My daughter’s BFF comes to my room. What an incredible surprise!

Continuation of /2026/04/story-50465

Imagine the most beautiful breezy coastal town with turquoise water, a sleepy town feel, and quaint mom and pop shops all nestled in a small town and basically your minds eye is seeing Catalina island off the coast of California. We made it, I had sailed our ship from Newport harbor and arrived at the city of Avalon. We had arrived late last night yet decided to spend the night on the boat because I was spent and our check in at the Hotel Avalon wasn’t until 10AM the next day. That decision led to Kimberly’s actions in which she came over to my cabin and threw herself at me. Kimberly was a 17 year-old goddess, thin strawberry blonde, nice firm tits, beautiful nipples. If you saw her then you would call me crazy to turn her away. Don’t get me wrong, I wanted to fuck her because I had fucked her mother and to me Kimberly was just a younger version of her mother. I couldn’t fuck her because, I think, my daughter was already suspicious of Kimberly‘s intentions. Hell, a blind man could have seen Kimberlys intentions. But, I didn’t want my daughter to lose a good friend over my libido. I didn’t want my daughter to be paranoid throughout the trip and so I had decided that I wouldn’t fuck Kimberly during this trip, I’m, if the opportunity presented itself again.

I would have plenty of time and opportunity when we got back home.

In the morning all the girls were giddy and high energy. I tried not to look but all this young girl ass flying around made my dick grow inside my pants. I felt like such a perv but damn it, I couldn’t stop looking. There were more than a few times in which Kimberly came over to my area and picked up a pin she had lost. Her ass was magnificent: round, firm, tanned and glowing. It was 8am and her ass looked … edible.

We made it to the island. I parked the ship in a berth near downtown. I grabbed our stuff and each girl rolled their own luggage to the hotel. It was a very pleasant walk. Although it was early morning there were already people setting up camp on the beach and the store clerks were busy opening their shops. I checked in. I had procured two rooms for us - two different rooms, one for me and the other for the girls.

We ended up here because somehow, my daughter‘s BFFs convinced my daughter to convince me to bring them on a holiday to this fabulous island. She called it a summer favor and I couldn’t deny my daughter anything.

I told the girls to unpack for our four day trip. I also requested they take a shower and rest up so that in a few hours we could hit the beach and later we would go to get dinner. There is great pizza spot near the beach.

Before leaving i told them that I would take a shower and put on their swim suits so that we could go lay on the white beach with turquoise water facing all the boats with the pictures casino next to us. I told them it was a great backdrop for pics to post.

I heard my daughter say, ughh dad! And then the room burst into laughter. I went to my room and took a shower, a much-needed shower. I felt like I had all the sweat and grime on me. And my dick felt all sticky and crusted from Kimberly’s late night surprise.

The one thing about sailing to Catalina is that it was a lot of work but worth it. Kimberly‘s mom was going to join us tomorrow so I just had to look out for these girls through the next night. I thought about all the firm 16-17 year old asses and scrubbed my dick clean of Kimberly’s saliva. The shower was nice and hot and then the sum of every drop of water felt like a small massage. I was ready to lay on the bed and fall asleep. As I stepped out of the shower I heard a light tapping on my door, I opened the door, and it was one of the girls.

Her name is Bobby. Bobby is beautiful, blonde thin, fair skinned, and she had bubble teen titties and a small firm ass. In my opinion she was anything and everything a young boy would want. The cherry on the cake was that she was quite shy. What an irony to be that shy while having a barn yard smile.

“Hey Bobby. Is everything OK?”
“Yes, sir” said Bobby. are you OK?”

“For sure why do you ask?, I replied.

“Well sir, I saw how much work you put into getting us here and I just wanted to tell you that I appreciate you.”

I hugged her and said, “Well thank you Bobby, but I think you should get back to the girls. I join in a little bit. “

“Sir, may I come in for a little bit?”, she asked.

“Yes but, let me ask you, why would a nice beautiful young teen want to hang out in my room?

Well sir, she said, I heard some stuff about you.

“You heard some stuff about me? What do you mean?”

“Well, said Bobby, Kim said that you have a beautiful penis and I wanted to see it. “

“Oh Bobby. Really? What if my daughter comes to knock on the door?

“Well sir, she’s in the shower or she’s getting ready to go into the shower. So I thought this would be a nice time to come over and talk. I even have Kim ready to distract your daughter if she tries to come over. “

“You’re beautiful Bobby, but I’m not sure I’m ready to do this”, I said. Bobby reached over her shoulder and undid a pin on her sundress. It fell to the floor and all of a sudden she was only wearing beautiful turquoise bikini.
“Will this inspire you sir?
“Bobby, what are you doing? We can’t do this. You’re just a teen!”

“What?, I hear Kim almost fucked you last night!”

“Well that’s different, Bobby, she’s more experienced!”

“I know!, said Bobby, as a matter of fact, how am I supposed to get experience if no one will give me any experience? Am I ugly?”

“No baby you’re beautiful and you’re kind and sweet. You are a real prize. I just don’t wanna get caught by my daughter.”

“You won’t! Kimberly said she’ll entertain your daughter for a bit and if she asks about me then Kim will tell your daughter that I went to the store. So we have some time. May I please see your dick, please?”

Ok beautiful, but, on one condition…
“What’s that?, asked Bobby.

I answered, you have to give me a blow job.

OK, said Bobby.

Have you ever given anyone a blow job?

I have, sir I’ve had a couple of boyfriends.

OK where do you wanna do it?, I asked. Do you wanna go to the bed or that comfort seat over in the corner of the room by the window?

I prefer the bed, said Bobby.

OK, let’s go sit down, I said.

We walked to the bed and Bobby crawled on to the mattress. I was wearing my robe so I just unlashed the belt and it spread open. Truth be told, I don’t have the biggest dick but it’s not the smallest dick either. Bobby was on her knees staring at my dick. I reached over and combed my fingers through her hair.

Do you want to touch it?

Yes sir, she said. I told her to grab it and she did. I told her to kiss it and she did. She even used some tongue. She grabbed my dick and started licking the shaft. She looked up at me and our eyes locked in while my dick disappeared into her mouth. Her eyes never broke contact with mine as she blew me. She took her hands and jiggled my balls and slurped while her mouth took care of my dick. I pushed my dick down her throat and Bobby gagged a little bit and coughed and smiled at me with tears in her eyes.

I wanted to see her ass in the bikini bottom and upon command she turned around and presented her ass to me and boy oh boy what a beautiful sight. I asked her to undo her bra and come lay down to the bed and she did. Teen toys are absolutely fantastic! So firm, so subtle, and so new! I couldn’t believe this girl had orchestrated this. A look at my dick in exchange for a blow job. Lol!

On my God, sir your dick is beautiful. I don’t know if there is any other word I can use to describe it, Bobby said, sir, It’s perfect. Your dickhead is the right size and the curve on it is - wow just wow.

OK Bobby, I said, enough talking - do what I need you to do.

She held onto my shaft and pulled and tugged at my dick. This girl knew what she was doing and so she let go of my shaft, and sat up on the bed. My dick went into her mouth, disappeared all the way to the base her eyes turned a little red, and then she coughed a little as her mouth released my dick and saliva poured from her mouth onto my shaft.

“Oh girl, you know what you’re doing! Fuck! Only a couple of boyfriends?

“Yeah, she said, but they like to have their dick sucked”, she said while giggling. “Wow, you are doing a good job, I said, keep going.

Her head went up and down. Her lips tightened around my shaft, and her tongue swirled around my dick head. Her hands were magnificent, rubbing up and down, inspiring my sperm to reach that line of no return. After a few more strokes, I came in her mouth hard. Her eyes were red. She tried not to let any of it spill. What a trooper!

After I came I flipped her on her back and tore her top off. That turquoise bra had to go. I had her on her back and I tore off her bra and I pinned her arms down and I sucked on her beautiful firm titties. I bit her nipples not hard but enough to get a reaction. I look deep into her eyes and said thank you Bobby that was wonderful. thank you, she said, you do have a beautiful penis, sir.

Bobby, I need to see your pussy, I said as I kissed her.

Her eyes swelled up and she said “well sir - I hope you’re not gonna be mad, but I don’t have a pussy.”

What? What do you mean,you don’t have a pussy? Bobby looked away and started to cry. She said, sir, I have a dick. I’m sorry!

Don’t be sorry, I said, let me see it. She pulled down her bottom and I noticed that they were actually special underwear. It didn’t change the fact that there looked sexy as all hell, but, they were hard and stiff, a containment unit for her little member.

It was so cute. Maybe 1 or 2 inches covered in yellow hair. “oh your dick is so cute”, I said. Do the girls know that you have a penis not a vagina?”

“Some of them do. Kimberly does, sometimes she sucks on it sometimes I fuck her. She also calls it very cute and she likes it up her ass. She says it tickles.”

I took Bobby’s little penis between my thumb and my pointer and I squeeze on it. Does it get hard? not really sir. I take a lot of hormones. It takes a lot for me to get hard. Like, watching porn or watching my friends get naked and fucked… well that’ll do it.

OK Bobby how about we try something have you ever been fucked in your little boy pussy?

Oh my God, sir are you saying what I think you’re saying? Do you wanna fuck me?

Oh yes, darling you are beautiful and my dick is rock solid looking at your little boy pussy, and your hair, and your titties. You are absolutely adorable and I can’t wait to stick my dick inside of you.

Oh sir, thank you so much! I-was so hoping that you would say something like that! I’m so glad that you’re not mad. Oh my God, I was so worried I didn’t want you to have a bad reaction. Oh my God! Thank you, thank you so much sir! I’m so excited. I’m so glad that you’re open-minded.

Mmmmmm, Bobby - shut the fuck up and turn around. This is gonna be good for both of us.

Bobby turned around and I got her on her knees. I literally picked her up, put her on her knees and pushed her back down so that her ass was all up in the air and all I could see was her asshole in the back of her scrotum, I got my old underwear and I wiped her ass and I kissed her little brown star and I smacked her ass cheeks. “Oh my god” she said. I felt so good that I grabbed her hair and I pulled her head back and I said “I am going to fuck the shit out of your ass baby. You’re not gonna be walking right to the beach.”

“Yes daddy. she said. Do you want me to call you daddy? Kim said you like to be called daddy. Is it OK if I call you daddy?

No baby, I need you to keep calling me, sir. Every time you feel pleasure or pain I want you to thank me and say sir.

I can do that, sir, said Bobby with her sweet little ass in the air.

I spanked her, she yelled out, thank you sir. I spanked her … thank you sir. I spanked her harder and harder until I left the handprint on her ass. THANK YOU SIR!

Oh baby, your ass is so beautiful so tiny and your little butt hole is so precious. I put my head between her ass cheeks and I licked, and I squeeze my tongue right into her asshole, and she shivered.

Wait a minute I said, and I got off the bed and I went to the bathroom and yes, sure enough there was complementary lotion so I grabbed it and I took it back to the bed. I said, I’m sorry, Bobby, but I didn’t bring any lube. I didn’t expect to have any sex and so this is gonna have to do.” I opened the little lotion container and spread a large serving generously on my dick and then I spread it on my finger and I pushed it into her asshole. Oh my God!, said Bobby.

Did you like that Bobby?, I asked.

Bobby whimpered, “yes, sir, that felt good.”

“Well if you think that felt good I hope you like it when I break your ass” I said. I put the tip of my head into her asshole and I started thrusting in slowly

“oh my fucking God!, she said.

Do you like it, baby? Yes, I mean, sir yes sir … oh my God I feels so good. You’re so big. Oh my God I feel like you’re fucking my bladder.”

Oh baby, just you wait, I said.

I grabbed her hair and I pulled it back and my dick went far deep inside of her. All I could hear was her breathing deep. She made this weird noise. She was in pain and I saw the teardrops falling on her face, but it gave me brevity to push even harder. Her reaction made me feel so alive.

“Oh sir, thank you. oh my God I think I’m gonna fucking come!

I lifted her up with her body impaled up on my dick. I walked to the mirror and I told her to jack herself off and she did and right when I started coming she started coming on the mirror. There was come all over my mirror.

Fuck, she said, fuck that was wonderful. She popped off my dick and I grabbed her hair and pulled her head and face near my dick and told her to lick all that shit off my dick she looked at me, eyes staring at me and she opened her mouth, stuck out her tongue and engulfed my dick.

She reached for my dick and I smacked her hand away “no baby clean that shit thoroughly” I said. When there was nothing left on my dick I told her to jack me off she did and my sperm went all over her tits, her beautiful small round firm tits.

Was that what you wanted Bobby? is that what you came here for?

“Oh, yes sir i feel so good I didn’t think you were gonna fuck me, but oh my God it’s everything that I dreamed about.

Sir this can’t be the only time! I need to have you from now on let me! She said.

Let me ask you, Bobby have you fucked any of the girls?

No, just Kimberly. Jasmine has seen my dick. Sometimes, she touches it but she’s kind of clean. Clean, like your daughter. Your daughter has never seen my dick. I know that Kim ate her out once at a party - we were playing truth or dare.

Oh my God Bobby you’re such a fucking snitch. I love it!, I said while laughing. “You better go in that fucking shower and clean yourself off and go back with the girls. Tell them they all have to get ready so that we can head down to the beach.
“Yes, sir”, she said as she walked into my shower.