PrincessBoy Diaries

Palm Springs Getaway With Daddy

“Pick you up in 15 minutes”. It was a text from daddy; the text his boy princess had been waiting for all day. Daddy had surprised him last night by telling him they were going to Palm Springs for a weekend getaway. He had been working long hours to finish a project  so they were both looking forward to quality time together. Daddy told him they would have to make an appearance at a cocktail party for work on Sunday, but the rest of the time was just for themselves. Princess had spent all day packing his bags, though he knew daddy would surprise him with gifts in Palm Springs. Daddy always liked to surprise his princess with gifts and always picked out outfits that made him look his best. 

Daddy and princess enjoyed the drive to Palm Springs and arrived at their clothing-optional resort in the mid-afternoon. As they walked to their room, they both enjoyed looking at the variety of men around the pool. Princess knew that daddy would be showing him off before long and he started to get excited. 

Though they could be naked, daddy enjoyed a slutty thong tanline on his princess. Daddy put on a tight swim brief that made his package stand out, and made princess smile. He then pulled out a small paper bag for princess: the first of many gifts. Princess opened the bag and found a shiny pink thong. He stripped off his clothes and put on the thong. The strap was very skimpy and the suit was designed to show off princesses dick whenever he got hard. Daddy began to rub and lightly spank princesses butt, he knew that would do the trick to make him rock hard. 

Daddy opened the door and they made a stroll around the pool. He loved parading his princess around, especially in a tiny thong. The men all began to smile and wave as they walked past. One of the naked men started to get fully erect. Daddy looked at him and gave him a smile. 

Once seated, daddy began to rub tanning lotion all over his princess. Men continued to stare in their direction and daddy loved every moment of it. Daddy and princess snuggled in lounge chairs, talking and laughing. Daddy would occasionally slide his fingers under princesses thong strap and finger his boy pussy to make him erect. Once princess began to precum, daddy would make him stand up and walk around the pool for all the men to see. 

After a few hours in the sun, daddy whispered in princesses ear, “let’s go shower”. They gathered their belongings and went to the outdoor shower. They began to hug, kiss, and rub each other as the water fell down on them. Daddy grabbed princesses butt cheeks and began to massage them. Then he reached his hands up princesses back to his head and motioned him down. Princess knew exactly what to do. He got on his knees and began to suck on daddy’s rock hard cock. They had been teasing each other all afternoon and both were happy to be playing in the shower. Daddy made princess stand and turn around, facing away from him. He grabbed princesses hips and pulled the shiny pink thong off of his wet body. 

Daddy began pressing his hard cock up against princesses butt. The water continued showering down on them. He looked over and saw two men watching. They were rock hard and stroking. It made daddy even harder. He slapped his hard cock against princesses boy pussy and slowly pushed it inside. Princess began to moan. He had been waiting all day to feel daddy inside of him. He craved daddy’s cum and could not wait to receive a big load. Daddy began slowly grinding in and out of princesses pussy. He kept looking at the men who were watching and the more they jerked, the faster daddy began to fuck his princess. Before long, daddy and the onlookers were stroking and fucking in unison. Princess continued to moan until he couldn’t take it anymore. He began to beg, “Breed me daddy! Give me that load! I need your cum deep inside my pussy”. Daddy couldn’t contain himself, neither could the onlookers. One of the onlookers began to cum, which made daddy do the same. He exploded deep inside his princesses pussy. He let out a loud, deep, manly moan as he exploded, which made princess explode as well.  Daddy turned off the water, walked over to his bag, and pulled out a metal butt plug with a pink jeweled end. He walked over to princess and shoved it inside him, to keep his load inside princess throughout the evening. 

Daddy and princess returned to their room for a little pre-dinner nap. When they awoke, daddy pulled out another bag for his princess. This time it was a larger bag. Inside was a black satin thong bodysuit and bright, tight pink shorts. Daddy told princess to put on the bodysuit and shorts. He also gave princess matching long, pink socks to wear with black high tops. Princess put on the outfit and departed with daddy. 

Daddy paraded his princess around as they walked to dinner. All the men dining outdoors turned and watched as they walked hand in hand. After being seated, daddy began to kiss princesses neck. Then he slowly ran his hand up the bottom of princesses shorts, slipped past the thong, and started to rub his pussy. Princess blushed and tried not to get hard. This continued throughout dinner so much that princess leaked through his bodysuit and shorts. He was embarrassed, but daddy reassured him that it was ok and that he enjoyed seeing how excited he made his princess. 

After dinner, they walked to a nearby gay bar and ordered drinks. Princess was ready to give daddy a taste of his own medicine. He sat on daddy’s lap and began rubbing up against his dick. Princess could feel daddy growing bigger and bigger. He stood up and began rubbing daddy’s bulge. Daddy told princess that he was starting to leak. Princess hated daddy’s cum going to waste, so he lead him to a restroom stall. He got on his knees and pulled out daddy’s dick. The precum was shining on the top of daddy’s perfect dick head. Princess couldn’t resist that sweet daddy cum so he wrapped his lips around it and began to suck. Daddy grabbed the back of princesses head and forced his dick deeper into his mouth. The stall filled with sounds of princess slurping and sucking daddy’s perfect dick as daddy began to cheer on his princess. “That’s it, keep going princess, you’re such a good cocksucker. Get daddies seed. I love seeing my princess on her knees.” Princess kept sucking and looking up at daddy with eager cum hungry eyes. Daddy couldn’t take it anymore and began shooting load after load of thick, creamy cum. Princess swallowed every drop and then pulled daddies dick out and gave him a big smile. Daddy and princess were both surprised when one final shot came out of his dick, right onto princesses pretty face. He put his dick back into his briefs, zipped up his shorts, and helped princess up from the floor. Princess knew daddy would make him wear that shot of cum on his face all night, and that’s exactly what he did. 

Saturday 

Daddy and princess spent the next day in the sun. Showing off to all the men by the pool. When it came time to dress for dinner, daddy had another gift bag for his princess. This time it was a bright red thong, long thin white socks, along with a white crop top that fell right below princesses pecs. Princess looked further for the rest of the outfit, but the bag was empty. He looked at daddy with a confused look. Daddy smiled and pulled out a red, black, and white plaid skirt. Princess smiled and quickly took the skirt from daddy and began to put it on in front of the mirror. Daddy walked over and helped princess zip the skirt. They stood there looking in the mirror. Daddy reached up the skirt and began to caress princesses butt cheeks. 

After a moment, the smile disappeared from princesses face. Daddy asked what was wrong. “I can’t wear this out tonight. What will people think?”  Daddy hugged his princess and reassured him that everything would be ok. His princess was beautiful and daddy wanted to show him off in a pretty, sexy outfit. Princess was reluctant but trusted daddy’s judgement. 

Princess and daddy strolled down the street. Daddy knew princess was nervous, so he kept his arm wrapped around him as they walked. The more they walked, the more princess began to feel comfortable and confident. He felt safe and secure with daddy’s arms around his waist. A feeling that continued throughout dinner. 

After dinner, daddy and princess went out for drinks. At the bar, daddy couldn’t keep his hands off of princesses butt. They stood at the bar and daddy reached up and grabbed one of princesses cheeks.  The motion made the back of the skirt lift and princesses thonged butt was on display for all the men at the bar. Princess got so turned on that he couldn’t contain his erection. The bulge of his thong began to grow more and pop out from under the skirt. He was on full display for all the men. Daddy was enjoying showing off his princess, but his cock was growing hard and he knew princess needed to take care of it. 

Daddy and princess went back to their resort. As they walked by the pool, daddy told princess to strip and get on all fours. Princess did as daddy said. Just as he got on all fours, three men returned to the resort. They looked at princess with his pussy exposed. The men looked over at daddy, he smiled and motioned for them to come over. The men walked over and he told them to rub princesses butt. They gladly reached down and began rubbing princesses butt. One stood up, stripped, and walked over to look princess in the eyes. Princess looked up at the man and his long, hard, cock. The man smiled and princess opened his mouth and began to suck the man. The other two men were still grabbing princesses butt. One of them spread his cheeks and began to bury his face deep inside princesses pussy. The other man stood up next to daddy, both were stroking their cocks as they watched princesses suck and get rimmed. 

Princess continued to suck one man as the rimmer decided to slide his dick deep inside princesses pussy. The two men using princesses holes were high-fiving as princess took both of their dicks. The man who was getting sucked, started to moan. Princess knew he was close to cunning. Daddy told the man to shoot his load down princesses throat, and the man did exactly as he said. Seeing that made the man fucking princess explode deep in his pussy. Daddy and the third man had been jerking the entire time. They shot their loads on princesses pussy and daddy pushed the loads inside princess with his dick. The men all smiled and thanked daddy and princess. Princess was wore out, so daddy took him back to the room and cuddled until they fell asleep. 

Sunday

Princess was so happy from everything daddy had been doing all weekend, that he decided to bring daddy breakfast in bed the the next morning. As daddy ate, princess kept busy by sucking daddy’s morning load. Princess also arranged a couples massage so they could both relax before the cocktail party they had to attend with daddy’s boss. 

When it came time to get ready for the party, daddy had one final outfit surprise for princess. Since it was a work event, he assumed it would be a new suit. Daddy pulled out a large box. Princess opened and saw something completely unexpected, a black gown and a tiny black thong. Princess looked at daddy, who had a mischievous grin on his face. Princess though this must be a joke, but before he could say anything, daddy told him to put on the outfit. 

“Daddy, no! I can’t.”  It was one thing to go out to dinner and drinks in a tiny skirt around complete strangers, but tonight would be around daddy’s boss and coworkers and their wives. “Calm down princess” daddy said. “You’re safe with me. I wouldn’t do anything that is going to hurt you in any way.” 

Princess believed daddy, but was still scared. Daddy had never pushed him this far and it was all happening so fast in one weekend. He was loving all of the outfits and loved how sexy and feminine daddy made him feel. But he was scared that daddy might jeopardize his job. He was also worried about how everyone at the party would react. How would they treat this boy princess?  Until now it had always been an aspect of their lives that he and daddy had kept to themselves and random strangers they encountered while living out fantasies on vacation. 

Daddy hugged princess and told him to put on the thong and gown. He reminded princess they hadn’t packed anything else that would be suitable for the party and there was no time to shop. Reluctantly princess put on the thong and then slipped the gown over his head. The spaghetti straps fell into place on princesses shoulders and he looked in the mirror at the deep v-neck body attached to a long, flowing, black mesh bottom. Daddy walked up behind him and wrapped a diamond necklace around his neck. He followed it up a matching diamond bracelet and a pair of glossy black high heels. 

Daddy put out his arm to escort princess to the party. As they walked through their resort, princess began to feel nervous, but daddy continued to ease the nerves by gently hugging him and grabbing his butt. Those gentle butt rubs always put princess at ease. 

As they walked out of the resort, princess was surprised to see that daddy had arranged a limousine to transport them to the party. The driver was smiling and waiting at the car door. He opened the door and held out his hand to help princess into the car. Daddy followed and they were on their way to the party. It felt like a true fairy tale to princess. 

When they arrived at the party, daddy gave princess a hug and kiss as final encouragement. He told princess how beautiful, sexy, and amazing he was, and not to worry. They walked into the party, heads turned and everyone got quiet. Daddy’s boss walked over and shook his hand and then extended the same greeting to princess. “How do you do?” He asked. Princess replied and looked around and noticed everyone had gone back to talking and enjoying the party. 

The next few hours consisted of daddy talking with his coworkers as princess made small talk with their wives. After a few drinks, one of daddy’s coworkers says to him “Your partner looks a hell of a lot better in that dress than all our wives!”  Daddy told his coworker that he picked out the dress specifically because of the slits on the side; it gave daddy easy access to princesses boypussy.  He told the men all about the previous night and how good his pussyboy princess is at pleasing men. 

Daddy could tell the men were intrigued, so he motioned to princess to come over and join them. Princess walked over and daddy began to rub his hands up his dress and start teasing his pussy. The men watched as princess began to get hard. They had never seen a dynamic like this before. Daddy suggested they all retire to his bosses den for a while. 

In the den, daddy helped princess take off his gown. He was left standing in front of the men in only a thong, jewels, and heels. The men begin to loosen their shirts and pants. Daddy licked his finger and shoved it up princesses pussy as the men all watched. They were completely fixated by the slutty princess in front of them. 

Princess drops to his knees in front of daddy, unzips his pants, and pulls out daddys hard dick. All the men watch as princess begins to suck daddy. The men get hard and begin stripping off their clothes. As princess sucked daddy more, the men started stroking their dicks. Princess looks at the half-dozen men watching him serve his daddy. Daddy smiles at princess and motions for him to go please the men. He crawled over to the line of men and began sucking them one by one. Daddy says “if you think his mouth is amazing, wait until you try the pussy.”  

One of daddy’s coworkers walks over and begins to finger princesses pussy. He says he’s never felt anything like it before. It feels amazing. Princess moans as he fingers more and more. The man can’t stand it any longer and slowly starts to slide his hard cock into the boypussy. His eyes begin to roll in ecstasy. The other men watch and eagerly line up for their chance to try this new, sexual delicacy. Princess boypussy is so new to them, and most of their wives won’t have sex with them, so they don’t last long. One by one, they blow their loads into princesses pussy. His pussy gets so filled with cum that it starts to leak out. Daddy takes this as his cue to bust the final load deep inside his princess. The men all cheer him on as he destroys princesses pussy with his cock. Princess is moaning so loudly that the mens wives knock on the door to make sure everything is ok. The men tell them to go away, as they quickly turn back to the boypussy breeding happening in front of them. 

After daddy shoots his load, he helps princess get dressed again. The other men dress as well and all rejoin their wives at the party. At the end of the night, daddy’s boss walks princess and daddy to the door. He tells daddy that he’s impressed with how bold daddy is and that any man that bold is one he wants to work closer with. He tells daddy to take a few extra days off to spoil princess and then come back to work, in a new position. Daddy just earned himself a big promotion, with the help of his princess. 

As they walk to the car, daddy wraps his arms around his princess and thanks him for trusting him. Princess thanks daddy for the amazing time they have had in Palm Springs, and for daddy’s help in making him feel like the sexy princess he’s always wanted to be.