Birthday Boy Sequel - Weeks Later

It felt wonderful to feel her thighs against my hips, to feel my hard cock slip easily into her. I couldn't see her face in the dim light, but that didn't matter. Then, just as I was all the way in, I woke up. It had been six weeks since my breakup with my girlfriend Carol, and then my pleasant encounter with a girl I met online named Clarissa, who was the girl in the dream. I had thought of her a few times, but this was the first time I had seen her in a dream. I tended to remember dreams, and sex dreams were rare. I wanted to call her and see her again, and I didn't. Part of me still had hesitations about seeing an escort, but it wasn't the part in my pants, or apparently my subconscious.

I had had two dates since my birthday, when I found Clarissa, and neither went well. The first was with a woman about my age who was a friend of a friend, and she turned out to be a compulsive talker. Yes, I do want to know about you, but save some of it for the next time we meet. And you might want to know a little about me beyond what limited information my friend might have told you. The other was a pretty brunette a few years younger whom I met in a bookstore. While she was better, it was clear we had very little in common other than a love of science fiction. Both dates ended in a good-night kiss and nothing more, although the talker seemed interested in a second date. I wasn't, much as I didn't like disappointing my friend who had introduced us. I had the sense she knew enough about me to figure I was a good catch, if only financially. I'm not sure why he thought we would be a good match, and I didn't ask.

On my way home from work I got $1000 in cash out of an ATM, then went to a big-box store I don't usually frequent and got a cheap pre-paid phone. When I got home, I brought up the Web site on which I had found Clarissa. She was still on there, still looking hot. I hadn't saved her number, so I was glad to find it again. I went for a swim in my indoor pool, then made a light dinner for myself. I went back to the Web site later and looked at her and other women. Finally, I called, after considerable hesitation. Once again, that very feminine voice answered, "Hello." I was a little surprised she picked up; I figured she might be busy at that time of the evening.

"Hi Clarissa, this is Jack. I saw you several weeks ago, and I'd like to see you again."

There was a slight pause, then, "Oh, right, you're the engineer. Can you come by tomorrow at 3:00? Or is that too early?" She probably figured I'd be at work, tomorrow being a Thursday, but I have some flexibility.

"No, that would be fine. Text me your address again." I was glad she suggested an early "date," since that would probably mean I was her first for the day. Out of how many, I wondered. And what would she be doing afterward, that she suggested an early time? I put the thoughts out of my mind.

"I'll do that. Would you be interested in a little something extra? I have this friend named Emily."

Well, that was interesting. "Maybe. Tell me about her," I replied. This would be a first and also a fantasy come true, but I'm by nature cautious.

"She's around 30, shorter dark hair, um, voluptuous, great personality. And she is a very good friend. I think you'll like her." The way she said "good friend" spoke volumes, and I was excited. She didn't need to say that it would cost more and I didn't ask.

It was not easy, waiting. I swam for half an hour, then spent the rest of the evening reading something technical, or trying to. I was tempted to take care of my hard cock but resisted, since I would be seeing Clarissa tomorrow. Or would I? I considered texting and canceling, but I didn't. The next morning I went through my usual routine, but distracted thinking about Clarissa and Emily and what we had done, and might do. I was also again distracted by minor moral qualms, but rationalized it with the "consenting adults" clause.

My day at work was so busy I barely had time to think about anything else until I realized it was 2:00 and I needed to get going soon. I'm never late. This time I didn't bother with the extra wallet, and I had the cash with me. Nobody even blinked when I left, since I had been there since six, and despite my distraction had been unusually productive.

The drive to Clarissa's apartment got me apprehensive. What about this friend? What if there were problems? What if someone catches on? I parked two blocks away so I could walk and clear my head, but I was still nervous when I rang the bell. I let that all go as soon as Clarissa answered, and actually felt good when she opened her door. She was as gorgeous as the last time, wearing a white blouse and short red skirt. She led me to the living room where Emily rose from the sofa to greet me, smiling. She was attractive in her own way, less to my taste than Clarissa, but I was sure we all could have a lot of fun. Her attire matched Clarissa's, all of it, as I soon saw.

There was no real need to break the ice, and Clarissa got to the point. "Let's get you out of those clothes." Before she did, I took ten crisp bills out of my wallet and put them on the coffee table. She glanced at them, then led me to the bedroom, Emily following, and undressed me while Emily watched. She gave my hardening cock a small kiss and suck as she took down my briefs. Then they undressed each other, removing, finally, matching bras and panties. Cute. I got hard as I watched, which drew appreciative glances.

"We want to put on a little show for you, if you like. You can join any time, of course," said Clarissa.

Once I agreed it was obvious that they had planned this, maybe done it before. They both sat on the bed and spread their legs, giving me a nice eyeful for a little while. They both spread their lips and touched themselves, feigning pleasure. Or maybe not; perhaps they really enjoyed it, since they were "really good friends." I stroked my stiff cock a little. Clarissa pinched Emily's big nipples and got them hard; hers were hard already. Emily's breasts were big and sagged a little, which told me they were real. Later I confirmed that as I squeezed them.

Clarissa moved out of the way so Emily could get on the bed, a pillow propping up her head. Clarissa knelt between her legs and bent over in classic "slut position," face down, ass up and pussy open, and licked Emily's clit. I was so aroused I almost forgot, then got a condom off the dresser and put it on. I got behind Clarissa and eased in. She started a little, but I'm sure she wasn't surprised. In that position I couldn't see what she was doing, but it must have been good because Emily was moaning and moving her head from side to side. After a few minutes of pumping Clarissa's cunt I felt myself getting close, and pulled out to watch the show up close. It didn't take long for Emily to cum, and I was sure that wasn't faked.

Emily, panting, her legs spread, motioned to me. I feasted my eyes on her shaven cunt, with a fairly large clit swollen from the attention and big inner lips that looked as though they would probably hang down outside of her outer lips. Any pussy is a pleasure to look at, but I like some better than others. I took Clarissa's place and slid my cock into her, up to the balls in one thrust, and stayed there for a full minute, enjoying being in her. She had great muscle control, and when she realized I wasn't going to thrust right away, used her cunt muscles to suck me. That was amazing. I started thrusting and felt Clarissa behind me, fingering my ass and balls. I was ready to cum in a couple of minutes, but she stopped.

"There was something we discussed last time that I told you I wouldn't do, but said I might next time," she said.

"Oh, you remembered. Yeah, that would be hot."

"Well, I might consider it. But Emily loves it. She's ready."

Emily brought her legs up high and showed me her tight pink anus, wet from her cream. "You need to be gentle, but I know you will." Clarissa handed me a bottle of Astroglide and said, "You'll need this."

I applied the lubricant liberally to Emily's ass and to my sheathed cock, then put the tip against her nether opening. Clarissa, sitting on the bed, helped guide me in. The tightness was amazing, and once I was all the way in, Emily moved to encourage me to thrust. I started pumping in and out, feeling great, until I felt something cool, hard, and lubricated against my anus. Clarissa had put on a strap-on with a small vibrating butt plug and proceeded to work it into me. It took about two minutes of me fucking Emily and Clarissa fucking me to make me cum hard in Emily's ass. Wow!

I lay back, panting, and it took a couple of minutes to recover my senses. "You girls are incredible," was all I could manage. Clarissa took the condom off my still-stiff prick and remarked on the size of the load. "Looks like getting pegged made you cum hard. Ever done that before?"

"Just a little play, nothing like that. I'm more used to prostate stimulation behind my balls, not internal."

"Glad you liked it," said Emily. "A lot of men do," added Clarissa.

Then she pushed a limit when she said, "So would you take a cock up your ass while you're fucking?"

"Not a chance. What was hot was not just the feeling in my prostate but that a hot woman was doing it."

She seemed a little relieved to hear that, and I later guessed that bisexual men are riskier. "But you like watching girls play with each other, and that's okay."

"Of course. For that matter, other men having sex with each other is okay, just not for me. But I like watching women do it because, well, they're women." She chuckled at that.

The two of them played with me a little until I was hard again, stroking my balls and shaft, or sucking a little. At one point Clarissa said to Emily, "See. I told you."

Emily replied, while Clarissa sucked me, "You sure did. So your turn now?"

Clarissa asked me, "What do you want now?"

"So have you considered letting me have your ass?" I replied.

"I'm not sure I'm ready for that yet, especially with you. You know you're pretty big."

I smiled at the compliment. "Okay, then both of you stand on the floor and bend over the bed."

They did as instructed, and I stood behind them and waited for a count of 15, enjoying the view. I'm sure they were puzzled. Then left hand on Clarissa's ass and right on Emily's. "You're such naughty girls, you need a spanking." I gave them only 10 strokes with my hands, enough to turn them a pretty pink that faded after a couple of minutes.

"Where's that strapon, Emily?" I asked.

She guessed my intent and said, "I have something better." She opened a drawer in the nightstand and got out a small black rubber butt plug with a button on the bottom and put a condom on it. "Do you want to do the honors or should I?"

"Oh, I'll take that. Turnabout is foreplay." I put some lube on my fingers and eased it into Clarissa's ass, taking my time, making sure it was all the way in. Emily watched and played with herself, sometimes pinching her nipples, sometimes stroking between her legs. I could smell her arousal. When the plug was in place Emily got another condom and put it on me. Clarissa wiggled a little, maybe a little uncomfortable. I planned to remedy that. I pushed the button on the plug a few times until it was on the highest setting.

I slipped into Clarissa's tight pussy, feeling the vibrator through the wall of tissue separating the two passages. I had done this before, but not for a long time, and very few times. It felt incredible. I pumped her until I started to feel my orgasm, then held back, edging myself. There was no edging her, though. She came hard several times.

After a few minutes of giving me a sideshow of her fingering her open cunt, Emily got up and went behind me, but only to stroke my balls and between them, very gently. That gave them what they wanted: another satisfied customer. I came harder than the first time in Clarissa, filling the condom. I pulled out carefully, with Emily's help, and she gripped the tip of my still swollen cock before removing the condom with a Kleenex and tossing it in the wastebasket. I noticed that there was nothing else in it except the first one, so that meant that they were good at hiding the evidence of previous encounters or I was the first one today. Or both. Clarissa turned toward me and took out the butt plug, wrapping it in a Kleenex and putting it on the floor.

I recovered my breath and my senses and thanked them for a great time. Clarissa said, "So did you get what you needed, birthday boy?" I knew she was referring to anal sex, and I said, "Yes, pretty much." I had wanted to take her second virginity, if she was being truthful about still having it, but getting to have anal with Emily was incredible.

The previous time Clarissa had told me about losing her job and also missing sex, which was how she got into the escort business. I asked Emily, and hers was a rather different story. She had an abusive older brother and her parents wouldn't do anything about him, so at 18 she moved out and got a job in another city. Since she had no real skills she could only get low-paying jobs, barely enough to support herself. While she was working at her second one, clerk in a retail store that sold clothing and housewares, an older man had propositioned her. She was shocked and nearly hit him, and he apologized and said he was joking. She didn't much like men at all, so this was all the worse.

A couple of weeks later he was back and she had time to think about it. She also had time to realize that she could barely make the rent at the end of the month. When he went to a fitting room to try on a pair of pants she said, "I'll bet you'll look really good in those," and smiled. He hesitantly smiled back, went into the room and put them on. He came out wearing them and said, "How do they look?" His hard-on was clearly outlined but he acted as if nothing was amiss. "They look great on you," she said, smiling and looking him up and down. She might as well play the game.

"I'll take them," he said, going back to change out of them. He gave them to her to ring up as they went to a register, and slipped her a post-it note with his first name and number on it. She put that in her pocket and finished her shift, wondering what to do.

At home she had macaroni and cheese for dinner. Again. This was getting old. She pulled the scrap of yellow paper out of her pocket and looked at it, put it on the table, and finished her dinner. She left it there and got out her computer and put the number into search. It came up with nothing useful. She thought about it a little more, then moved to the sofa and watched a movie on her aging laptop. She was still considering it when she fell asleep.

She awoke in the middle of the night, worried. Rent was due in two days, and she could barely cover it, and payday was a week out. But what if he hurts me? The store's security cameras will have him. Will that even matter? What if I get pregnant? But the rent is due and that will leave me with 16 dollars to last the week. She made a decision.

On her way to work the next morning she stopped at a drugstore and bought a three-pack of condoms. He didn't come to the store. He was waiting too.

She got home and made beef ramen for dinner, then did a little research on her computer. Girls charged between $100 and $500, depending upon what they did, age, attractiveness, and so on. She figured she should get at least $250. From what she read, at least in this city it was a relatively safe thing to do.

She called him. He answered and she told him who she was, and apologized for her first reaction to him. "Oh, don't worry about that. I misread you, is all, and I'm sorry. But are you interested? You seemed to like the view when I tried on the pants."

"Maybe. Tell me a little about you."

"I'm 42, run a small business that's doing pretty well, and I like to have a little fun now and then."

"What kind of fun?"

"How old are you?" he asked.

"Eighteen as of a three months ago."

"Good, but I'll want to see some ID. Why don't we discuss the details in person? Can you meet me for coffee?" And he gave her an address. She figured it would take 45 minutes to get there by bus and walking, and agreed to meet him in an hour. She realized he was making it safe for her, and also himself.

She left her work attire on, since she didn't really have anything sexy, knowing it didn't matter, and after freshening up and touching up her makeup, was out the door.

He was there when she arrived and they got coffee, and she got a Danish. He paid with cash and left a tip. Good sign, she thought. He steered her to a table as far from anyone who could overhear as possible. He was wearing the pants he had bought from her. After a little innocuous chitchat about her job, he got to the point. The main thing he wanted, at least that time, was oral sex, something he claimed most women didn't like doing. "You're not a cop, are you?" he asked, joking. Supposedly someone must answer that truthfully if they are, but that's an urban myth.

"No. Are you?"

"No. I see you're finished. I'm parked at the far end of the lot, well away from any other cars. It's a Chevy Suburban."

"Oh, do it in there?"

"Yes."

She liked the idea. It would be over fairly quickly and she wouldn't even have to undress. "Sure. How about two hundred?"

"Game on," he said, and slid out of his chair. He had thought she would ask for more, being so young.

"Money first," she said as they walked to the vehicle.

"As soon as we get to the car and I see you're not going to take it and bolt."

The thought hadn't occurred to her, but she was sure he could outrun her. She had no intention of doing that anyway. She might need to do this again.

Inside, the tinted windows hid them and he handed her the bills. He leaned one of the back seats back and unzipped. She took his cock out and had a look. No obvious problems. It was getting hard, and her sucking completed the job. She licked her hand and stroked him, then sucked the tip again a she pumped the shaft. He oozed a little pre-cum and she rubbed that around the tip. "I want to cum in your mouth," he moaned. She nodded as she sucked, thinking, "Perfect. No mess." And in just a few minutes he unloaded as she sucked hard and pumped his shaft. It was a lot, and she had a hard time swallowing it all. She wasn't the slightest bit aroused; this was just a business transaction.

When he recovered he put his soft cock back in his pants and asked for her number. She hesitated, but he seemed nice enough, and it wouldn't be so bad if this turned into a somewhat regular thing. She gave it to him, but realized he had it from her call. He then asked if he could give her a ride home. She thought for a moment and said, "No, thanks. It's not far," and got out.

She considered taking a cab home but thought better of it and went back into the coffee shop until she saw the Suburban turn onto the main street. She walked the other way to a bus stop. She stopped at a grocery store and bought ground beef, a gallon of milk, and other things she had not been able to afford recently.

He called her a week later and asked to meet her at a different coffee shop. This time there were no preliminaries. He gave her the money, then drove to a nearby park. Again, she gave him a blow job in the back of the Suburban.

He asked if she did this often, and told her she was good at sucking cock. No, not much, but she had sucked cock before. She didn't say it had been her brother's.

He told her he had a few friends who might enjoy her services, and set her up with them. He didn't pimp her out; they just paid her. He was glad she would keep seeing him, and she was glad to have the money. She started to like giving blow jobs. She learned that some of the friends were married and were getting from her what their wives wouldn't give them. That surprised her a little. Some also wanted titty-fucking, and she was built for it. Twice she had met men in motel rooms for actual sex, and she got five hundred for that. It wasn't long before she was making over a thousand a week with her side gig. A problem was that it was all in cash.