The Shy Boy and I

After the great very positive repercussion of the trilogy "I gave it to my son's friends" (I loved the e-mails with the compliments... keep sending), this story was forgotten on my computer. In fact, it was a draft, half by half, but after telling the episode of Gui, the shy boy of the above stories (I know you haven't read it, stop here and read it all, you will love it).
Like Gui, this also involves a young man (I'll call him Greg), who despite being in his early 20s, was very shy and sexually withdrawn. Coming from an extremely close-knit, religious family, Greg despite being very handsome and having an easy time making friends, with women was a bit, let's say, stuck.
It was Charles who told me this story during our Skype chat, and he said that his friends had noticed that Greg was having a hard time with the other girls in his class.
I asked if he wasn't gay, Charles laughed... said that Greg was just kind of stuck with the opposite sex, even, once he asked Charles and friends to introduce him to a certain "little hell" that they always frequented.
They took Greg to this place, and even introduced some girls to him, and he was excited and excited at one point, according to Charles, and he and his friends, to help out the fellow, even paid for a girl to stay with him.
Greg accepted, and went with the girl to the room, and according to Charles, although he had sex with the girl, it could be seen that he had not been fully satisfied with the program.
Greg could not explain the reason for the dissatisfaction, for friends it could just be nervousness, but after he told the story of his life, they realized that perhaps the raising of a strict family, where anything was sin, had messed with his psychological.
He needs a real woman, Charles joked.
I understood what he meant, but I refused, saying he needed a therapist, not me.
Charles said that Greg had already begun sessions with a psychologist on the recommendation of a friend, who was even more loose, but now he wanted to help his friend once again.
I said no, but Charles decided to send me a picture of them at a party, and Charles was with Greg and his friends around a pool, all in shirts, and Charles tells me who Greg was in the picture.
Greg must have been about six feet tall, brown hair, but what struck me was that the boy was kind of bulky, his muscles were quite spare, and I had already cursed Charles, saying that the boy was not the same person he was describing to me.
Charles, you said that Greg's sessions were working, that he was even going to the same gym as his friends, so his physique was healing.
I say then that the boy was on the right path, that it was just to let him live the life as he wished, but Charles tells me that he had asked for them to go back to the hell they were before.
You're the only one I trust to make him feel like a man... the girls there are cold, they want to do things quickly, take the money and leak... I don't think it's right for him.
I was thinking about it, and I said I'd answer another day, and the other morning, I was thinking about how pleasurable that intercourse with Gui had been, and even though I had taught that boy a lot of things, I had also felt a lot of pleasure and excitement in it, and even though I like to be submissive, sometimes I also like to control the situation.
I open my phone and I look at the picture of the boys again, and I visualize Greg, and my five minutes of madness took over, and I texted Charles to say okay.
A few moments later, Charles responds with three emojis.
That night, Charles and I exchanged a few texts, and I asked him if it would be okay to be in that cottage at the farmhouse hotel that we rented for that rave, and he agreed, and he was even going on the farmhouse hotel website to make a reservation, and we arranged to meet on a Saturday afternoon.
On Friday, I call Charles, and he tells me that they're already packing up and he's told Greg that they're just going to rest and enjoy the outdoors.
They arrived on Friday night and Charles had rented two cottages, one secretly in my name and another where he would stay with Greg and two other friends (who were already aware of our plan).
On Saturdays, I'd put on a really tight baby-look and a really tight bermuda, pack my suitcase, and head to the ranch hotel, which was about an hour from my hometown.
When I arrive at the site, I report to the concierge and after confirming my reservation, I drive and go to the cottage, which was the last of several, including it was further away from the penultimate by a long garden due to a large tree that stood between them and then began a vast enclosed forest.
After I get settled in, I text Charles, who responds immediately, and he says that they were in the fishing area at a newsstand drinking, and we agreed to pretend that we were meeting by chance so as not to put any pressure on Greg.
I went to the lake, and I noticed that most of the cottages were empty, including the last five (only Nicolas and his friends were in the penultimate and I in the last), which was to be expected, since it was midseason and the hotel only crowded at the end of the year and school holidays.
As I approach the kiosks, I notice Charles and his friends at the table. I walk right past them and go to the bar to get a juice, when Charles "pretending to be surprised" calls me. After the scattered excuses of "What a surprise", "I haven't seen you for a long time", "what are you doing here" ... he decides to introduce me to his friends.
All young, relaxed guys, except for Greg, who, despite being very nice, got a little shy of my presence, and I sit down with them, and we start talking randomly, and I notice that the other guys start coveting me with their eyes, and Greg would also give me crazy looks, and sometimes I'd stare at him, and he'd be shy, and he'd look away.
So Charles calls his two friends to go fishing, and he knew that they didn't even know how to fish, but it was an excuse to be alone with Greg.
I sit in front of him and I start talking to him to relax, normal conversations, and I notice that he gets more relaxed as time goes on, and he even starts telling jokes and talking about college life, and I notice that he keeps staring at my breasts.
I ask him if he doesn't want to go to the pool, shy he says "maybe" and we go to the pool.
As soon as we arrived, the pool was empty. He sits on a sun lounger. I sit next to him, raise my arms and remove my baby look, showing off the top of the bikini. I get up, unbutton my shorts and pull, showing off the thong.
His eyes sparkle, and I can tell he's eating me upside down with his eyes, and I take a sunscreen and I ask him to go over my back, and he throws it a little bit into his hands, and it starts at my shoulder, and I can tell his hands are shaking, and it goes down my arms, and I ask him to spread it over my back, and he does.
I get some suntan lotion, and I go through his belly and his chest, then his thighs and his legs, and I feel his hard cock under his bermuda, and I ask him to take off his shirt so I can go through him, and he's kind of freaked out, but he takes it off anyway.
Her physically enhanced appearance from the photo that Charles had sent seemed to fit the person, her chest was large and her arms were muscular, but not exaggerated, I passed a suntan lotion on her back, and I felt her body relax as my hands passed over her.
He lies down on the sunbed, and I run my sun-soaked hands down his chest, and he closes his eyes and moans low, and I go down on his belly, and he kind of retreats with the feeling, and I run my fingers down his navel and then down his waist into his shorts.
He's freaked out, but in a good way. He smiles and passes his hand over my face. I get up, grab my clothes, and bikini-walk out of the pool area. I just look back, and he understands that he was supposed to follow me.
Excited, I walk straight ahead and he comes behind... when we are far from thirst, I lean against a tree and hope he reaches me. As soon as he reaches me, he comes before me. I embrace his neck and kiss his mouth, he returns and hugs my waist.
We stood in the hammock for a while, when I took his hand and led him to my cottage... excited, his hand was still a little trembling. I opened the door of the cottage, and asked him to come in. I locked the door, and I see him standing in front of the bed.
I kissed him again and we were in that huddle, when I feel the top of my bikini being untied. I pulled the top off and lowered the thong getting naked. I held his face, and I carried him to my bust and led his mouth over the beak of my breast. He sucks and sucks willingly.
His trembling fingers try to penetrate the middle of my legs, but I hold his hand in fear of him hurting me.
I got down on my knees... under his shorts and then his underpants... his butt was huge and all hairy... and I pulled the glans back to expose the head of the stick... and I stuck my tongue over him... his body was shaking, and I asked him to sit on the bed.
He sits down, I hold his dick in my hands, and I jerk him off for a while, and he moans, and I put his dick in my mouth, and I start swallowing it whole, and I'm sucking all the way down, back and forth.
I was so horny because I was in control of the situation, and he was moaning a lot, and he was holding my hair while he was sucking his dick, and all of a sudden he pulled my head really hard, and I got scared, and when I came to, I watched him ejaculate.
God damn it, I thought to myself, he made fun of me before, that's all I didn't want.
I see the look of disappointment on his face, and even before he could say anything, I hugged him and told him that this was normal and that there was nothing wrong with it.
I put him on the bed, and I sit next to him, and I start pulling random conversations so he doesn't think too much about it, and he actually responded really well, and we started talking about everything.
We lay naked for a while, when I feel his hands reaching up to my breasts to caress them, and then I start running my fingers over his half-erect pussy, and then I hold him and I jerk him off until he's erect again.
I got on top of him and kissed him, and I put his dick in my vagina and I sat on top of him, and I started riding him very slowly so I wouldn't excite him too much, and he was whimpering with pleasure under my body so he could suck on my breasts.
Greg then grabs me by the waist and pulls me off of him, he lays me down and climbs on top of me, I open my legs with the help of his hands, he inserts his dick into the entrance of my vagina and penetrates me, and I groan with a hard-on when his dick goes all the way in.
The weight of his body falls on top of mine, he begins to stock up slowly, but unlike before, I noticed that his body was no longer trembling, it was totally relaxed.
I wrapped my legs around his waist to be snug with him, and he smiled, and he kissed me, and he started hitting me harder and faster, and our moans mixed together, and Greg's roll was deliciously being buried inside me, which made me laugh.
He went deeper and deeper, when he was enjoying intensely, the way he always wanted, his screams of pleasure with orgasm were a clear sign of happiness.
I lie on my back and kiss myself thanking myself, and I repay myself thanking myself for the moments of pleasure.
We lay there for a long time talking, but Greg started to get hard again, his hands and his mouth started to explore my body, his hands went through my breasts, lips and vagina, his mouth kissed every corner of my body.
His gaze was pure desire, a twisted gaze, his half-stiffed dick rubbing against me, while my body boiled with his hands groping every inch of it, and it was then that I remembered the last fantasy I had when I was in that place, whispering in Greg's ear asking for one last favor.
He listens and smiles. I take his hand and lift him from the bed. Naked, we curl up on the bed sheet. I open the door and check to see if there's anyone there.
It was empty. We ran out to a little kiosk that was next to the house. As soon as we got there, we got rid of the towel. I leaned on all fours on the wooden table and spread my legs. Greg came from behind, I grabbed his pussy and I fit it into my vagina.
Greg starts pumping again, covering my screams with his hands, and that feeling of nature's freshness and the urge to be fucking in the fresh air excites me even more.
His pumpkins were delicious and I was already enjoying it, when I look out of the corner of my eye and in the middle of a bush, I see Charles watching us. He even puts the pumpkin out and shows it to me as if to say that later it was his turn.
He knew I wouldn't pass up the opportunity to fuck in the open like last time, so he waited until I showed up, and the craving to be watched while a male dragged me from behind only made me laugh once more.
Greg made fun of us again, and we ran into the cabin so we wouldn't be seen, and at night, we got together to talk at Charles and the boys' cabin, and Greg said that he was kind of suspicious of what his friends were up to.
He said he wasn't mad and that he was grateful for that...
Charles, he joked and said that now it was his turn to go to my cottage, pulling me by the arm... the other boys were also excited about the idea and wanted to go along, but that's another story.