeping naked with a man with a big dick in bed at night and feeling all three legs up against you. But when it comes to anal...Nooooo. Now I have had a few that know and have the sense to know, how to use what they got and take in my needs and comfort level, but others just want to stick it in and jackhammer away! I'm sorry, I'm not one of those gay men with an ass like the holland tunnel, or one that looks like a wreaked-up mess. Since I top more often, I pride myself on being more, as I'm often told, "very tight" back there. I don't think a big cock is always the right size to do such if you're a tight bottom. I can remember this guy named Tony I met years back in my early 20's. It was a bar hook up, and he was so cute. An airline steward. Well, after talking for some time, we went back to his hotel, and when I revealed his cock, I was very perplexed. I know, I must have been looking over it, and over, and bending it around like a doctor during an examine. But I didn't know if I should lick it, pet it or feed it a peanut!! But I knew then I loved the weight and thickness of big ones. He ended up screwing me, but he was a very good lover and caring, but kids, I saw stars for days after!!!!! Every time for years he came to town, we would hook up, but I would end up topping, though I did let him at times top me. I would just sit on a block of ice for the next two days. I wonder what ever came of him? Man was he beautiful.

But are big dick fun and nice to have?

Being told to stop because it hurts too much or you're hitting too deep is not a good confidence booster if you really care for your partner. Honestly, it's wildly uncomfortable and inconvenient UNLESS you're one that likes to have a double wide locomotive ramming up your backside.

While I myself am just above average, I know in some of my favorite undies, if they should shrink, the goods don't fit comfortably anymore...so I can only imagine how uncomfortable it must be when it comes to wearing pants, short shorts, or certain types of underwear. Running shorts, I was told, are hard to wear without getting looks, as the same with sweatpants. And heaven forbid you get an erection. Where is all that going in a confined space? 

And I'm not sure if the weight of such a big dick comes into account. Does it get annoying like the issue that woman have with big boobs? Like Deigo above. I adore his piece, but does the weight of that thing get annoying? I also think porn does not give an acute account on the big dick either. They make it look like a walk in the park. I had another lover that wasn't a good lover and had me go from an ok singer to an opera soprano in minutes!!  The key for me has been finding the right position to please a big lover, 7"8"or even 9" is fine and workable, but anything bigger takes some time and patience, and maybe a bottle of Gun Oil, and for good measure, two very stiff gin and tonics and a favorite shoe to bit on. But it can be done. I have a few friends very hung men who get turned away from sex and they just don't have sex very often for the reason of being big. I used to help one of them out from time to time as we were sexual compatible, when his partner left, and the issue was the sex hurting. So yes, I think big dicks and big dick sex is annoyingly over-rated and honesty, if a hung partner doesn't use care or finding comforting ways to use his can of Monster, or if your partner isn't about size, dead bedroom is ahead for you. Only bonus is that you catch more airtime when you do the helicopter. And don't get me started on double penetrations. That's a whole other story.

That's it for this week kids...I'll be back next week...another weekend in the Pocono's glamping!!! Now go find a big one to research and report your findings!!

MOOD BOARD

Well, not much to report from the weekend, other than another humid one. You know what I do to keep cool in weather like this, I put my undies in the freezer!!!! I got a nice lunch with friends and dinner with others on Saturday Sunday spent in the garden. This week has got me in a mood....the libido is thumping. A good friend of mine and a past , huh, well let's say, a guy I had many picadillo's with, you may recall, the Stock Broker, because he looks like one, is coming for the week from Singapore. He is treating himself for getting his masters degree completed. It's been ages since he was back for a visit, but we have always stayed in touch. A nice slender handsome Asian.... I wonder if he will show me a Singapore sling? And I was tickled to find Bel Gris, a fine specimen of a man of Instagram, and he actually dm'd back!!! He told me to join him on Twitter. Of course, I had to decipher his Spanish!!!! My translator was off that night. But did he get me into a randy mood for sure!!!!! I do believe I'd be putty in his hands, and I adore him for not using labels, as he himself blows the direction of the wind.

I do believe I'm going to pitch the idea of Bel Gris and myself spending a weekend in a Volkswagen bus on the beach....