The Condo Embarrassment - Chapter 2

Jacob removed his $40 fancy sports golf shirt and his T-shirt as well as his socks and shoes and put them in the bag. Courtney lifted the bag and hid it in one of the back bedrooms. Jacob hesitated--knowing that dropping his shorts would reveal the sexy women's underwear that he always wore to his secret trips to the condo. With his embarrassment beginning to soar, he slowly stepped out of his short pants, revealing the unmentionables.

"He's wearing red panties!" screamed Samantha.

All four girls practically kneeled over laughing hysterically. Adele called him over to inspect the panties more closely. She "accidently" brushed his cock ever so slightly with her fingers before pulling on the garment to take a quick glance down at his package--before allowing them to snap back. All four girls, including Courtney, felt the silky fabric before instructing him to return to the center of the room.

"We have to get a picture of this," said Adele. Everyone but Courtney ran to their purses, which were scattered around the room, and then grabbed their smartphones and sat back on the leather sofa and snapped several photos of the embarrassing spectacle.

"I've never seen a guy wearing panties before," yelled Samantha.

"Now lose the panties and throw them over to me," said Hayley.

Jacob turned his back on them and stepped out of the panties. He turned his back around while carefully holding his left hand over his genitals; he then tossed the panties to Hayley with his right hand.

"You need to put both hands down by your side; we want you totally naked!" said an enthusiastic Hayley.

Jacob turned beet red, as now he was totally exposed to all four of the pretty twenty-somethings. No woman had ever seen him naked except his mother when he was a toddler.

"Now, I want you to always maintain eye contact with one of us here on the couch... no looking at the clock on the wall or staring out the window. You focus directly on us. Understood?" said Adele.

"Yes,"

"That's yes, ma'am; not yes."

"Yes, Ma'am, I forgot."

Now the girls' psychological mind fuck would begin in earnest. For the next ten minutes, everyone remained silent as the girls would stare into his eyes and then look at his crotch and back and forth and so forth and so on. When Jacob diverted his eyes, Adele would very sternly tell him to focus, which meant returning their stares. Just when Jacob thought this would never end, Adele says that he needs to lose the pubic hair.

"I'm sorry, what did you say?" said Jacob, hearing her comment but not quite believing it.

"Let's all go to the bathroom and shave all that hair off; it will make your cock look bigger," said Adele.

Everyone but Courtney marched into the master bathroom, where Adele pulled out an electric razor and was quickly removing all of Jacob's pubic hair. He stood there observing both his reflection in the mirror as well as the reflection of the three sexy dancers. Embarrassingly, he was watching them watching him. They all returned to the living room, where the inspection of his pubic area began. After Adele moved her hand across his far lower abdomen, she indicated that he was not smooth enough, and the four of them returned once again to the bathroom. Adele brought out the big guns with shaving gel and a razor blade. After some of the shaving gel fell on his cock, Hayley cleaned him up with a wet wipe; this was yet another embarrassing moment for the eighteen-year-old. After finishing up, all three girls ran their fingers across his now completely smooth and bald pubic area, and they all returned to the living room.

When they walked back to the living room, Jacob couldn't help but notice a large jar of crickets on the floor near the middle of the room.

"So, Jacob, we told you earlier that there would be severe repercussions if you didn't behave or didn't follow our directions. Your margin of error is zero, and you will eat five live squirming crickets if you trip up. They're farm-raised, and we bought them at a pet store, so they're not going to make you sick," said Adele.

Jacob's eyes got big as he stared at the crickets jumping around in the jar. They were dark brown and almost an inch long with beady little eyes and large antennas.

"You mean I'm going to have to swallow them live."

"Well, no, I guess you have to chew them up first, but I guess you could also swallow them whole, but then they would be crawling around in your stomach until they ran out of oxygen. And that would give the phrase "creepy crawling" a whole new meaning."

"Let's move on; if you behave, you won't have to eat them," said Adele.

In the hidden videos that we taped (that have audio as well), you're naked on our beds and then you play with your nipples. You took your ring finger on your right hand and played with your left nipple, and then you took the ring finger on your left hand and played with your right nipple. Now, I want to see you do it."

"Oh, that is embarrassing; that is too embarrassing. You wouldn't make me do that."

"That's fine. I just need to see you reach in the jar and eat the first cricket and then four more." Adele continued.

Jacob resigned to his fate and began rubbing and massaging his nipples, and he also noticed that Courtney now was holding a 4K video camcorder and was recording the festivities. Apparently, she was the designated videographer.

"You're going to tape this?" asked a very surprised and somewhat disturbed Jacob.

"You just asked a question, and what did we tell you about asking questions? "We're going to give you a pass on this one, but you're within a couple of millimeters of eating a bunch of crickets," said Hayley.

Jacob had no idea where all this was going, but the alternative was a lengthy incarceration. Wherever the girls led, he was destined to follow. He was told to continue to massage his nipples for ten minutes with a fifteen-second break during each minute (a fifteen-second break during each sixty-second interval). The girls continued the stare-down--looking at his eyes and then gazing intently at his cock and balls. His eyes remained focused on their eyes no matter how embarrassing; his fear of the live crickets (jumping around in the jar) surpassed his fear of sexual embarrassment and potential humiliation.

"So, how does that make you feel when you rub your nipples?" asked Samantha.

"What, what do you mean?"

"Well, you do it for a reason; why do you do it?"

"Does it enhance your masturbation experience?" asked Hayley.

"Yes, I guess. I mean yes, ma'am."

The girls were absolutely burying him in a huge pile of embarrassment. Adele commanded him to sit on the leather sofa in the middle cushion while she and Hayley sat beside him. Samantha took a seat in the comfortable leather recliner while Courtney continued filming everything with the camcorder. Hayley fast forwarded the aforementioned tape, which showed him illegally trespassing with his parents' duplicate key and entering the foyer and then looking through all their personal effects in the living room. The tape then unveiled Jacob entering Adele's large bedroom and then proceeding to open all of her dresser drawers, looking through her personal effects, handling her panties, bra, black stockings, baby dolls, etc. Jacob moved to the closet, but the camera angles did not provide specific details. It appeared that he was pulling her dresses from the hanger. He also seemed to remove boxes from the top shelves of her bedroom closet and peruse the contents, but then again, the three cameras did not have a good view of the interior of the closet. The video showed Jacob trying unsuccessfully to access her laptop. Jacob stared at the screen (not the laptop but the current ongoing historical video of Jacob's nocturnal condo visits) apprehensively, knowing major league embarrassment and humiliation was right around the corner. In the historical video, Jacob was seen looking at his smartphone.

"Are you checking on our locations here with that app?" asked Hayley.

"Yes, ma'am."

The video then revealed Jacob completely removing all his clothes and attempting to put on a pair of Adele's black stockings; unfortunately, his muscular legs did not quite fit and the stockings tore. Adele pinched him hard in his ribs, causing him to scream "ouch" very loudly. The video continued with him attempting to try on her panties as well as inspecting and sniffing her bra. He discovered a large silk scarf in one of her dresser drawers, and he lay down and began stroking his joystick. Unmistakenly, the silky-smooth fabric of the scarf was driving Jacob to unfathomable levels of ecstasy; he was in the midst of an intense edging session and began making some rather strange sounds. Jacob put his face in his hands as his humiliation and embarrassment rose to exponential levels. Adele had Hayley rewind the tape to watch Jacob's ten-minute amusement park ride as the girls laughed while watching his screams, shrieks, and yelps.

"It appears to me that you are in some sort of combination of laughing, crying, whimpering, and moaning, and then you have these cute little loud yelps every twenty seconds or so. Is that what you see Jacob as well?" asked Adele.

"I guess, I mean yes, ma'am."

"I have never seen a man masturbate that intensely before," said Hayley.

"I think he even has some tears in his eyes, or they are at least moist," said Samantha.

As the tape rolled, Jacob was seen removing the silk scarf, revealing his rock-hard shaft.

"Stop the tape; look at that. Wow, it is rather thick and nice in length too. "So have you ever measured your cock, Jacob?" asked Adele as she placed her hand on his upper right thigh, inches from his love muscle. Jacob's cock was more than half-erect as it was lying parallel to his thigh, and it was throbbing and growing noticeably. The 100 mg Viagra pill, described as the "embarrassment enhancement pill," was performing marvelously.

Jacob paused and took a deep breath and said, "Almost seven inches." He didn't wish to be accused of lying and then have to eat those crickets. He was not lying, and the girls could easily see from the video that he had a rather large, girthy pecker.

"How about the girth and the width, ever measured that?" asked Adele.

"No, ma'am."

"I would really love to; I mean, I bet all your girlfriends really love sitting on that," remarked Samantha.

The remark did not go unnoticed as Adele and Hayley exchanged glances. When all three of them saw his cock for the first time (on film), they described it as "beautiful." It was not only "right sized," but it also sported an adorable, purple-colored mushroom head. The girls had been obviously furious at this blatant invasion of their privacy, but the fact remained that Jacob's dark complexion, rock-hard abs, sculpted chest, 6'1" frame, perfectly symmetrical face, and cute dimples were simply mesmerizing.

"I haven't had many girlfriends," said Jacob.

"How many?" asked Samantha.

"Well, I've dated a few; I guess I'm kind of shy."

"You're not answering our question," said Hayley.

"I haven't had a girlfriend."

"So, it sounds like you're a virgin; is that right? asked Hayley.

"Yes, ma'am."

"Have you ever gotten to first base like touching a girl's boobies?" asked Samantha.

"No, ma'am." The crickets (or a potentially unfortunate incarnation) were frightening him to answer every question quickly and truthfully.

"Wow, I guess that explains why you're so horny, and jerking off seems to be your hobby," said Adele.

Adele then directed Hayley to continue with the video. By this time the video showed Jacob had removed the silky stained satin scarf, and he was vigorously fisting his schlong. His moaning, screaming, and shrieking were reaching a crescendo, and five or six ropes of cum erupted from his cock. The second rope of jism landed on the tan leather headboard of the bed; the others peppered out on his chest or on Adele's bed. Much to the dismay of Jacob, Adele directed Hayley to replay it four separate times. Both Hayley and Adele's hands were laying on top of his thighs. Jacob knew about an hour ago that this scene was upcoming, and Jacob was shaking his head and looking toward the ceiling and wondering why his obsession with attractive young nude women had led to three dozen potential criminal charges, not to mention the scene that was unfolding this Friday morning in the condo. Hayley paused the video right in the middle of his cum shot as his jism hung in the air, and Adele directed Jacob to stand once again in the middle of the room.

"OK, now I want you to tell us about yourself." said Adele.

"What? What do you mean?"

"I mean, we know that you're an eighteen-year-old virgin with a big fucking cock and a pretty nice body as well, but where do you go to school, when do you graduate, where are you going to college, what will be your major, what are your hobbies, and what do you do when you're not looking at porn?" asked Adele.

"Well, I go to XXXXX XXXXXXX (intentionally redacted) high school, and I graduate Monday night." I will attend XXXXXXX XXXXXXXXX (intentionally redacted) University. I plan on studying computer science, and I like to work out and listen to music and watch the old Seinfeld and Big Bang Theory re-runs."

Samantha had relieved Courtney as videographer, and Hayley had been carefully perusing the contents of Jacob's smartphone (that was part of the agreement to keep Jacob out of prison).

"Jacob, I found some very interesting voice memos here, and you know what I'm talking about, so why don't you share with the group what I have found?" said Hayley.

Jacob's mouth fell slightly open as he stared out the window. He was waist deep in embarrassment already, and Hayley was about to add another layer.

Y'all are not going to tell anybody about any of this, are you?"

"No, of course not," said Adele.

"Wow, this is hard. OK, I have recorded several voice mails of my voice while I am masturbating and ejaculating."

The girls giggled at the remark. "He can't even say the word cumming." said Samantha.

"And do you go back and listen to these again when you're masturbating again?" said Adele.

"Yes, ma'am."

"How many of these do you have taped, and how long are they?" asked Adele.

"I guess I have about fifteen or so, about three or four minutes each."

"Well, let's just spend the next thirty- or forty-minutes listening to them," said Hayley.

Hayley then proceeded to play the first recording, and they all listened as Jacob ended the first voicemail with "Oh goodness; oh fuck! Oh yeah! Oh, oh, oh, I'm cumming before finishing with a bunch of gasps and moans.

"Wow, do you always scream that loud when you're rubbing one out?" asked Adele.

"Well, no, I mean no, ma'am; if my parents are home, I stay quiet."

"But you really let it loose when you're alone," exclaimed Samantha.

Hayley noticed that there was some background noise on the tape.

"Is that porn in the background? It sounds like every thirty seconds or so I hear people having sex?"

"Yes, ma'am."

Adele paused, trying to frame her thoughts. "So, I don't quite understand; you have... I guess porn on the TV, but it only lasts for about eight seconds, and then there is silence for a while, and then the porn comes back on for another eight or ten seconds. How does that work because you're obviously busy wanking your pecker during this time?"

These girls were leaving no stone unturned. Jacob sighed as he tried to figure out how he was going to explain this.

"I have made eight-second clips from various porn movies, and then I have an app that runs a photo wall containing pictures of girls; these are interspersed together with the pictures and the porn."

"And of course, all the pictures are pornographic, right?" inquired Hayley.

"Well, not all of them; some of them are like the old Playboy and Penthouse variety."

"You are certainly the connoisseur of pornography," said Adele.

"So, Jacob, have you ever seen a completely naked woman? asked Adele.

"No, ma'am."

Adele instructed Jacob to again sit down in the center sofa cushion; Hayley and Samantha sat on each side of him. Adele walked up and stood directly in front of Jacob and began unbuttoning her tight red blouse. Her voluptuous 32G breasts were stuffed inside of a lacy black bra. She wasted no time in removing her 5-inch-high heels and the black skirt. After she placed her right stocking foot on his left leg, Jacob's stiff member fully blossomed. She lay on the floor directly in front of Jacob (with her butt on the floor and legs in the air with her butt flush with the sofa) and slowly peeled off her nylons. She stood up and then hung her stockings around his neck. She then rubbed her bare feet up and down his legs, which produced more throbbing and bobbing in Jacob's manhood. She then yielded the floor to Samantha, the Lana Rhoades lookalike. Samantha surrendered the videography duties back to Courtney, who needed respite from holding the camera for a significant period. Adele sat down on the sofa to the left of Jacob and tossed her black stockings over Jacob's right leg. She traced her fingers across his now bare pubic area and gently massaged his nipples. Jacob's flagpole was at full attention and was unrepentantly bobbing and throbbing.

Samantha took Adele's place on the living room floor just four feet in front of Jacob. She slowly pulled the light blue satin crew-neck sleeveless blouse over her head, revealing her 34B chest nicely packed beneath a blue bra. She kicked off her white open-toed high heel with them landing at Jacob's feet. While holding both of her hands on the top of his head, she stood directly in front of Jacob and instructed him to slide the white capri pants down on her silky-smooth tan legs. She stepped out of the pants and told Jacob to throw the pants on the floor. She let her right foot hover over Jacob's engorged cock until she placed her foot on his taut stomach. Her piercing blue eyes seemed to gaze straight through his soul. Samantha removed her bra and shook her tits right in his face. She then settled into the sofa seat just to the right of Jacob, where the entire length of the left side of her sensual body was in contact with Jacob's. She draped her left hand over Jacob's shoulder.

"You're up next," said Samantha as she gestured toward the twenty-five-year-old Hayley. Her striptease went much faster than the previous two. Since she was not wearing a bra, her spectacular 36Cs came into view as she pulled the pink tank top over her head. In one quick motion, she threw off her leopard print open-toe mule heels and stepped out of her short denim jeans.

"Look, no panties," exclaimed Hayley.

Jacob's eyes feasted on his first live nude woman. With Adele and Samantha snuggling with him on both his left and right and a fully exposed nude blonde beauty standing four feet in front of him, his prick continued dancing in the air. Adele and Samantha's hands caressed Jacob's chest and nipples. Hayley leaned over and lightly cupped his chin in her hand. By the looks of Jacob's purple monster, the 100 mg Viagra pill that he swallowed earlier was working as advertised.

"You're so horny; you can't stand it, can you?" whispered Hayley in her seductive voice.

"Yes, yes, I mean yes, ma'am." Jacob mumbled--barely able to get the words out. He was slightly embarrassed by the boldness of his confession.

Now Jacob was surrounded by three voluptuous babes in various stages of undress: bra and panties (Adele), panties (Samantha), and the totally stark-naked Hayley. Adele possessed the most attractive rack of the three girls, and his genitals were sinfully craving the unveiling of the massive 32Gs beneath her black bra. Samantha and Addle retreated to the back bedrooms, momentarily leaving him only with the au naturel NSFW Hayley and Courtney, who was still diligently filming the entire spectacle. Jacob noticed a rather large fraternity flat paddle with air holes leaning against the wall separating the small breakfast room from the kitchen.

"I didn't see that before." Jacob said as he pointed toward the paddle.

"You're going to meet him later," said Hayley.

"What? What do you mean?"

"You know what I mean." Hayley replied with this glaring vengeful look in her eye.