Crossing the Rubicon


It was a summer job, the summer after Lucas had graduated from high school. He needed the money for college so when his local video store – there still was one – advertised for an evening assistant, he applied and was hired. It wasn’t very demanding. The internet and Netflicks was taking over, and there were only a few customers most evenings. So mostly he watched videos and read.

Anna came in about 8pm one evening. She was thirty-something, with shoulder-length dirty-blonde hair, 5′ 9″ or so, 130 Ibs, slim. Attractive and curvy, but not out of proportion, her figure displayed well by the pants and tshirt she was wearing. They were emblazoned with the name of the yoga studio a few doors down.

He was attracted to her, in spite of their age difference. He’d seen her walking past the store on previous evenings.

He’d been to yoga at the local gym. It was challenging, as he wasn’t that flexible. And he was distracted by the predominance of lithe women in tight-fitting clothes in every yoga class. He invariably stared, trying not to be obvious.

She put her yoga mat on the counter. “Hi, Lucas,” she said, reading his name tag, “Do you have…?” She mentioned the name of a recently released European film.

“I need it for a film class – night school,” she said. “He’s an interesting director. I have seen his other films, just not this one.”

He looked in the database. “Not in this store. But it’s available in our other location across town”. He told her the address. “Too far to go,” she said. “I need it tonight or tomorrow night at the latest.”

He wondered about the proprietary of what he was about to suggest. “I could get it delivered,” he offered. “Could be here tomorrow. I could…call you…”

She brushed her hair back and smiled. “That would be soooo helpful. My address and phone number are in the store computer – Anna Richards?”

He typed in her name, saw there was only one Anna Richards with an address not far from his house. “You’re at…” She confirmed the address. “Here’s my cell number.” She gave him a business card.

He stared after Anna as she walked out the door, her backside nicely framed by the yoga pants. She turned around and smiled again just before the door. “Thanks again, Lucas. Talk to you tomorrow.”

It was a fiction, the suggestion that the video could be transferred between stores quickly. It usually took a week. He’d have to go and get it himself in the morning. It was a little despairing, he realized, to go to this much trouble just to see her again. But Anna was very attractive…maybe she’d be his Mrs Robinson?


It was early afternoon the next day when Lucas parked in front of her apartment. He’d not called…in case she said no to stopping by. He wondered about leaving the video in the mailbox, but ultimately he knocked on the door of her apartment. The door opened and Anna was there, in a short black skirt and patterned top that hinted at the contents.

“Hi. I hope I’m not disturbing you. I’ve got the video you wanted – I live near here and it was easy to drop it off, rather than have you come to the store.”

“Well …thank you…that was very considerate. I hope it wasn’t too much trouble. Please, come in…would you like a cup of coffee?”

“That’d be nice. Thanks”.

Her apartment was tidy and tastefully furnished, with art hangings and modern furniture. He sat at the breakfast counter while she made coffee.

“I charged the video to your account,” Lucas said. “I hope that was ok?”

“Of course.” Anna brought the cups over and sat down next to him. He could smell her perfume, and when he looked at her he had to make a conscious effort not to look down at the slope of her breasts.

They made small talk; her job, his college plans, life at the video store, yoga.

He was more interested in her than ever, but had no idea of how to proceed. He didn’t think he could ask her out…it seemed so implausible and he’d just make a fool of himself. As the conversation dried up he realized he was outstaying his invitation.

” I better go,” he said, “Stuff to do before the video store tonight…can I use the bathroom before I go? Too many cups of coffee this morning.”

“Upstairs”, she said, “the ensuite – on the right. The downstairs one is leaking so I turned it off until I can get a plumber.”

He walked up the stairs, found the bathroom and closed the door. He did have a nice cock, he thought, as he stood there looking down. At least judging by what he’d seen on the internet and in the locker room. And the girls at the high school – the ones that had shown any interest – had seemed to think it was fine. Walking back across her bedroom he took in the décor. Green walls, light-colored carpet, a couple of paintings, large bed. Pleasant, functional, nothing too feminine.

In a moment of rashness he went to the dresser, where several of the drawers were slightly Maltepe Escort open. He pulled the top one out further; underwear, plain, simple. The second drawer was more interesting. Lingerie…lacy, black, red, dark blue, skimpy and no doubt expensive. He picked up a blue gossamer bra, imagining Anna’s breasts inside, imagining undoing the clasp, visualizing the bra falling to the ground, her breasts swinging free, begging for his touch. Unconsciously he slipped his hand inside his pants. Replacing the bra he picked up a pair of panties, a leopard print thong, just a tiny triangle of material attached to thin threads. He imagined her lying on her back, like Anne Bancroft, wearing the thong but with her legs wide open…waiting for him.

“Having fun?” Her voice echoed in the stillness of the room. Startled, he pulled his hand out of his pants and turned round, her thong still in his fingers.

Anna walked over to him, a wave of perfume preceding her. “You were a long time,” she said, taking the thong from him. She put it back in the drawer and closed it. “So I thought I’d better make sure you were ok. Instead I find you’re some kind of creep perving to my underwear. If you want to jerk off there’s always the Victoria Secret’s catalogue or the videos in your store. Do I need to call the cops or are you going to leave with no trouble?”

“It’s not that,” he stammered, “it’s… it’s…I’m so sorry. It’s just…when you came in the store…you are so pretty…and you looked so sexy…I’ve seen you several times on the street, going to yoga.”

She began to understand. “You fancy me.” It was a statement, not a question. “That’s why you arranged for the video…which arrived very rapidly. Tell me – was that normal?”

“They said it would be three or four days…you needed it…so I went over this morning and picked it up.”

Looking down she could see that he was tumescent inside his pants. “Clearly I do have an effect I see,” she laughed. “It’s very flattering. And you’re a cute boy,” she said, looking closely at him for the first time. Nice-looking, dark hair, a little taller than her, a worried face.

“You’re a bit young for me though. What are you? Eighteen?”


“And you like my lingerie? Did you imagine me in it? And taking it off for you?”

Reaching down she rubbed her hand several times up and down the outside of his pants.

It was too much for him. The look and feel of her underwear, the wafting perfume, being caught, her hand on his pants and of course the fantasy of fucking her that was playing on endless rewind in his mind … he went past the point of control, and with an “oh” he erupted inside his underwear.

The spreading stain on the front of his pants telegraphed his accident. “Oh,” she said, trying not to laugh, “I’m so sorry. I really didn’t mean to do that.”

“I’m so embarrassed,” he said, “please don’t tell anyone about this. Let me clean up a bit and I’ll go. I’ll never bother you again.”

“It’s all right,” she said reaching out to take his hand. “Really. It’s actually quite charming that I can have this effect on you. Look, I don’t have to be at work for several hours and I can wash and dry your clothes first. No one will ever know. Why don’t you go into the bathroom and take off your pants and underwear and pass them out? There’s a robe there behind the door you can wear. You can have a shower if you like.”


She knocked on the door and he handed out his clothes, tightly rolled in a ball. She handed him a towel in exchange, and going downstairs put his clothes in the washing machine.


He turned off the shower, dried himself and put on her robe. As he tied the sash, there was a knock on the door.

“Can I come in?” Anna said. He opened the door and she entered. She had changed her clothes and was also wearing a robe.

“Lucas,” she said, “we can…if you want to…” and she let the robe fall open.

She was wearing the leopard print thong, and a matching low-cut bra. The thong barely covered her pussy, and her breasts were half exposed. Without conscious instruction his body took this all in, and responded instantly with a rush of blood to his penis.

Speechless, he kept looking at Anna, unsure what to do. She reached with one hand through the gap in his robe, and found him becoming hard again. Slowly she began to massage him; he wasn’t John Holmes, but he felt big enough and her hand could only just fit around his girth as he grew under her touch. Taking her hand away she reached out, putting her arms around his waist and pulled him in, so that his cock was pushing up hard against her mound.

“Kiss me. Touch my breasts and my pussy. Put your fingers inside me. You know you want to.”

He didn’t really know what to do or how to do it. He’d not had much experience with girls. A bit of kissing, Anadolu Yakası Escort some mutual groping, but he’d never seen a real woman naked. And he certainly hadn’t put his fingers anywhere near a woman’s pussy.

Anna realized his uncertainty and stepping back took his hand and put it on her thong. “I won’t bite,” she said pulling his head down and kissing him on the lips, with just a hint of tongue.

“You taste sweet. Let’s go to the bedroom.” She walked away, letting the robe fall to the floor of the bathroom. He followed, mesmerized by the sway of her ass cheeks, outlined by the strings of the thong.


“Sit on the edge of the bed”. He sat there, the robe falling open, his penis standing painfully erect. He was shaved down there; something she had not expected. She pulled the robe off so he was naked.

Anna knelt on the floor. “Before we do anything… you really are eighteen?”

“Nineteen,” he nodded, dry-mouthed. “Good,” she said, “then this is perfectly legal…at least in this state,” and she bent over. Taking his cock in her hand, she put her mouth on him and started to move her head up and down his shaft, moving her hand at the same time, slowly building up speed.

Lucas lay back on the bed. He thought he’d died and gone to heaven. The erotic sight of Anna mouthing his cock, together with the intense stimulation of her tongue and lips, was almost too much. He couldn’t stop squirming on the bed, raising his hips to thrust into her mouth as she moved up and down.

“You like that,” she said. ” Boys always do. I think you’ll like this as well.”

She removed her mouth from his penis, letting his erection fall onto his stomach. Bending lower she licked at his perineum, then moved to his testicles and slipped them into her mouth like candy, first one and then the other, sucking them gently, taking turns, one at a time, as he gasped like the proverbial stranded fish. Lucas was in agony…or ecstasy…he wasn’t sure which, but his penis was harder than he could ever remember. Anna kissed her way slowly back up his shaft, licking all around the engorged purple head before easing her mouth over the glans, using her tongue around the raised ridge. “Oh God,” he said, tensing involuntarily every few seconds. “Oh God, Anna… If you keep doing that I’m …I’m so close.”

“Not yet,” Anna said, taking her hand and squeezing the base of his cock to slow him down. She removed her mouth. “You can’t come yet. Not till I have. Anyway I don’t swallow…at least not on the first date.”

She rose to her knees and climbed onto the bed, moving to the top. She turned around and sat up against the pillow. He turned around to look at her, and she opened her legs for him, looking in his eyes. It was if she knew his fantasies. The thong barely covered her sex. He could see that she was wet.

“Have you touched a girl down there?” Anna asked. “Have you put your fingers up inside a woman’s cunt? It’s a bit rude, that word, but I like using it. Cunt. Pussy. Cock. Dirty talk. It gets me excited,” she said, one hand moving between her legs and one hand cupping a breast. She was still wearing the bra…he found that tremendously exciting as well.

“No,” he replied breathlessly. “I’ve never seen… a girl’s…a woman’s…pussy…this close up …only…on the videos.”

“Come closer,” she said, and he climbed up onto the bed, kneeling between her legs. Reaching down she moved the thong aside. He saw that she was shaved, and he could see her labia, pink and plump and moist. “Touch me. Put your fingers in me…carefully,” she said, “women like that…we are really sensitive there.”

He tentatively placed his hand between her legs. Taking it she helped him put one finger, then a second, into her warm slit, simultaneously silky and tight and wet. She started to move his fingers in and out and he understood Anna wanted him to continue.

“Oh yes,” Anna said, her hips pushing back in an age-old rhythm. “That’s it…in and out slowly, as if you were fucking me.” She pushed her mons against his hand in response to his actions. Reaching down, she began to stroke her clitoris as he watched. “It’s like your cock,” she said in between gasps, “it’s very, very sensitive… especially to being licked and sucked.”

She took her hand away and pulled his head down between her legs. “Lick me please…right there.” He could smell her arousal, a pungent musky scent as he leant forward. “Yes yes yes…right there…don’t stop with your fingers.”

He could feel her excitement growing as he licked her private places. Putting her hands on his head, she held him there as he pleasured her, his tongue moving up and around the little bud, and down into her wetness. He’d never seen a woman come before, but he could tell she was approaching orgasm.

“Oh baby…I’m going to come,” she moaned and pulled his head deeper between her legs, forcing İstanbul Escort him against her womanhood, her clit against his tongue, and he could feel her pussy contracting around his fingers as he moved them in and out and he kept licking and then her orgasm took hold and her legs began to shake. He looked up and could see that Anna had her eyes closed as the pleasure flowed through her, a look of ecstasy on her face and then she was over the top, sinking back against the pillow, her legs falling open again. He removed his fingers gently and lifting his head lent forward and kissed her gently between the cups of her bra, her skin hot and sweaty, glistening.

“Lucas…ohh Lucas…that was…”

He sat back on his knees, his penis swinging, still hard and insistent. With post-orgasmic languor she reached out and gently squeezed him. “I guess we’d better take care of this. I wouldn’t want you to have another terrible accident at the store thinking about me.”

She began to massage him, moving her hand up and down his shaft. “So…have you watched the adult videos in your store? The ones where the man comes over the woman’s breasts? Would you like to do that? Come over my tits?”

Oh yes he said…

“Come closer – yes, kneel right between my legs. I want you to shoot your load over me. I really like to watch a man play with himself. It makes me so hot.”

Removing her hand from his cock, she took his put his hand and out it on his penis. “Masturbate for me. Masturbate for me and come over my breasts.”

It had to be a dream and he’d wake up soon.

He continued stroking himself, all the while watching her, as she looked down at his groin, her lips open in anticipation. He saw that Anna was touching herself again, although without the same urgency. She watched his growing tension, his swollen cock straining and jerking as he rubbed himself up and down, and she could see his balls start to contract upwards as he approached his climax.

“Let me finish you”, she said.

Anna cupped his balls with one hand and gripped his cock firmly with the other, rubbing the frenulum with her thumb in a circling motion as he teetered on the edge of orgasm. She aimed his cock over her breasts and breathed, “Let it go”. At the same time she pushed a finger gently into his puckered hole, maintaining a slight pressure there.

His cock twitched upward in her hand, a white stream arching through the air, spattering her neck and her breasts and running down into her cleavage, clinging to the smooth flesh as more semen squirted from his penis. As she continued stroking him, a second ejaculation, then a third spattered heavily over her breasts and her bra as Lucas groaned with the pleasure of his release.

“Oh my God,” she said, ” You were really excited.” She looked down at her streaked breasts, the semen pooling there, her mouth open in amazement.

She leant forward and took his softening cock in her mouth and Lucas shuddered with the intensity of her action.

“Let me clean you up. You’ve made a big mess.”


They lay on the bed, facing each other, cuddling, and she turned to face away. “Spoon with me.” She pushed her ass into his groin, moving it around until she sensed a reaction in the form of a growing erection. ” Wow,” she said,” you’ve come twice and you’re ready for more… I don’t think we have time for round three. I have to be at work…put your arms around me.”

He reached his left arm around and it naturally found her breast in the bra; he cupped this, gently caressing the material until he felt the nipple harden. She pushed back into his groin, feeling his penis between her cheeks. She imagined being on her knees, head down, his big stiff cock driving into her from behind…she reached up to hold his hand, the hand that was on her breast, giving it a squeeze before disentangling herself and standing up.

Lucas turned on to his back to look at her as she knelt over him. Leaning down, she kissed him on the lips and then all the way down, ending with kissing his cock.

She raised herself up and looked down at him.

“I have to go to work and I need a shower. I can’t go with your come all over me.”

She walked to the ensuite. He watched as she casually reached behind her and unsnapped the bra, letting it fall to the ground as she walked through the door. She stopped, stepping out of the thong, with the comfortable intimacy of a woman sure of her body.

Anna looked back at him. “This was really nice; maybe we’ll do it again. Put your clothes in the drier. I have to go, but you can stay and when they are dry let yourself out… and call me in a couple of days.”

The Rubicon had not yet been crossed, but a toe had been very firmly dipped in the water.


It was several days later when Lucas dialed the number Anna had given him. He half hoped it would go to voicemail. Anna answered on the third ring. “Hullo?”

“Anna, it’s Lucas. You said to call.”

“Lucas…I wondered if you would. If not I was going to come by the store again. Are you…all right…with what happened the other day? I imagine that was a bit surreal for you.”

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