Captain’s Woes Ch. 07

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When Dan got home, he hopped into the shower, feeling great. Having finally fucked Dani, he felt on top of the world. He would have stayed to play with her some more, but he had an appointment, and Dan hated to disappoint.

Fifteen minutes later, clean and confident, he was standing at the door to Miss Kline’s apartment. When she opened the door, she seemed a little confused, and a bit embarrassed. She was dressed in a short, blue satin robe, and her hair was up. She looked a bit disheveled and a little wild around the eyes, and Dan thought she was extremely hot.

“Dan,” she stammered. “What are you doing here?”

Boldly stepping into her apartment, he pulled her close, loving the way her body felt up against his. “You said you were going to tutor me, remember?” He leaned in for a kiss, but she pushed him away, abruptly.

Blushing, she tried to straighten out her robe. “I, that is, I didn’t realize you would be coming so soon, is all.”

“Is there a problem with me being here?” Dan asked. “Because you didn’t seem to mind when I was fucking you on your desk the other day.

“I. . .I. . .I did,” she whispered.

Coming close to her, he trapped her up against the wall, and began to undo her robe. “Then don’t you think we should. . .”

Before he could finish his thought, though, in walked a very attractive, similarly robed girl. She looked to be about the same age as Miss Kline, and although it seemed that she had a great body, she also had a very pretty face to match. Medium length brown hair, green eyes, a small nose covered with the slightest hint of freckles, and two very active dimples, she was donning a brown robe. Her breasts, while not as big as Miss Kline’s, were definitely pushing against the shiny material.

“Michelle, what’s going. . .” she stopped when she saw Dan. “Who the hell is this?”

“Erica, wait,” Miss Kline said, “You don’t understand. . .”

“What?” Erica asked impatiently. “What don’t I understand? I drive five hours to see you, and here you are being groped by what looks to be, and please tell me I’m wrong, a student.”

“It’s not what you think. I mean, it’s just that.”

“Whatever.” She whirled around, heading back down the hall towards what Dan assumed was the bedroom. She shouted over her shoulder “I’m leaving!”

“Erica!” Miss Kline yelled, breaking free from an astonished Dan’s grasp. “Erica!” she called, as she ran down the hall after her.

Dan, unsure of what to do, stood there, a little shocked. Could Miss Kline have been sleeping with that Erica chick? That was crazy. I mean, she loved my cock so much, she couldn’t be a dyke. And bisexual?

It had never dawned on him. That’s not to say it hadn’t dawned on him, but not realistically. Down the hall he could hear muffled shouting, and yet he couldn’t help himself. He was very excited by the thought of Miss Kline getting her pussy eaten out by the attractive Erica, and he knew he needed some sort of relief.

Creeping down the hall, he looked for a bathroom to duck into. As he checked doors, he realized that the shouting had ceased. Curious, he slowly went towards the end of the hall, where the bedroom door was half open. Inside his dream had come true.

On the bed, Miss Kline (who Dan started to think of as Michelle, since that was what Erica kept moaning) and Erica Eskort Bayan were kissing. Michelle, obviously trying to atone for her “mistake,” was making her way down Erica’s neck, down to her breasts, which were still hidden in the robe. It didn’t take long for Michelle to rectify that, and soon she was kissing and fondling Erica’s tits, each about the size of peaches, each looking just as soft and delicious to Dan.

He stood in the doorway, and enjoying the show, unzipped his pants and pulled out his now throbbing dick. Stroking it absently, he realized what he had to do. Taking off the rest of his clothes, he walked in confidently but noiselessly. He moved to the side of the bed Michelle was on, and, sitting behind her, began to caress her body and kiss the back of her neck. His touch startled her, and she sat up, breaking off her contact with Erica.

“Dan! What are you doing.”

“Joining the fun.”

“Erica, I’m so sorry, I didn’t realize he was still here.”

Erica stared at Michelle hard, but her eyes softened, and, more tellingly, widened.

“Jesus Christ, Michelle, where did you find this kid?”

“Well, like I was telling you, he’s in one of my classes.” She smiled weakly. Erica got up and walked around the bed, standing in front of Dan. She seemed to have a hard time keeping her eyes off of his chiseled body and large penis. She licked her lips.

“Well, I’m going to tell you what, Michelle,” she said, letting her robe drop to the floor. “I’m going to forgive you, this once.” She turned to smile at Michelle, who seemed a little confused.

“Now go over there and be quiet.”

Michelle was very confused. Erica was pointing to a arm chair in the corner of the room.


“Go sit down like a good girl.” Erica turned back to Dan. “This one’s mine.”

Dan, at first a little disappointed he wasn’t about to fuck these two hot women at the same time, brightened a bit when Erica straddled his lap and they began kissing. Dan didn’t even give a second thought as the hurt Michelle went to the chair, because his hands were full of a very sexy woman.

His hands were all over her, starting with the breasts Michelle had just been sucking on. Her skin was well tanned and smooth, and she smelled great. He leaned his face towards her tits, and let his tongue flick over her left nipple. He paused, and then did the same to the right, letting his right hand caress the left breast. Back and forth he went, enjoying the sounds he was producing with Erica.

As much as she was moaning, though, Erica knew she could always have Michelle suck on her tits, and so she pushed Dan so that he was lying down on the bed. Seeing his questioning look, she smiled.

“This cock of yours is amazing.” She laughed a little. “I haven’t sucked a high school cock for a long time.” Sitting next to him, she let her tongue swirl around the swollen head, causing it to twitch. Grabbing it at the base, she looked like she was examining it, every so often giving it a kiss or a long lick. This teasing was driving Dan crazy, and when he looked over to Miss Kline, he realized it was turning her on as well, because she was absently playing with herself.

Having enough of Erica’s teasing, he grabbed a handful of hair and pushed her face towards his cock. “Suck it.”

Erica didn’t need to be asked twice, and she hungrily attacked his cock, stroking and sucking Dan’s meat. Dan let the sensation hit him, and leaned back, muttering “Oh shit.” Erica was definitely the most experienced cock-sucker he had met, and she knew exactly what she was doing. She played with his balls every so often, something he had never felt before, and he enjoyed it. He wanted more though, and with his left hand, he began rubbing her tits, her stomach, and ultimately, her pussy.

Erica looked into his eyes, and indicated appreciation for his ministrations. Encouraged, Dan reached under her until his hand was on her far hip, and pulled her towards him. Getting the idea, she shifted, straddling his face so that they were in a sixty-nine. Dan took a deep breath, smelling Erica’s sweet pussy, and took a moment. The blow job was almost too distracting, and he needed to get his concentration together before he started to eat her out. It wasn’t too long before he was doing just that.

Lying on the bed in that position, their tan, fit bodies starting to glisten with perspiration, it was quite and erotic sight. Michelle, watching stunned as her friend and her student went at each other, began pinching her nipples with her left hand while her right was busy with her clit. She wanted to join so bad, wanted to feel Dan’s cock once again in her pussy, to feel Erica’s tongue in her mouth, but she was too timid to just barge in. Erica had been so mad, and if this was what was needed for an apology, then so be it.

Dan, sensing he need some relief, began going at Erica’s pussy a bit more aggressively, sticking in a finger as he sucked on her clit. Erica welcomed the feeling, and looked over her shoulder before going back to his cock. Feeling that he could distract her for a bit, Dan switched his finger for his thumb, and with his forefinger now covered with pussy juice, slid it at the same time into Erica’s ass. With both fingers in different orifices at the same time, Erica gasped. He gang-banged her with his fingers and she momentarily forgot about his cock as she threw her head back, her hips bucking into Dan’s digits.

“Fuck yeah!” she screamed. She looked over to Michelle, busy with her own pussy. She looked over her shoulder at a grinning Dan and smiled back. “Enough of this,” she said breathlessly. “I need to feel this monster inside me.” Dan nodded, and Erica quickly turned around so that she was once again straddling him, but this time pelvis to pelvis, face to face. They kissed, savoring each other’s flavor. She broke off, and lifted up her left leg, reaching between her legs to grab Dan’s cock. Rubbing the head across her pussy lips, they both enjoyed that feeling of using Dan’s dick as a sex toy. They both were too impatient, though, and she positioned his dick at the entrance of her pussy, and let his girth slide into.

“Jesus!” She looked down at Dan. “You must split those high school girls in half!” she joked. He didn’t laugh, but instead grabbed her hips and began slamming up into her.

“Fuck! Fuck me! Fuck my cunt, you goddam stud!”

Dan fucked her savagely, thrusting up as she slammed down, getting deep inside Miss Kline’s friend’s pussy. She tried to play with her tits, but the force of his cock was keeping her off balance. Instead, she leaned forward, grabbing the headboard with both hands. With two breasts in his face, he eagerly sucked on her nipples, all the while slamming up into her hot pussy.

Feeling Dan flagging a little bit, Erica sat back up, caressing his hard body. Placing her hands on his firm stomach, she began to rock back and forth.

“Yeah, ride that cock.”

“You keep that dick hard, you hear me,” she warned. Closing her eyes, she grinded her pussy, once again using Dan as a sex-toy.

Seeing her friend riding her student was too much for Michelle. Those pert breasts pointing upward, hard nipples begging to be sucked – it was all more than she could handle. Consequences be damned, she got out of her chair and rushed over to the bed. Hopping up, she faced Erica, and straddled Dan so that her pussy was right over his mouth. She pulled Erica towards her and kissed her furiously, while Dan started licking her soaking pussy.

Caught off guard, Erica paused momentarily, but was soon kissing back as good as she was getting. Their tongues clashed fiercely, and their hands couldn’t get enough of each other. It wasn’t until Dan slid a finger into Miss Kline’s ass that they had reason to pause, because Michelle gasped at the new sensation.

“Dan! That. . .that feels wonderful!”

Looking over Michelle’s shoulder to see Dan finger-fucking her friend’s ass, Erica got an idea. Sliding off of Dan’s cock, she turned around so that she was facing away from both Michelle and Dan, and, once again straddling Dan’s dick, shoved it back into her eager pussy.

“God, I missed that,” she laughed, once again riding Dan. Leaning as far forward as possible, Erica looked over her shoulder at Michelle.

“Lick my ass, Michelle,” she demanded, and Miss Kline was quick to respond. Repositioning herself so that her face was in Erica’s ass, she didn’t hesitate to eat out her friends ass-hole. Alternating between licking, sucking, and shoving her tongue in Erica’s ass, Michelle was both surprised and turned on by how much she liked it. The fact that Dan was driving her toward orgasm didn’t hurt either.

All of the them groaning now, their bodies a tangled pile of sweat, skin, and hormones, Michelle was the first to go. Turned on so much by the show she had gotten, Dan’s tongue and fingers put her over the edge. Sensing her friend’s orgasm, Erica slid back and forth on Dan’s cock with abandon.

“Oh fuck, fuck, fuck, fuck. . .AHHH!”

As Erica’s pussy quivered with contractions, Dan thrust up and began pumping his cum deep inside Erica’s pussy.

Later, after they had all showered, Michelle spread out sleepily on the bed, absently rubbing her clit. Dan leaned over to kiss her, and moved towards the door.

“Excellent study-session, Dan,” she said. He looked back and smiled. Erica, who was also on the bed, got up.

“I’ll walk you to the door.” The walked down the hall to the front door, neither one saying anything. When Dan reached for the knob, though, Erica grabbed his arm. He looked at her, questioning.

She wrapped her arms around his neck and they kissed for a long time. When they came apart, Erica looked directly into Dan’s eyes.

“You were the best fuck I’ve had in a long time.”

“Thank you.”

Handing him a piece of paper, she smiled. “This is my phone number. I’m going to need to see you again.” She looked over her shoulder.


Dan nodded, and wordlessly walked out the door. He was definitely looking forward to that.

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