Sammy CS Pt. 02

Part 1 in my profile.

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All good things must come to an end, and it was something Hannah was not ready to deal with. For about 6 months, Hannah thought of Thomas as a sexual shark because even at the slightest waft of her wetness, he was all over her and ready to go. But then to go from having sex like rabbits almost daily, sometimes multiple times a day, to almost never would make anyone raise questions.

Just over a year from the night in which Thomas was humiliated and went down and managed to give Hannah her first orgasm not brought on by herself, let alone multiples, Hannah would receive her last orgasm from Thomas.

Hannah did not know it would be the last, but she had realized that over the past few months she was always the one initiating. Even though he was always able to bring her to orgasm, she could tell that Thomas seemed to be on autopilot. Wanting to see if Thomas would ever take charge, she decided to no longer initiate sex and wait for him to make a move.

After 6 months of waiting, Hannah became paranoid. She begun wearing suggestive clothing, and even walking into the living room naked after a shower to ask a question. Thomas just looked over, eyebrow cocked at seeing her naked, and answered her questions before turning back to the TV.

Feeling like nothing was working, Hannah hired a private detective to follow Thomas. She figured he had to be hiding something, and was positive he it was another woman.

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After a month of tailing him, the detective met up and told Hannah flatly, "Thomas lives one of the most boring lives I have ever been paid to track. He goes to the gym, then to work, and then home. I talked to the front desk kid at the gym and he said that Thomas comes to the gym 5 days a week, lifts some weights, either runs on the treadmill or rides a stationary bike, takes a quick shower, and then leaves practically routine enough to set your watch to.

"His work also seems like one of the most mind numbing jobs. From what I was able to glean via coworkers, everyone just saw Thomas as a glorified secretary. They knew he was the son of the CEO, and if his dad was out of the office they would drop off files or whatever to him to make sure his dad got them.

"Monitoring his work behavior, he literally gets paid to browse the internet and nap. His work has a very sophisticated firewall, so I was not able to monitor any of the traffic, but I would assume he was not looking at anything aside from a well curated list of approved sites with zero social media allowed let alone any porn, dating, or forums.

"You paid me extra to watch him 24/7 the week you were out of town. During that week he only left the house twice outside of the activities previously mentioned. First was to go to the grocery store, and the second was probably the most scandalous, he got ice cream which looked like a single scoop of vanilla. The sad part was that it wasn't even in a cone, just a cup.

"He never left to hang out with friends or do anything else social like go to a bar. Also, speaking of friends, and I am including any acquaintance in that statement, the only time anyone came to the house was when you had people over the other night, but you were home with him."

"Yeah, that was a new secretary I hired with her husband. I thought she was very attractive and I wanted to see his reaction. I feel stupid for being annoyed at this, but we just had dinner, played some board games, he was completely cordial, and he didn't even give her so much as a lingering look," responded Hannah noticeably flustered.

The detective continues, "I tapped into your internet and it collected any url visited. There was some traffic, but it appeared he only goes on to check email, look at a handful of sports news sights, and look on Reddit. His Reddit account is pretty boring, he is subscribed to a number of front page usuals. The only online shopping I saw that wasn't basic home goods that raised suspicion was the purchase of a corded vibrating wand that came with multiple "sexual aid" attachments."

Hannah's face turned bright red, "oh, um, well...I made that purchase."

"Well I am sorry I could not find something, but unless he has some secret underground tunnel for his rendezvous to use, I am very certain in saying that Thomas is not having an affair, let alone even doing anything nefarious."

Coming back home from "lunch with the girls," Hannah could not help but look at Thomas and know something was going on. She looked at Thomas who gave her a soft at her return home before turning his attention back to the soccer match. She scanned him over a 1000 times as if there was some clue she was overlooking that would expose everything.

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It was not cheating that Thomas keeping a secret. It was a discovery about himself.

After months of so much sex and so much of his cum lapped out of Hannah, it became more and more apparent that it was his love of cum that kept their sex life active for as long as it did.

Looking up how normal it was for guys to eat their cum is what sent Thomas on a new path. One that when he started heading down, he started to loose any interest in sex, especially when he was completely satisfied cumming manually and eating it that way.

Thomas was no stranger to porn with amateur, anal, and more recently creampie porn. There was the occasional video that would cross categories that may cross his path that delved into what he described as risque or deviant, those categories were never really entered willingly. That is until he was specifically pointed there by content found on reddit.

He felt an awakening as he found out about femdom where women were forcing guys to eat their own cum. His favorite being when they would position their legs in the air and aim the cock so it would be unavoidable. Whenever he took a shower, he would usually prop himself up against the door as he had seen and cum all over his face. Thomas would then stand up and look in the mirror covered in his spunk before gathering it up and swallowing every bit.

This progressed further and cuckolding became a new favorite. He had seen some before, but instead of the usual husband just watching his wife get fucked, the wife got off by watching her husband sucking the cock of her bull. Seeing this pathetic man being forced to do so and then getting to gulp down cum really turned Thomas on.

The more videos he watched, the more he kept seeing these men being forced into chastity for having a worthless penis. Sometimes they would also be forced to dress up like a girl and then called a sissy. This dressup aspect really changed something in Thomas.

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As Thomas started doing more and more fantasizing, his want to fulfill these desires and make them a reality became an ever growing want. He saw his opportunity when he was sent across the country to a convention in place of his father. The convention was available online, but Thomas volunteered as he saw the perfect opportunity to experiment without worry of being discovered by anyone, especially Hannah.

To prepare for his trip, Thomas pilfered a number of Hannah's clothes while doing laundry and cleaning their bedroom over a couple weeks. Being a tall athlete herself, Hannah's measurements were not that far off from his. The only thing that Thomas knew he lacked were the breasts to fill out her bra so he packed an extra pair of socks.

Along with Hannah's clothes and underwear, the last item he knew was available to him at home was a long blonde wig. He had used it for a costume when Hannah and him attended an 80s themed party and they went as a hair metal duo.

Always scared of using Hannah's makeup after she blew up at him when he dropped a compact one time, so he purchased a small travelers makeup case at the airport that had a "nude" cream foundation, greenish brown eye shadow, black eye liner, black mascara, and bright red lipstick.

On his way to the hotel, Thomas picked up a pair of 4" chunky black heels he managed to find at a local second hand store near the convention center. The clerk laughed and said they were the perfect topper to finish off a costume and saying those shoes have been purchased and resold back to the store many times around Halloween. The clerk trailed off a little thinking that it was only August but forgot about that when he looked back and Thomas was already carrying his purchase out the door.

Putting it all together the second he bolted the hotel rooms door, Thomas felt extremely sexy. For the first time he felt a sense of comfort and that made him feel confident. He also really liked the way when he puffed his chest out to make his breasts stand out more and how the heels made his calves look so toned and accentuated his ass.

Thomas looked up places to go and he figured an adult shop would be good, and he found one 30 minutes away that showed low to no customers this time of night during a week day. Taking off the heels to drive, Thomas's stomach churned with excitement at the idea of being in public. Every time he had to stop at a light, his heart rate would go up thinking someone would see and somehow cause a scene yet excited him and kept having to tuck his penis back to keep it from tenting the dress.

Pulling up to the shop and seeing just one other car parked, he felt a sense of relief because it probably meant only one employee was working and that was it inside the store.

Thomas put on his heels and started making his way to the front door. Just a few steps in and he realized that heels are extremely uncomfortable. Powering through the burning in his calves and cramped toes, Thomas walked to front door thinking he was strutting with the elegance. Anyone else looking would be reminded of a giraffe taking its first steps with his knees akimbo and a stride that would make a police question his sobriety.

Hearing the chime, the guy behind the counter didn't even raise his eyes from the book he was reading while saying in a monotone voice, "welcome to the den of pleasure, ask me any tantalizing questions you may have, otherwise have fun exploring the wild side." He also lazily waved his arm in the air before it went back down to turn the page.

Thomas tried to keep his balance as he made his way through the small store. Even though the store was not much bigger than his hotel room, he had to stop multiple times just to let his feet rest.

Going out dressed up was the main goal, but he also wanted to get something to fill his hole like the sissies being forced to plug their holes to make it loose enough to take the wife's lover's big cock.

Just as Thomas was thinking of cock, he saw something that made his hole pucker. In the middle of the store was a raised pedestal topped with a glass case. In the case was a huge pink dildo that looked more like a deadly weapon. As Thomas eyed the monolith, he saw a piece of paper that one of the employees had drawn up like a plaque that read, "DO YOU THINK YOUR HOLE IS GREEDY ENOUGH TO TAME THIS PINK MONSTER. ARE YOU WILLING TO TAKE THE GREAT AMERICAN CHALLENGE?"

Averting his eyes from the semi translucent pink monstrosity, Thomas began looking at the more reasonable dildos. He picked up a realistic looking dildo with balls and a suction cup. On the packaging it said, new life like skin texture will make you think it is the real thing. It was maybe 6 inches long and pretty slim and the packaging labeled it as average size. Thinking about his penis, he knew it didn't not even compare.

Next he looked at the plugs and like the big pink monolith in the middle of the store, most of these plugs made his sphincter clench. At the end of the row, he found one that was just a little bigger around than the dildo at 1.5 inches in diameter and 3 inches long.

Dildo and plug in hand, Thomas moved by the tiny bondage section. He saw some gags, floggers, and various restraints and ropes, but something else caught his eye. A metal chastity cage. Thinking on the cuckolding videos and seeing the guys forced to one of these, he felt his own penis strain as he clenched his thighs together to try and keep it tucked.

Embarrassed and thinking it would ruin his perfect disguise, he passed it up and grabbed a bottle of jelly lube and made his way to the counter feeling his heart race faster with every step. When he placed the items on the counter, the employee finally looked up and the immediate look of surprise on his face made Thomas's self-assured feminine appearance shatter and instantly knew that he was just like a boy in a dress.

"Oh, hey man...I mean mam, those are some good items you picked up. I-is there anything else?"

Too embarrassed to speak, Thomas just shook his head no as the items were being rung up.

"Very well, that will be $65.38, will it be cash or card?"

The look of panic must have shown through, but Thomas just realized he should have brought cash. Reaching into the stuffed bra, he pulled out his credit card and handed it over.

The employee looked at the card then up before saying, "um Tho...Miss Hendricks, sorry, but store policy requires me to see an ID with a credit card."

Turning bright red, Thomas again dug into the bra and withdrew his drivers license.

Looking at the ID and then back at Thomas, he smiled and then proceeded with the transaction. As he was bagging up the items and handing it over he said, "I'm sorry, but did you lose a bet or something?"

Thomas could feel his face turn even more red as the heat spread throughout until even his ears started feeling hot. He quickly grabbed his items and tried to walk as fast as possible but each step hurt and made the 10 foot walk seem like 100 yards. Just as Thomas made it to the door he could hear the guy laughing and pretty sure the sound of a camera shutter.

Now fueled by embarrassment, Thomas ran as fast as he could in the heels no longer caring how much it made his feet hurt. He almost made it to the rental car when his right ankle flopped to the side and he fell forward onto the asphalt. Laying there for a bit on the verge of tears. As he started to get back up Thomas let out a shriek as a hand touched his shoulder trying to help him up.

It was the employee who was extending his hand out to him while saying, "hey man, I am extremely sorry. I really did not mean shame you like that. Hell, selling fake cocks and porn is my business. It's just, your get up really took me by surprise," the guy paused seeing how dejected Thomas looked.

Taking a deep breath he continued, "I mean, if you this is who you really are and not just trying to get your jollies off by going into public, I would really suggest looking up some tutorials or something. Remember, clothing really makes the girl, so may I suggest some that better suit your," he gestures in a mock hourglass shape, "figure. Also, maybe don't go for heels right away, work your way up if that is what you want to wear."

Thomas now on his feet, not realizing it in the store but the employee must have been on a raised platform behind the counter as he was now looking down on the guy. Even still he couldn't look him in the face, and he wiped the tears rolling down his cheeks and seeing large smudges of off white cream colored foundation on his hand obviously not a shade remotely close to his light brown tanned complexion.

"Hey man...sorry, I mean miss, everyone starts some, where...," he trailed off before giving Thomas a pat on the shoulder and then quickly turning around and walking back to the store.

Embarrassed by the whole situation, Thomas was oblivious to the fact that his penis was as hard as it gets and even for how small it was, it was creating a noticeable tent in the front of his ill fitting outfit.

Ripping off the heels and tossing them into the back seat, Thomas drove back to the hotel in such a hurry that the drive itself is nothing but a blur. He kept replaying the whole situation over and over in his mind, and each time the situation grew bigger and bigger to the point he was imagining an entire crowded store all laughing at him.

Grabbing his purchased items and quickly running into the room just thinking that everyone in the hotel was looking out their windows pointing and laughing. He slammed the door behind him and looked through the peep-hole to make sure the crowd he had imagined weren't in fact gathering with pitchforks outside his door. When he saw the coast was clear, he turned around and looked at his empty room and began to slide his back against the door feeling overcome by emotions.

Seeing mixtures of black mascara and cream foundation dripping onto the shelf of his sock padded boobs in Hannah's dress just made him feel even worse. Getting up to go to the bathroom, he felt the pain of his sprained ankle and the road rash on his knees making him yelp at first and wince with every step.

Standing in front of the mirror, it was not the runny smudged makeup or the now obviously ill fitting nature of the dress Thomas saw. Looking down and over the misshapen filled bra, he saw the tenting in the dress with a very noticeable wet spot.

Looking at it in awe of how much he had been leaking pre-cum to create such a wet spot. Lifting the dress off and pulling the very moist panties to the side, a strand of pre-cum oozes out creating an unbroken clear thread to the floor.

Looking up into the mirror seeing himself no longer on the excited high of putting on girls clothes, but how the employee actually saw him, a boy in a dress with makeup that even when it was first applied looked like it was done by a toddler doing their first finger painting.

A wave of humiliation washed over Thomas as he reached for his penis that he could now feel pulsating in the open air and knew he was harder than he had even known it to be. Thomas began thinking of the store clerk laughing and taking a picture of him as he gripped his penis. Just touching it was enough before a blast of energy like lightning burst through his body.

The wave of pleasure combined with the humiliation being replayed in his mind exploded into an orgasm that made his vision go blank and fall back against the wall. The long thick ropes of cum shooting forth across the bathroom would have looked like her was be pushed back by a cum canon. Thomas's mind was nothing but a fireworks display setting everything off while his body went from fully flexed to limp and crumpled to the tile floor.

To be continued