His First Time

Hello everyone. This is another (attempt of a) one shot. I hope you enjoy it as much as I did and take care of yourselves and avoid the Coronapocalypse™. Edited by FelixRyder.

Frank's moans of pleasure broke the silence of the room. The petite young man had his legs in the air, spread apart, while a beautiful blonde woman held them up by the ankles. Frank laid on his back on that bed and was enjoying a lot as he had never done in his short life. His eyes looked down to his abdomen, which rose and fell rapidly with his erratic breathing. His tender and flaccid micropenis rested on his own tiny testicles, dripping a bit of pre-cum.

His ass was completely filled by the huge dick of that woman, who moved her hips in a constant and intoxicating pace. The woman smiled triumphantly and looked at her partner's panting and excited face. But to know exactly how Frank got into that situation of being drilled by a transsexual woman we have to go back in time to a month ago.

"Congratulations, Frank. Now you're 19."

Frank Smith was finally able to blow out the candles on his cake; he was officially a year older. He was at home with his parents and other relatives who had come to celebrate, as well as a few friends. Frank was a short, white boy, around 5,2" tall and his physical build had always been slim. His short brown hair and his brown eyes were a magnet for girls, who saw in him the perfect boy. Although a few would say that Frank had rather a graceful figure and was somewhat feminine in some way, like his bubble round ass, but the kid was not bothered by what others might believe.

Hugged by his parents, he later found himself surrounded by his uncles and cousins. Lastly, Carl and Arthur, his best friends; somewhat similar to him but more hung. Carl had jet black hair and bushy eyebrows and Arthur had long brown hair and an earring in his right ear. While his mother was serving the cake and his father was reliving old childhood stories of "little Frankie", Frank went out to the backyard accompanied by his faithful mates, since he did not want his friends to laugh at hearing several uncomfortable episodes from when he was a child. The night was a bit cold and Arthur lit a cigarette to warm himself.

"Come on man, turn that off," Carl muttered, annoyed.

"Leave him alone, the poor man resisted a long time inside the house," Frank acknowledged.

"Yes Carl, this is a free world and I can do whatever I want," Arthur commented as he smoked his cigarette.

Carl snorted, upset, but Frank just looked in front of him, absorbed by those words. Now that he was 19, it was finally time to do something crazy, Frank thought as a slight smile appeared on his beardless face. He could hear the voices of his friends next to him but he was not paying attention to them, wondering what things he could do with complete freedom, perhaps doing something about his little problem.

Well, the first thing would be to lose virginity, Frank thought.

And that idea made him nervous. The subject of sexuality was something that made him very excited but he knew that he couldn't be a stud in the best style of the porn actors he saw in some videos. Very soon Frank realized something that did not worry him much when he was a teenager: his dick was way too small than average size. And if some actors, with at least 6 inches long and decent thickness, Frank's "cock" was just about 3 inches and all hard.

Last year, after seeing enough videos, that insecurity of having a very small penis invaded him but he preferred enjoying lonely times rather than being embarrassed or humiliated in front of a chick because of his micropenis. One day while he was browsing the Internet in search of a video, an ad appeared on one of the pages he frequently visited that left him speechless.

A very sensual and curvy brunette woman with nice tits and ass, but she had a strange bulge under her panties... when pushed them aside, she revealed a fat and flaccid cock. Frank was victim of coughs and stupefaction.

"What the fuck...?" Frank exclaimed softly, his eyes looking at the ad that appeared on the page.

The boy still did not get out of his amazement and shock but he did not close the pop-up ad, while he watched as the woman jerking off and her cock reached a size unimaginable for Frank, at least 8 inches and very thick. He had never seen a transsexual and not so beautiful like that woman; he always imagined them as crossdressers or something similar.

"Damn, she is so beautiful... if I saw her on the streets I wouldn't be able to know that she has a dick," Frank thought without taking off his eyes at the sensual moves the woman was making and his eyes couldn't stop staring at that perfect dick.

That thought terrified him a little, he was straight... but looking at his lap his own cock was stiff as a wooden rod, to his surprise. Hesitating a bit, Frank put his hand on his cock and began to jerk off slowly at the same pace as the woman was, then faster and in less than 2 minutes a jet of cum escaped from his cock and ended on the keyboard. Another two shots ended in his abdomen; when he finished, Frank could not believe what he had done! He had jerked himself looking at a well-endowed and beautiful transsexual.

"Frank, Frank? Wake up dude," Carl pushed him as he returned to the present.

"Eh, what happened?" Frank said after being interrupted.

"Man, looks like you're somewhere else. I have asked you three times, what will you do next week? We must plan something big," Carl repeated impatiently.

"Bro, I don't know..." Frank replied to his friend.

Actually, Frank was lying. Of course he knew what he would do, but he didn't want to share his most secret fantasy with his friends because he was afraid they wouldn't understand him. He was sure they could judge him for what he felt that night, a year ago; when he was watching porn and that ad appeared in the lower corner of his monitor. Since that night, an unknown and unusual desire for transsexual women awoke inside him and at least twice a day he jerked his little meat, fantasizing about a beautiful girl with a cock.

Soon, the watched videos were of real action. At first he only watched pretty girls being rammed hard, but everything changed when he saw his first top trans woman. And Frank knew in that moment, that what he wanted the most was to taste a transsexual girl with a good cock... and top. Considering that he would probably not be able to please a girl properly, it was the only viable alternative for him and one that caused him the most forbidden excitement.

In that moment, Peter, Frank's grandfather, came out to the patio where the three friends were.

"How are you guys, Frank... could you come over for a second?" Peter said.

Frank, dazed, met his grandfather away from his friends. "Why does everyone insist on talking to me when I'm thinking," Frank thought while walking.

"Once again, congratulations. I would like to give you a small gift, I know it will be useful," Grandpa said and taking an envelope, he handed it to his grandson.

"What is this?" Frank asked with an intrigued voice.

"Just open it, I don't want to ruin your surprise," Peter insisted.

The young man suspiciously broke the seal on the envelope. He knew very well that his grandfather, despite his age, was still one of those pesky jokers and that is why he doubted about the content of the envelope. To his delight, there was a good amount of cash inside the envelope.

Taking out the money, he looked at him in disbelief as his grandfather smiled at him.

"Hey, this isn't a joke, is it?" Frank muttered skeptically.

"Of course not, it's my present to my favorite grandson," Grandpa admitted.

"You mean the only one..." Frank said with some irony.

"And that's why you are my favorite. 2000 bucks for you, spend it as you wish," Grandpa said.

"2000? Wow... well, thank you Grandpa, I did not expect this. I thought you were going to prank me or something like that," the boy admitted, putting the money in his pocket.

"Well, at first I thought about doing it. But it's better this way, just one thing: don't spend it with those over there..." the grandfather advised in a low voice as he looked at Carl and Arthur, who were fighting because Arthur was still smoking.

"Sure, you don't have to tell me. Again, thanks for this," Frank said.

After a brief handshake and a kind of half hug, Grandpa Peter returned inside, leaving Frank with his friends. Once he returned next to his friends, they made a space for him and he stood in the middle of them.

"What did he tell you?" Arthur asked.

"Oh nothing. You know, the typical grandparent thing," Frank replied.

One by one all of them left the house. Frank's parents went up to sleep and the young man was alone in his room, naked and massaging his little piece of meat between his thumb and middle finger. He kept thinking about how a thick cock would feel in his tight, virgin ass, sinking deep inside him.

The only bad thing was, he didn't know a trans girl to fulfill his fantasy. And he did not know of anyone who could recommend one, but in that moment Frank realized that everything was possible. With the money given by his grandfather it would be possible to pay for a lewd trans woman and her pole.

Leaving his bed, he sat down in front of the computer and turned it on. Soon he started browsing in different flirting pages of transsexual escorts in the city. As he looked at the ads and photos, Frank couldn't help at the sight of all those women, their curves, those perfect asses and what to say about those stiff cocks ready to get into action.

There were so many, and each one more beautiful than the other that Frank couldn't decide on a particular ad. Until he finally found the one.

"Luana, the most sensual girl from Sao Paulo, 25 years old. Fluent Portuguese, Spanish and English, affectionate, educated. I have something between my legs for you to enjoy, 8'6 inches just for you. I love being active and dominant, so if you have courage and want to try something new, call me or text me and you will not regret it," Frank read, accompanied by a series of photos of a beautiful blonde with green eyes, big tits, scandalous curves and a cock that made his jaw drop.

"Hmm... we have a winner..." Frank thought as he licked his lips lustfully.

By clicking on Luana's profile, it gave the option to "See Number" and after adding it to his WhatsApp, he stared at the screen for a while, without idea of what to write or if profile was fake. Taking a deep breath Frank encouraged himself and put his fingers into action.

"Hi Luana, my name is Frank and I just saw your ad online and I would like to book an appointment," Frank wrote.

He waited a few minutes for Luana's reply and as he did so, he laid down on his bed once more staring at his phone, his heart beating violently and wondering if he could find what he was looking for.

At that moment, his mobile phone rang, indicating that he had a WhatsApp message. Nervous and invaded by tremor, Frank picked up his phone and opened the unread message.

"Hello Frank, thanks for replying to my ad and I am very happy that you have contacted me. As you may have read in my ad, I like to be active exclusively, if you don't have a problem with that then I'm the ideal woman for YOU, xoxo," Luana replied.

Frank's heart almost came out of his chest when he saw that she had answered him, in addition to feeling a slight spasm in his ass when he read Luana's last words. She was definitely the one, but he had to make sure it was the same woman from the photos.

"Yes, I have no problem with it, that's why I decided to contact you," Frank wrote.

Luana's response didn't take so long and anxiety began to grow in Frank.

"Perfect! I assure you, you won't regret it, Frank. At what time do you want to have your date? It can be tonight, only one hour of anticipation," she detailed.

"Tonight is difficult for me, but if you can, how about in two days?" the young man proposed.

Luana took a little longer to answer but it would be worth the short suspense.

"I don't usually make appointments with days of anticipation, but I'll make an exception for you. In the meantime, I will send you some of my pictures so you can fulfill your fantasies," Luana wrote and sent him some photos of her in lingerie, as well as a short video of about thirty seconds.

Unable to believe his good luck, Frank spent hours jerking off as hard as he could. Luana was very hot, making honor of her Brazilian descent because she had a great body and nice thick curves, Frank thought as he shook his small but rock hard cock looking at her pictures and the video.

The next morning he woke up suddenly. Indeed, he had fallen asleep naked while jerking off and he could even notice small white spots on his abdomen, the silent remains of a good night out thanks to Luana. Putting on a green shirt and shorts, he went to the kitchen and made his breakfast.

His mother found him when he had already eaten almost all his breakfast and kissing his cheek, she sat down to eat.

"If you go out today, could you buy some stuff? I'll give you a list to remember the items," his mother said.

"Sure, no problem. I'll take a shower and will be ready in 20 minutes," Frank replied.

Once showered and ready, Frank took his money given by Grandpa Peter and went downstairs and waited for his mother; she appeared a couple minutes later with a paper.

"If you can have them all before 3 o'clock, that'd be great," his mother said as Frank checked the list.

"I'll do what I can. I also have some things to do but yes, I hope to be back before 3," he mumbled.

Heading towards the main avenue of the area, which was about 200 meters from his home, Frank waited a few minutes until the Uber he requested arrived before leaving home. Once downtown, the young man walked the main boulevard buying the different items on his mother's list and when he finished he went to a narrow alley that led the way to the Red-light.

Entering into the first sex shop he saw, with some shyness he looked at the merchandise, the store had everything; from costumes to lubricant. Taking one, then he began to snoop in search of a dildo or butt-plug, but only the clerk, a petite red-haired woman in her thirties, was watching him with a sneaky smile. After searching for some minutes, Frank was still unsure if buying a dildo or not to prepare his asshole the night before the big day, when a soft voice from behind surprised him.

"Do you need help?" the clerk asked with a kind look in her face, trying to contain her laugh.

"Uh... I was... I was just..."

"Don't worry. You're not the first one that comes here to the store looking for lube and a good dildo," she assured and put her hand on his shoulder.

"Well... the truth is..." he stammered again.

"It's fine, I imagine it will be your first time and I have the right toy for you," the woman said as she took a dildo about 7 inches long and about 3 inches of girth.

Frank swallowed nervously when she looked at him and the woman could no longer contain her laugh.

"It's just a cute little toy. I can tell you that you'll find bigger and thicker cocks than this little friend over here, if you are lucky enough. Before trying it, you can practice with your fingers and then with lubricant, relax your body and it will fit," the clerk advised.

"Will it hurt that much?" Frank asked with childish curiosity.

"Will it hurt? Well, it always hurts, kid... it's about your ass that we're talking about," she replied with a laugh and then added, "It may hurt more or less, depending on which position. I would recommend you to lay on your bed with your legs separated, it will be very easy and... pleasant after a while."

Frank felt more comfortable with that tip.

"T-thank you... very much," he stuttered; he couldn't avoid feeling nervous but he was now sure of what he wanted to do.

"That's what we are for, to help the client. Believe me, no dildo compares to a good cock, but I hope you enjoy this a lot," the woman wished and they went to the cash register.

After paying for the items he carried in a very discreet bag, Frank returned home where his mother waited anxiously for him. Giving to her the bag with her stuff, he locked himself in his room, ready to put into practice what the woman in the store had commented.

Ditching his clothes, he was naked and anxious. Laying on his back on the bed, he grabbed the bottle of lubricant and smeared a good amount on his hand and then passed it between his fingers so that they were all well lubricated and finally, he began to shyly pass them through his sphincter.

The touch of his lubricated fingers against his rear crack felt great and he began to massage his anus, relaxing the sphincter as much as he could to proceed. First he slowly inserted the tip of his finger, and instinctively his asshole reacted to the intrusion by preventing it from sinking further.

Frank massaged it again and when he felt the muscle relaxed he repeated the action. This time it entered just over half and held it still, waiting for his virgin hole to adjust. A slight tingling spread throughout his body and his small cock also reacted by getting very hard. The young man shoved the rest of his finger and a slight moan of ecstasy escaped out of his mouth.

After several minutes with his finger inside his ass, Frank dared to put it in and out slowly. The intoxicating sensation that gesture caused in him was beyond imagination and pre-cum began to leak out, so the boy continued stretching his ass. As time passed on and he felt used to the presence of his sneaky finger, he thought about adding a second finger. Pausing and moving carefully, after a couple of attempts he managed to get two fingers up his ass.

Feeling the greater thickness invading his rear, Frank took several deep breaths to get used to it. But just like his first incursion, his ass not only enjoyed being penetrated, but it begged for more.

"Well, it's your turn now..." he said quietly looking at the dildo he had bought.

Using a significant amount of lubricant, Frank lubed the dildo and also placed a little more on his ass in case it was necessary so the dildo would break in easier. With the tip of the dildo, he stimulated his sphincter and applying some pressure, he pushed in the tip and immediately pulled it out again. That sensation of a foreign object ready to penetrate him charmed him and he ended up shoving more than half of the dildo into his hungry ass.

For the first time in his life he felt very full and tried to breathe calmly and spread his legs as wide as possible to facilitate the entry of his toy. The reflex action of his body told him that he should expel that object out of his ass as soon as possible but the horny young man sought to relax a little more and get used to the size of the dildo.

Once the goal was reached, Frank began to move the dildo slowly in and out, trying to shove it as deep as he could, almost ending up pulling it out and then pushing it back inside his asshole. Liking the feeling of a long dildo drilling his ass, it was wonderful and, as he rolled up his eyes, he increased the speed of his hand. That lasted more than 20 minutes in which Frank shot his load a couple times on his belly and chest without needing to jerk off. The continuous anal pulsations when stimulating his prostate sent waves of pleasure throughout his body, especially to his cock and clouding his senses so that he had to cover his mouth with his fist to avoid moaning outrageously.

After showering and dressing, the pulsations in his ass continued for a while, his mind enjoying the incredible sensations he discovered. He also had to hide his strange way of walking in front of his parents but they did not notice anything odd in their son, who devoured dinner like he was possessed, just to be alone in his room and repeat the experience.