The Life of a Prostitute

by Doris Joe

  Mr. Meyers went over to Ms. Conrad to discuss Stuart’s panic. They chatted and Mr. Meyers came back to Stuart with an idea.

  “Stuart, please trust me on this. We all must remove our clothes for disinfecting, and we will all support you and help you. Now trust me.” As Mr. Meyers was calming Stuart, Ms. Conrad was informing the girls of the plan and their respective roles. Mr. Meyers brought Stuart into the middle of the room. “Stuart, I am going to place this handkerchief over your eyes. This way you won’t see what is happening. You will only experience the process and the help that everyone is giving you. Trust me. And breathe!” Stuart gave a nervous smile, as he had no idea of what was to come next.

  Stuart allowed the handkerchief to cover his eyes completely. He could feel the presence of others surrounding him, and then he heard Ms. Conrad speak in a very soft, calming voice.

  “Okay, girls, place your hands on Stuart so that he gets comfortable with touch.”

  Caroline placed her hands on his lower legs. Jenny gently placed her hands on his arms. Susan stood in front of him and placed her hands on his chest. He jumped nervously.

  “Take deep breaths as you get comfortable with this nurturing touch, Stuart,” Ms. Conrad whispered.

  James and Allan, the other boys in the group, watched in silence, unsure of where this was heading.

  “Caroline,” Ms. Conrad said, “please remove Stuart’s left shoe.”

  Even though he couldn’t see anything, Stuart instinctively looked downward as Caroline removed the shoe.

  “Girls, place a hand on Stuart’s foot and let it rest.”

  “Stuart, are you feeling comfortable?” Ms. Conrad asked.

  “It’s, it’s okay.”

  “See, Stuart? Relax and be present,” Mr. Meyers said in a low tone.

  “Jenny, please remove Stuart’s right shoe.”

  Jenny did as instructed as the girls then placed their hands on Stuart’s right foot. Stuart took a deep breath as he started to relax. “Susan, please remove both socks.” Once Stuart was barefoot, all the girls placed their hands on Stuart’s bare feet. He squirmed a bit. “Sorry, I’m ticklish there.”

  “Susan, now stand up and unbutton Stuart’s shirt as he takes deep, deep breaths.”

  “I don’t like to be shirtless, Ms. Conrad.”

  “It’s okay, Stuart, just keep breathing.”

  The boys started to grin at each other as they saw their anxiety-ridden classmate getting stripped by three nude girls.

  Susan quickly unbuttoned the shirt and it fell open.

  “Susan, place your hands on Stuart’s bare chest so that he becomes comfortable with your touch.”

  Stuart jumped up. “Your hands are cold!”

  Susan didn’t reply and simply kept her hands on his bare upper torso.

  “Jenny, remove Stuart’s shirt, please. It’s okay, Stuart, you are going to be fine.”

  Jenny removed the shirt and for the first time in his life, Stuart stood shirtless in front of females. Even his male friends rarely saw his bare chest.

  “Girls, place your hands on Stuart’s upper torso.”

  Susan kept her hands on his nipples as Jenny touched his lower back. Caroline placed her hands on his shoulders. They held their hands in place until Stuart relaxed somewhat.

  “Stuart, the next steps will get more uncomfortable, but we all understand and support you. You are among your closest friends in the world right now,” Mr. Meyers reassured him.

  “Caroline, please remove Stuart’s belt.”

  Stuart took another deep breath. He was starting to get comfortable as Caroline took the belt.

  “Stuart, take three very deep breaths.” Stuart did as instructed. “Caroline, unsnap Stuart’s jeans.”

  She did.

  “Jenny, open Stuart’s zipper.”

  She did.

  “Girls, all together, lower and remove Stuart’s jeans very slowly.”

  They did. Stuart’s knees almost buckled. He was glad that at least he couldn’t see their faces as they stripped him. That would be the ultimate humiliation.

  “Girls, place your hands again on some exposed skin. Anywhere skin is exposed is fine so that Stuart continues to get comfortable with your touch." Caroline stood behind Stuart and wrapped her arms around his chest. He could feel her breasts touching his bare back. He could feel her breath on his neck. Stuart had been fine up until this point when he suddenly felt his penis pushing against his white briefs.

  “Can we take a break now?” Stuart pleaded.

  “No way! It’s just getting interesting,” James shouted.

  “Shut up, James!” Stuart screamed.

  “Take five deep breaths, Stuart.”

  He did, and it seemed to relax him a bit.

  “Ladies, each of you, grab hold of a part of Stuart’s underwear.” Caroline held the waistband. Jenny pinched the fabric on his ass to get a grip. And Susan placed her fingers inside the front crotch alongside his legs. She could feel a combination of pubic hair, testicles, and on one side her fingers were in contact with his penis.

  “Stuart, you are doing a wonderful job!” Ms. Conrad said to calm him down. This was the first time a female had made contact with his penis ever. And he liked it.

  “Girls, please pull Stuart’s briefs down to the ground and remove them completely.”

  The girls were filled with anticipation as they slowly revealed his ass, cock, balls, and pubes.

  “Oh my God!” Jenny cried out. “Stuart, you are huge!”

  Stuart was indeed huge. His penis was only semi-hard and yet he had seven inches of cock sticking out. “Thanks, I guess.”

  “Ladies, place your hands on Stuart’s body and give him time to adjust to your touch.”

  Caroline maintained her position behind Stuart as she wrapped her arms around his chest again. This time though, Stuart could feel her pubic hair tickling his ass. He giggled. His giggling stopped when Caroline placed both hands on his penis. He sucked air in and froze. Caroline gently massaged his cock as he resumed breathing and began to like the sensation. Jenny placed her hands on his ass and slowly inched her fingers closer to his asshole. Once Jenny found the treasure, Stuart threw his head back and gasped. Susan cupped his balls. As with all males, the balls are a source of great pleasure and a sense of vulnerability.

  “Girls, each of you should move around Stuart so that you each have the chance to hold his penis in your hands." Stuart felt Caroline’s hands release his cock as a new set of hands were placed on it. Finally, those hands released his cock and he was waiting for the third set. All of a sudden there was a new sensation. It wasn’t hands, but a tongue that was both warm and moist. It began at the base of his cock and ran along the underside of his now nine-inch erect penis. He felt a swirling sensation around the head of his cock until that moist, warm feeling engulfed his entire penis. At least the top half of it. He then felt some hands grasping the base of the penis. Stuart was receiving his first blow job.

  When the girls saw Susan’s technique, they all wanted a turn at bat. All three girls swapped positions until they all had a turn giving Stuart the most amazing oral sex that he could have imagined. Stuart was enjoying it so much that he forgot that two teachers and two other guy friends were watching him have his first sexual experience. But he didn’t care now. He was having the time of his life. And being the center of attention kind of made it even hotter for him. Stuart breathed hard and heavy until he started to arch backwards. Jenny knew what was going to happen and pushed Susan out of the way. Jenny latched on to Stuart’s cock and pumped him and sucked him until he couldn’t hold back any longer. Jenny swallowed every drop of semen that he shot into her throat.

  Stuart was exhausted, but grinning from ear to ear. He pulled off the blindfold to see Jenny licking up the last remaining cum dripping from his cock. Although his cock was softening a bit now, he still had eight inches of thick cock on display.

  “Damn, what a stud, Stuart!” Allan yelled. Stuart bl
ushed. “What can I say?”

  Stuart’s confidence just grew exponentially as he faced his worst fear and was now standing naked, semi-hard, and in front of two nude teachers and three female classmates.

  Everyone’s attention now turned to the remaining clothed boys when all of a sudden there was a banging at the door.

  “Housekeeping! We need your clothing in the blue bags now.” With that announcement, everyone - even Mr. Meyers and Stuart - stripped Allan and James. It wasn’t clear who enjoyed it more. The ones doing the stripping were laughing and clothes were flying everywhere. The boys were overcome as hands forced clothing off and limbs to be lifted, outstretched, and tugged as the clothes had to be removed quickly.

  In a matter of sixty seconds, James and Allan were now standing naked in front of everyone. Mr. Meyers took the blue bags and passed them to the housekeeping staff in the hallway. The housekeeper got a glance of the six naked teens and two adults playing together. She smiled and moved on to the next room.

  Caroline could see the disappointed looks on the boys’ faces. While being forcibly stripped was fun, their lonely penises got no attention. That is, no attention until Caroline and Susan pushed the boys back on the bed and began to suck their cocks with the same enthusiasm that Stuart received. “Jenny the Swallower,” as she was now known, came in to finish off each boy one by one. Everyone else, including the teachers, circled the bed and were an appreciative audience. “You know, guys, your cocks are delicious. Nice and long and thick and hard. But Stuart wins the prize. His cock is amazing."

  Stuart stood up again in the middle of the room, exposed to everyone, and just beamed. It was a Saturday night in September of 1980 at the start of Kelly’s junior year of college. I was visiting Kelly and her roommate Tricia at college. Tricia was looking through the entertainment section of the student newspaper and calling out the various deals, activities, etc., that were going on. She got a big case of the giggles when she shared that there was a porn double feature with “Debbie Does Dallas.”

  The previous spring break was when the dam of sexual tension between Tricia and me had broken and Kelly, Tricia, and I had our first threesome. A few weeks later Tricia broke up with her hometown boyfriend. After that, Kelly offered up my cock to fulfill Tricia’s needs. We had screwed a few times before the summer break but this was the first time I’d seen them together since the beginning of the semester.

  Tricia had been fairly straight-laced when I first met her but, after spending a couple of years at school with Kelly, she had a new outlook on life. And her pussy. I knew her well enough to know that through the giggles about the dirty movie she was actually interested in going. I just let the topic hang in the air for a moment.

  Kelly said, “What do you think, Big Guy? Can you handle taking a pair of cuties to a porno?”

  “If you ladies are interested, I would be happy to be your chaperone.”

  Kelly and Tricia both split a gut at my bullshit. “You just want to get laid and would do anything we ask and you know it,” replied Tricia.

  “True, and not ashamed in the least.” The theatre was a majestic old downtown vaudeville house from the 1920s that, like most others, had fallen on hard times. It was hanging on by its fingernails by riding the short-lived phenomena of when porn went quasi-mainstream.

  The girls got ready. They were both wearing Daisy Dukes. Tricia wore a tight white ringer T-shirt. Kelly wore her close to obscene white tube top. You could make out both of their areolae through the fabric. Their nipples were hard with anticipation. Tricia thought she was incognito because she was wearing a trucker hat low on her forehead.

  Tricia is shorter than Kelly by a couple of inches, standing just about five feet. Her small B-cup boobs pointed straight out and had light pink nipples. Although she would occasionally wear them, she really had no need for bras. Kelly had shaved Tricia’s twat bare the previous spring and I would discover soon enough that she’d kept it shaved over the summer. Tricia’s brown curly hair was kept reasonably short, kind of like a brunette Orphan Annie.

  Kelly’s stunningly long dishwater blonde hair was still hanging to the backs of her knees. Her huge 32F boobs with her hard nipples were putting on a hell of a show in her tube top. Her little bubble butt was built for Daisy Dukes and they looked amazing on her.

  We didn’t know what to expect and were all a bit surprised that the theater was actually fairly busy. I bought a big bag of popcorn to share. The cashier was unabashed in staring at Kelly’s tits during our entire transaction. Actually, both of the girl’s chests were attracting plenty of attention out in the lobby. Since Tricia wanted to fly under the radar, we quickly made our way into the theater and grabbed seats in the center section toward the back.

  We had arrived twenty-minutes or so before the show began and had some time for people watching. I lumped everyone into three buckets. One was the downtown slimy-types. Guys in raincoats. The second, like us, were college students. Horny young fucks. Plenty of couples, but some single guys also.

  The third group surprised us. Respectable couples in their thirties, forties, and even fifties. We could not imagine why in the heck they were there? Weren’t they too old to care about sex? Hah!

  Tricia was in an aisle seat, Kelly next to her and I was next to Kelly. The closest folks to us were two rows ahead and a couple of seats further in than mine. I had guessed them to be their late thirties? The first movie was a typical 1970’s porn. Too much of a convoluted weird-ass plot. It was fifteen minutes before a cock slipped inside a pussy. The sex was okay though, and Kelly thought the cocks were good looking.

  Things changed for Kelly during the later part of the movie. There was an entire scene shot as an extreme close up. Tricia was goofing around putting her hands over her eyes. The guy’ s full-screen hard-on entered the screen and pushed into a waiting twat as it entered from the other side of the screen. It was beyond graphic. We watched the girl’s pussy get wet. Her cream began to stick to the guy’s cock. Hell, you could have counted her cunt hairs if you wanted. It was like we were bugs watching giants fuck.

  I’ll admit that I got hard. Tricia had stopped her goofing. When I looked over at our neighbors, her head was gone. I could only see the guy. Kelly unzipped her shorts and pulled them open. She slipped a couple of fingers into her twat. I noticed there were no panties. Tricia and I were both checking Kelly out and making the wide eyeballs at each other past her.

  Tricia reached over and slipped her hand under Kelly’s tube top and was playing with her tit. The director also got points for sound. We were hearing the sloppy sex as though our face was right in the cunt on the screen. I mashed Kelly’s other tit.

  My eyes were darting around. I needed to know that Tricia was staying cool with the whole scene if I wanted to tap her tight little honey pot later. My read was that Tricia was into the whole scene. Kelly was heading for an orgasm. Hopefully not too loud, but really: who would care? I started catching glimpses of a head bobbing in our neighbor’s lap. I was really wanting to see more of that. I could also tell from the sounds and the music that the movie was heading for the big money shot.

  I saw the neighbor lady's head reappear and she kissed her guy on the cheek. She quickly looked around to see if anyone had noticed her reappearance and I got busted looking right at her. Kelly was starting to vibrate. Tricia had turned toward her and snuggled in close. I knew those two had been having plenty of shared Jill-off sessions at their apartment. I suspected they occasionally shared a bed too.

  The cock on the screen pulled just out of the pussy and, hands-free erupted a decent sized load all over the girl's pussy lips and bush. Kelly tried to squash her “OH FUCK!” but not so well. Both of the neighbors turned and saw her bucking around in her seat as she came. The lady winked at me. I winked back.

  After Kelly came, she was grabbing for my cock and her hands demanded that I pull it out. I handed Tricia the popcorn. I’d dressed for success. I was only wearing a pair of basketball shorts and a T-sh
irt and had gone commando. Once I had my hard-on out, Kelly was slowly stroking me. The first movie wrapped up and the credits started to roll. The lights didn’t go up and we realized there wouldn’t be an intermission as “Debbie Does Dallas” started right away. We were a bit surprised to see the usher walk down the aisle toward the screen and then back past us and out of the theater. I covered my dick with my hands as he passed.

  Tricia snuck out of her seat, past Kelly and me and sat on my left side. She handed me the bag of popcorn. She and Kelly were taking turns eating the popcorn and stroking my cock with their buttery fingers. Not a bad way to watch a movie!

  The neighbor lady and I were still passing glances. She made an “oo” face when she saw I had a girl on each side of me. The shower scene early in the movie had my cock running pre-cum like a faucet. Tricia had been rubbing her thumb around the tip of my cock, playing with my slick fluid. I think a summer without a cock had been too much for her. She slipped to the floor and swallowed my cock in one gulp. Kelly moved her hand to my ball sack. Damn! Tricia’s tight little pie hole had me as hard as steel.

  The neighbor lady noticed Tricia was missing and smiled at me. A couple of minutes later, Kelly slipped to the floor also. Kelly knew how to do magical things with her mouth to my nuts. I was in heaven having those two sucking me. The neighbor lady caught me with a look of total bliss on my face. We smiled at each other. I was on another planet and mindlessly nodded for the neighbor lady to come over.

  I was shocked that she slipped to the end of her row and then quickly appeared in the seat directly in front of me. She was kneeling on the seat, facing backward, smiling at me. She leaned forward and watched the girls working on my cock. Kelly noticed her. She grabbed my cock at the base and stood me up like a flag pole. Tricia pulled off me out of curiosity and discovered we had a new friend. Kelly motioned for the lady to grab my cock.