In college, (in Florida) during Freshman orientation I met Ally. We had nothing in common except for an instant liking for each other. Something about the other brought out the loving and playful side of us both. We had silly, warm-hearted fun every time we got together, and that was a lot. I was friends with her and her roommate, Laura, and spent time with them almost every day. Ally was tall, slim, and blonde, a bit angelic. Laura was pale with black hair and blue eyes, beautiful really.

Randomness made them roommates but they had good friend chemistry and shared the cultural reality of being good girls from the conservative, Christian south. They were both sheltered, innocent, and upright. They dressed modestly. Whereas I was some sort of oddball from the liberal agnostic dimension with a good bit of sex and drugs in my experience bank. I was a shameless male slut and good at getting into sexual situations. In fact, by this age, I had managed to be kind of a shallow manipulative asshole sexually multiple times. This isn’t ugly bragging at all, just truthtelling. Here’s the odd thing, attracted as I was to both Ally and Laura, I just loved them innocently and couldn’t have MADE myself seduce either of them. I understood half-consciously that that part of me wasn’t good for people. Spontaneously, I wanted to be good for both of them.

This doesn’t mean we were prim and distant. I’d visit and I’d talk all kinds of silly crap that made them laugh, then maybe they’d make us tea and we’d eat oranges together. Soon this would devolve into orange peel wars and finally into grunting and groaning wrestling matches across every surface in the dorm room but the ceiling.

Yes, of course, there’s sexual energy there, lots of it: Full body contact and heavy breathing and straining muscles and faces inches apart. It was fucking lovely and earthy and joyful and …innocent. It wasn’t for something else, it wasn’t to get somewhere else. It wasn’t about groping or getting away with something. I stayed perfectly within their comfort zones because I loved seeing them happy. We were friends, but not just friends, we were crazy, wrestling friends. Not to puff up my importance but I had the effect of opening both of them up to talking freely about their thoughts and feelings in ways they clearly found liberating. Meanwhile, they looked at me like something new and wonderful and I’m vain and egocentric enough to just love that.

Outside this little world, I was looking for love with blinders on, getting laid every chance I got, and doing everything about love poorly and for the wrong reasons. Obviously I wasn’t alone in having immature relationships at this age but I notice my SERIOUS efforts at love were fruitless while the one place I loved and cherished spontaneously was a little slice of heaven that I didn’t view as romantic.

That was our world during that school year. The third term finished and college emptied out for the Summer break. Laura went home to work and save money. I no longer had a bedroom at home as Mom had simplified her life and moved into a very small place when I started school. Fortunately, there was no shortage of house sitting opportunities for me because Florida becomes a boiling hellhole in Summer and many academics escape to world travels. Friends of mine left me their lovely, beachfront apartment for a long European trip. I had the place for more than a month. Ally asked if she could join me for a while and I was happy to have her.

Literally across one street and a white sand beach from the Gulf of Mexico, the one-bedroom apartment was a  second-story walkup with a little screened porch entryway. Kitchen, living room, bedroom, and bathroom, as simple as can be, hardwood floor, white walls, little furniture. Big windows opened up three walls and made the place feel at times like a sheltered platform in the sky. It was bright and open yet private. There was no air conditioning and we simply let the salty wind blow straight through. On the hottest day, it was tolerable and you could swim anytime you needed relief. At night you fell asleep to the murmur of waves. It was a tiny Eden in a tourist shithole.

Intimacy was unavoidable. We lived in bathing suits and showered off sand and suntan lotion several times a day. We slept side by side in the big double bed, well on it, as even a sheet trapped too much heat at night. Ally was a virgin, almost unkissed, and had never been naked in front of any man or seen one naked. She tried to sleep in pajamas at first, simplified down to underwear, then finally we simply abandoned hiding from each other. After a short period of OMG transition, we dressed for the grocery store, wore suits to swim, and nothing but skin the rest of the time. She had a lovely, well proportioned slim body, with no exaggerations or lacks.

Our playful loving tone continued unbroken. We teased and played and goofed around. We laughed a lot. In the long heat of the day, we’d recline on the bed, talking about anything and everything. It wasn’t long before the golden salty skin and light musk of each other became the elephant in the room. She found my dick weird and mysterious, but the balls too. My penis mostly sat there looking wrinkled, and harmless but I noticed her watching my balls in concern. I asked her why.

“Why are they moving around?” she finally said. I admitted it was kind of weird but totally standard as they reacted to everything going on in me and around me. She sat up and moved a little closer, watching them shift around. She laughed and I joined in. “You can touch them,” I said.

“Will it hurt you?” She asked.

“Not if you’re gentle”, I replied. She experimentally rested an index finger on one of them and pressed very gently.

“It’s firm but very soft”, she said and touched the other. I told her to cup her hand around them, she did then laughed nervously, “they’re moving around in there” she said in surprise as if it was a magic trick, then, “now they’re sort of snuggling into my hand! Are you sure it doesn’t hurt?”

“No,” I said,” It’s pleasant and kind of comforting. We smiled at each other. My penis began to plump up, bit by bit, thickening, and growing toward my navel. She watched, aghast and amazed, quickly retracting her hand from my balls. “Why…?” she asked, unable to clarify the thought.

“It’s just how it works”, I said, “it felt good and this is how he gets hard.”

“I didn’t mean to do that” She apologized. I reassured her that I was fine, it was just me feeling good. My dick gradually filled and stretched as far as possible, she watched incredulously as it stood up by itself, ready for action. “You can touch it,” I said.

“I don’t think I should”, she said and lay back down on her side. I rolled up on my side and we faced each other wordlessly, just taking in the moment. I scooched across the bed a little closer and she lay her head on my shoulder. Mid-afternoon, the sound of tourists on the beach, the sound of waves. We may have slept a little, the smell of her hair and skin surrounded me sweetly. She said, “Look, he’s small!”

“Yup,” I said,” back to being Clark Kent again”. She laughed louder than that deserved. I saw her hand move and lightly touch him experimentally.

“So different,” she said “he’s soft and floppy”

“Wiggle him around,” I told her “hold him at the base and just wiggle him all around, it won’t hurt me”.

She paused, then did just that, and collapsed into giggles. She literally couldn’t talk for a bit. She did it two more times. Then she closed her hand softly around him and he began growing again.

“He’s getting bigger and warmer!” she said, ” why is he getting warmer?”

“Remember, he’s filling up with blood, he’s closer to room temperature when he’s soft.” Soon I was all the way hard again. She continued to hold him but ever so lightly, her fingertips just pressing a little here and there. “He likes you,” I said.

“I’ll bet he likes a lot of people,” She smiled, “Does this feel good?” She asked.

“It does, and I really like you holding him but he likes really firm pressure,” I said. She barely tightened her grip. I rolled up into a kneeling position on the bed, perpendicular over her reclining body, my cock pointed across her hips. She released her grip.

“No, hold him again,” I said. and she lightly held the middle of him. Almost all the feeling is here in the head, “I said, tracing with my finger” then along the underside, here,” I drew a line with my finger along the bottom from the head to her hand, midsection. “The whole penis is sensitive and likes touch but that’s where the big feelings are.”

She moved her hand to cover the head to the midline and squeezed. It felt good, she saw me smile and said, “so like that?”

“Kind of,” I said but everything is about sliding, rather than just squeezing. Suddenly I did a little kegel squeeze internally and my cock jumped up and down twice as if it had just caught a fish. She let go and screamed just a little. “What was that?” She cried out, clearly meaning What the HELL was that?

“Oh, just a muscle thing, watch,” I said, and I did it over and over again. Boing, boing, boing, boing, boing.

“This is weirder than I thought,” she said, more to herself than me.

We ate and swam and showered and found ourselves back in bed.

“I want to touch you,” I said. She looked at me very seriously, but with an expectant, open expression. She was lying on her back holding herself up on her elbows, legs stretched out, slightly apart. I gently touched her face and her lips and traced the line of her jaw down the side of her neck. I explored her shoulders and arms as if I was blind and needed to learn my way around her. I traced around her breasts, just feeling the firm outline. Down across her stomach and hips, I followed her legs to ankles and feet. Not pushing any boundaries, just learning her body. On my way back up I stopped at her breasts and studied them with my hands, firmly and lightly. I squeezed and caressed them, I traced out to the end of her nipples, lightly then with the gentlest pinches.

She sighed, with a little shudder. I kissed her neck and breasts lovingly. I kissed her down to her tummy. She was silent, her eyes closed. I lay beside her and I held her tightly, my front along her side, my cock pressed into the warmth of her hip.

I said, “I’m going to touch you, I’m going to be very gentle.” She didn’t answer.

My hand played along her stomach and thighs, to her breasts and back, in no hurry. When I finally lightly touched her pussy, my fingers drifting gently along her lips and feeling the light softening and the trace of slippery slickness, I said “Is that ok?”

“That hurts,” She said.

“It hurts?” I asked, confused, still touching her ever so lightly. “Really?”

“Yes, it hurts,” said Ally.

I let go and pulled her into a big hug before pulling back to look her in the eyes. “I’m sorry,” I said, “it’s definitely not supposed to hurt. Let’s do something else.”

That moment pulled me up short. No part of me believed that I was causing her pain with my finger resting on her lips but that was a transparent message of feeling unsafe, and unready. There was an inevitable direction to those minutes before she told me she hurt. I knew where we’d been going without really thinking about it, or taking responsibility for it; I’d been on sexual autopilot.

The problem wasn’t about being in sexual territory with Ally, we’d had a blissful, exciting time an hour or two before, being intimate and playful. The problem was trying to move our experience toward a hasty conclusion, toward standard sexual release. I’m not saying this to describe myself as a lovely enlightened person ahead of his time. There were women I wasn’t so sensitive to, women I had hurried along. I loved Ally more than I realized, her pain and happiness were real to me, they carried weight. I could have my friend in an idyllic sexual continuum as long as I focused on her being happy and safe. So that’s what happened.

We spent a magical month together naked, loving, playful, and living in the moment. We watched 30 cinematic sunsets, often while floating in the waves, we played cards at the kitchen table, cooked meals, and took turns hiding each other’s underwear in weird places (apparently I won because a friend reported finding a pair of panties in the freezer months later). We swam, showered, and slept together, we talked about everything including sex, and having less experience, she had a lot of questions.

I often got to use our bodies as visual aids in explaining things.

Ally: (lying beside me in the deep shadows) “Isn’t it uncomfortable for a woman with a man just lying on top of her? It seems like she couldn’t breathe.”

Hugh: “Open your legs.” (Climbs aboard in standard missionary.) “See, if I keep most of my weight on my elbows but also keep tension in my knees I’m never just lying on you. I can hold you really tight like this, and move my hips like this, without crushing you.”

Ally: “Oh, OK, makes sense.”

Hugh: “And you should move too, you aren’t a U.N. Observer.”

Ally: “How should I move?”

Hugh: “However you want, like roll your butt up toward me, toward the ceiling, like you’re getting it as close to me as you can, now roll it back past neutral like you’re pulling it away. Repeat that a few times so you feel it. “

Ally: (Rolling hips) “Do I have to coordinate my motion with yours?”

Hugh: “That happens but don’t overthink it, if you’re up in your head you’re in the wrong place.”

Ally: “Ok, now you’re in the wrong place, or nearly.”

Hugh: (Rolling off, smiling, thing pointing to the sky.) OK.

Ally: “Pretty happy with yourself, aren’t you…?”

Hugh: Yes, thank you.

I probably got a couple of dozen erections a day ( I was 19). Sometimes she would pretend disbelief: “Again?” and I’d do something dumb like hanging a pair of her panties or a hand towel over it, waggle it around…or pretend it was apologizing to her, or pretend it was a phone call “It’s for you” (once she held it against her ear and said “No. Sorry, wrong number.”)

Meantime though, she relaxed and didn’t blink at bumping into it in the shower or in bed, or waking up first to find me “standing for the queen”, sometimes she’d give him an affectionate squeeze. Sometimes I’d squeeze her tits the same way.


We were friends, but not just friends, we were crazy love friends.

We even kept up our wrestling. You would have thought you were watching rough sex, a cock and a pussy poised, swaying, an inch apart but no, it was a struggle for a win and a shot at the championship title. If anything, I internalized the “Don’t fuck Ally” rule more than I should have. I knew if we became boyfriend and girlfriend that our friendship was doomed. I’d do something stupid or disappointing that would change her mind about me. Or she’d want me to be something I couldn’t be, like a man with a long term plan and sensible goals. I’ve often turned away from beautiful things I don’t think I’m good enough to have.

I realized over the very longterm that she’d loved me too and wanted me, even with all my strangeness but that I’d refused her. We stayed friends, even meeting a couple of times after years of separation, but both married or committed. I knew she loved our intimacy and play but I never heard “I’m ready, I want you” and when the habit of holding back is established, it’s hard to break.

Here’s the night I later realized that I refused her.

The end of that same Summer. We’d moved to another house-sit, near Tampa Bay this time, a really sweet little dark wooden cabin in the very un-Floridian shade of dense pine trees in the yard. Big thunderstorms come almost daily in Florida Summertime. The day works toward them through the grindingly hot hours, slowly building massive cloud towers before dramatically smashing them into drops. A huge storm blew in and thundered and poured till after dark when it blasted a transformer and turned off all the lights. Ally and I scrounged up candles and matches and made things cozy and welcoming. We were naked, as we preferred, and started a wrestling match on our bed. She shone gold in the candlelight as we grimaced and grunted, our muscles straining against each other. She was talking smack about me and I was giving it back, trying to pin her. Suddenly she was quiet and just looking up at me. My cock was about halfway inside her. I wanted to slide deeper in so bad but I yanked out saying “I’m sorry, I’m sorry, I’m sorry, that was an accident, God I’m sorry, I almost went all the way in you!”

I heard her say “Oh No!” but in my hot shame, I didn’t hear the sarcasm, the “Oh yeah that would be awful if the man I love fucked me for the first time by candlelight during a thunderstorm.” She wasn’t free enough of her upbringing to say “Put that thing back inside me right now, idiot”. She could only accept the idea that I must not want her enough to try harder than that. We’d reached “READY” but I wasn’t.

So many years later, playing back the tape in my head and hearing her correctly I wanted to shout after my missed opportunity to come back.

I still do.

 

 

© Copyright Hugh Miller 2020

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