A word of encouragement

“Take off your clothes,” she said after letting me in. We’d never met, but for the last week we had been discussing plans for today over email.

I did as I was told, as I had agreed to do, and she watched. She watched as I pulled my shirt up over my head, and as I stepped out of my jeans.

“Now the rest,” she said, pointing to my boxers. Something stirred in there as she pointed, but I didn’t begin to harden. I was still a bit nervous for that. Nonetheless, I tossed off my boxers and stood before her completely nude. I watched the way she looked me up and down like I was a statue that brought her pleasure. “Now go sit on the couch.”

She sat across the room from me on a wooden chair, legs crossed, eyebrow cocked. I took the opportunity to look her — my boss for the time being — up and down as well. She was older than me by quite a bit, tall and voluptuous. She wore an airy lavender skirt and a creamy light blouse, unbuttoned enough to give me lovely glimpses of her deep cleavage as she shifted.

“Now,” she said, as if she had to ponder what to say next, as if we hadn’t already decided that. “Let’s see you get all nice and hard.”

I sat back on the couch and tried to relax, tried to calm my heart by telling myself this was what I wanted, what I had asked for (indeed, it was), so I looked at her as I took my soft penis in my hand and began to stroke its surface. I caressed my balls with the other hand. Although I enjoyed the sensations, and was very aroused by her presence, I got no reaction from my penis.

A few minutes of this and she cleared her throat. “Maybe you need a little help,” she said, not at all as a question. She unbuttoned the remaining buttons of her blouse and parted the fabric, revealing to me her large breasts cupped rather nobly in an impressive push-up bra.

“That helps,” I said quietly as I resumed stroking my now growing penis. As she squeezed and jiggled her confined breasts for me I continued to grow, until at last I sat proudly before her with a solid erection. The smirk crossing her lips told me she liked what she saw.

“Now let’s see you jerk that thing off.”

A generous older woman

Blessed are those warm, friendly older women who generously use their bodies to comfort young men. Who have outgrown modesty and bashfulness and use their ample endowments for the betterment of young manhood. Selfless, they are.

B fell under the graces of such a woman once. She helped him through a hard time, her gentle hands holding him, her billowing warm bosom resting on his chest. She watched him satisfy himself the way a young man sometimes must, and she did not protest when he reached a resolution to his problems all over her clean linens.

It was late fall and B was in the middle of his third semester of college. The weather was gray and damp and B found himself getting depressed. His good friend and classmate Josh lived with his family in a town nearby, and B asked if he could stay there for a weekend. Josh’s mother was always very kind to B, and her warmth made him feel good inside.

When B showed up at their door with his duffel filled with clothes, Josh’s mother, Evelyn, answered and hugged him tight. She was a good looking woman, her body toned from religiously performed pilates, her breasts large and pendulous. She pressed her breasts against B’s chest and squeezed him. “Josh told me you were having a rough week,” she said. “Don’t worry, we’ll get you feeling better.

After a hot dinner and a conversation around the fireplace, B tucked himself into the big, pillow top guest bed. He slept better than he had in weeks. He awoke in the golden autumn morning light to the creaking of his door. Evelyn peeked around the door, and seeing that he was awake , shut is softly behind her and padded across the wood floor and sat on the edge of the bed. She was wearing her pilates outfit — thin brown sweatpants and a long sleeved white t-shirt — and to B she looked beautiful and inviting.

“How did you sleep?” She asked, smiling down at him in the sun. He told her he slept better than he had in weeks. “That’s wonderful,” she said softly, stroking his cheek. “Do you want me to rub your back before you get up?” B said that would be nice and rolled over onto his stomach as Evelyn pulled down the warm blankets and clean white sheets. He slept only in a pair of boxers, but something about Evelyn’s warmth made him not worry about it.

Hard cocks at the nude beach

Over the summer I made a few trips via ferry out to Gunnison Beach in Jersey. The dunes and wide beaches were a welcome diversion from the sticky hot city. As were the crowds of naked New Yorkers.

My first visit was with a group of friends — which was a great, sunny, nude day — but what I really want to tell you about is my second visit, when I went alone. It was a Saturday and the beach was packed with shiny naked people. People swimming, people sleeping, people kissing, people showing off their bodies, people gazing at others’ bodies. I stripped down right away and took a walk along the beach, to survey the scene.

My end of the beach was a pretty even mix of men and women, and I stopped to watch a group of college girls splash around in the waves. I had to be careful not to watch their bodies too closely, not to notice the way their firm little breasts bounced as they jumped. I didn’t want to get a hardon right there in front of them, a hundred yards away from my clothes, with no way of hiding it. I moved on.

As I moved down the beach the number of men increased, especially the number of groups of men. I started to notice men here and there staring at me, checking me out. They glanced down at my dick and back up at me, smiling. I didn’t mind, so I just kept on walking, my cock and balls swaying softly from side to side.

At some point, the guarded beach ended and the people thinned out. There were only people like me left, strolling. I walked quite a distance down the beach, enjoying the sun and the breeze on my naked body. Enjoying the small thrill of passing people and thinking, I’m naked right now. They’re naked. We just saw each other naked. I thought of what it would be like to pass the same people on the street sometime, and to remember what their bodies looked like without their clothes.

And then I came upon two guys swimming near the shore. They were laughing. One of them stood up and I saw that he had a full erection. I smiled at him and kept walking. I wanted to turn back and watch them. Something about his hardon and the other guy’s presumed hardon was so fascinating to me. It was the juxtaposition of the public beach, the nudity and the arousal I think that got me so curious. I turned around, pretending to look back at something else, and the standing guy called to me, “Hey, you wanna take a swim?”

“Do you think I need a bra?”

Joan looked like this, basically. I mean, at least her torso did.

Joan visited me at the shop where I work the other day, looking very nice. She stops by often, I suspect to flirt with me, although she appears to be in her late thirties. But like I said, she looks very nice.

“Hey there B, how’s it going?” She asked, perky as usual.

“Great, Joan. And you?” I said, really noticing how nice she looked, fresh and pert with her dirty blonde hair and bright blue eyes. “You look great today, by the way.”

“Oh, thanks. So sweet. I usually wear dresses in the summer, but I thought I’d try this top out today. What do you think?” The top was a thin cotton lavender tank top-ish kind of thing with some elastic business in the neck area that made it scrunch between her breasts. Basically unremarkable, except for the fact that she wasn’t wearing a bra — and her breasts were quite remarkable. I gazed at her chest, pretending to formulate an opinion about her top.

“I think it looks great on you. Very summery.”

“But do you think I need a bra with it? I mean, am I showing too much?”

“No, it’s very nice this way. I think the liberated look is in. It’s very sexy.” I said. Her breasts looked great. They’re probably c-cups, firm and buoyant for her age, and through the thin cotton I could see her puffy round nipples.

“But I’m afraid I bounce around too much. Here, watch when I walk.” She walked over to the door and back again, her breasts bouncing and swaying under the top. I watched purely out of concern for her image as her nipples traced separate patterns around the cotton.

“It’s not that noticeable,” I lied. If I had seen her on the street I probably would have tripped over myself.

“Oh you’re sweet. I won’t worry about it. I feel sexy, anyway.” She laughed, her face lit up and she slayed me with a sultry gaze from her big blue eyes. Maybe I imagined that, but she slayed me nonetheless.

You are the sexiest woman I have ever seen, I wanted to say. Take me to your apartment and fuck me. I will kiss your breasts while you pull me deeper inside you. I want to feel your milky skin against my body. I want to feel your nipples harden between my lips.

“You should feel sexy,” I said. “I think you’re beautiful.”

“Thanks B. If you keep talking like that I’m gonna take you home with me.” She smiled softly.

B

Young liberated women, Part 1

Over the weekend I visited an old friend in Philadelphia. She goes to a small liberal arts school there, and lives with three of her classmates. In all, there’s Jenn (my friend), Quinn, Rebecca and Tati. Jenn warned me before I left Brooklyn that her roommates were rather liberated women, which after a bit of questioning turned out to mean often naked. That’s fine, I said, I’m not one to be offended by a little nudity.

I arrived friday night to find the girls drinking sangria in their unreasonably hot and muggy apartment. Jenn introduced me, showed me around, and explained that Tati is morally opposed to air conditioners. “You’re lucky we’re all fully clothed,” she said. “Most nights like this we’d have stripped down by now.” Lucky indeed, I though.

Back in the living room I was handed a perspiring glass of sangria and joined the conversation. Circumcision, Quinn was arguing, destroys the most sensitive areas of the penis, and ought to be considered mutilation. “What’s your take on it, B?” She asked. I had just sat down and all four of them were looking at me, waiting for my opinion on circumcision. I said I agreed with Quinn, and they went back to discussing it amongst themselves, giving me a moment to survey the scene.

Quinn, the apparent leader of the group, was tall and golden haired, with a smart sarcastic glimmer in her eyes. Her lightly tanned skin glowed against her gauzy white summer dress, and when she leaned forward for her drink the low neckline of the dress fell forward showing us most of her equally luminous breasts.

On stage, showing off her ass

Gotta love American Apparel girls

Today I stopped into an American Apparel in Brooklyn to innocently try on some shorts. The store used to be a theater, and the extremely clever designers decided to put the dressing rooms on the stage. (Dressing rooms might be a slight overstatement; they’re more like small enclosures of see-through fabric, separated from one another by even sheerer sliding curtains. On a stage.)

I found some shorts and the floor girl put me in one of the enclosures, leaving the curtain separating me from the empty next room open. As I pulled on the first pair of shorts, a girl with an armload of shiny dresses threw open the curtain and stepped into the next room. “Oh hi, sorry,” she said. “I didn’t mean to bust all in here like that.” Then she pulled the curtain between us shut, leaving a big gap against the wall. I could see her outline through the thin fabric.

As she undressed she answered her phone. “I’m just trying on some sexy dresses right now. Yeah, like ones that’ll make him nice and hard.” She laughed and hung up the phone.  Once she had her first dress on she threw open the outside curtain again and stepped out to look at herself in the big mirror on the stage. I could see her reflected in my mirror, and the dress was clearly far too small on her. It didn’t cover her big round ass, and her voluptuous breasts looked like they were being poured out the top.

“Hey, girl! How does this look on me?” dress girl yelled at floor girl, who walked over and surveyed the scene.

“I think it’s a little small on you to be honest,” she said, looking at the pleats of the skirt perched on the girl’s generous ass.  “Let me get you a medium.”

“I need a man’s opinion,” dress girl said. She turned to my room and poked her head in. “Hey, tell me what you think of this.” She stepped back into her room and spun around for me. “Too short?”

Coffee, tea or me? or Stewardesses gone wild

Her's were more like the ones on the left than the ones on the right.

When I got on the 6 train this evening I found myself amid about ten young, loud, drunk flight attendants. All girls. All fairly attractive. They were squealing and yelling, the topic of conversation: how they routinely manipulate men using their breasts. Not kidding.

Now, before I get all into it, let me tell you that I am very aroused by the idea of a woman flaunting her body to get what she wants. Probably because I wish it would happen to me a little more often. No, that’s definitely why. I want someone to lean towards me seductively, squeezing her cleavage together and ask for my seat on the train. Or for someone to press her breast against my arm as she asks for a cigarette. But of course, my pleasure.

So the stewardesses (is that PC? No one cares? Okay) went on about the power in their bras as I looked them over. They were all dressed up for a night on the town — a look which primarily involved more makeup than ought to be legal — but one girl stuck out to me in particular. She was slim and simple, pretty in a Midwestern way with short brunette hair, and a dramatically plunging neckline that displayed to me about two-thirds of her small, pert, creamy-soft breasts.

Note: I had to hold my book in an awkward position as an alibi for staring in the direction of her cleavage as the train bounced along.

Midwestern girl was laughing as a busty blonde girl told the story of when she flashed a hotel guy in order to secure a room with a balcony. “That’s amazing!” Midwestern girl squealed. “I’ve never flashed anybody! But I want to!” She burst out laughing. Blonde girl told her she really ought to give it a try. Such a rush.

“Do it!” Interjected a tall girl with long black hair, apparently misunderstanding the conversation. “Show us those titties!” She laughed a crazy laugh, and — amazingly — her sentiment caught on. All the stewardesses were encouraging Midwestern girl, sitting right in front of me, to flash her breasts to the entire downtown 6 train. “You’ll never see any of these people again!” Reasoned blonde girl. “We’re flying out tomorrow!”