Anal trip
Only a week later did they call and invite me
to the office. I was led into the director's office of this company. After talking with the respectable man and confirming the correct filling of my application, I signed several papers.— Excellent. I hope we will all be satisfied with this agreement. Now our employee will pick you up and all you have to do is enjoy yourself.
A rather beautiful girl, dressed like a nurse, entered the office and called for me. Not expecting everything to happen today, I was slightly taken aback by such a rapid turn of events. But gathering my thoughts, I followed her. After walking through several corridors, we entered her office. It slightly resembled a small hospital room.
— I think your name is Sasha, right?
— Yes.
— I already figured that out.
— Great. You indicated that you don't want to know in advance which films you'll be participating in. So now, just obey me and don't ask unnecessary questions. Get undressed.
Taking off my outer clothing, I folded it on a chair.
— Take off your underwear and come to me.
Hesitating a little, I pulled them down and approached her. Katya carefully examined my body, my cock, and my ass.
— Very good indeed, there won't be much work with you. Get on the couch on all fours. Have you ever had anal sex or maybe just played with your ass?
— No sex, but umm… I've played with toys.
— Good boy, nothing to be ashamed of. Now we'll give you a little enema, and then we'll deal with the hair.
— And now, bear with it a little.
A few minutes felt like an eternity; when I was about ready to beg her for mercy, Katya pointed to a door in her office and told me to go there. Running to the door and opening it, I found a toilet and a shower there. After relieving myself, I returned to the couch and Katya repeated the procedure.
On the third time, she went with me, and while I was sitting on the toilet, she prepared the shower and some kind of cream. After I finished, Katya thoroughly rubbed the cream all over me below the head and, after a short pause, sent me to the shower. Along with the cream, absolutely all my hair washed off, and I became smooth as a baby.
Katya dried me off, and we returned to the couch, where I got on all fours again. This time I felt her fingers lubricating my anus, and one even slipped inside me. It seemed to me that it happened by accident, but then it happened again. Each time the finger went deeper, pushing more and more lube into me.
— What a good boy you are. And now, we'll play a little with an inflatable anal plug. So you'll have to endure a bit.
She returned about five minutes later with a small, firm cushion and placed it under my stomach. I could finally lie down, as my hands and knees were already numb. Now I was lying on the couch with my ass raised. Katya pumped the plug a little more and, leaving the bulb alone, began slowly securing my legs and arms with straps to the couch. When I was tightly secured, she left the office.
Lying on the couch with a plug in my ass, I began to understand what I had gotten myself into, and now it didn't seem like a good idea not to know what I was participating in. However, all of this still aroused me greatly, so much so that my cock persistently rammed the cushion. The door opened, and judging by the sound, two people entered the office.
— Sasha, I'd like to introduce my assistant. He will perform an important procedure and then leave us.
She spoke while simultaneously releasing the air from the plug. The plug came out very easily, bringing strong relief and coolness. The male assistant took off his robe, revealing his naked body and an impressively sized cock. Katya sat down near my head, and the man, climbing onto the couch, hovered over me.
— Relax, we're just going to observe your reaction. We simply want to make sure you won't back out at the most crucial moment.
Meanwhile, the hot, firm head touched my anus and began slowly penetrating my ass. Thanks to the plug, the cock entered easily and painlessly. After inserting it fully, he pressed tightly against my buttocks and gave me a little time to get used to it. After a pause, he began fucking me, gradually increasing the amplitude of his movements. I felt very ashamed in front of Katya, but that didn't stop my cock from hardening with renewed vigor. I became so aroused and wanted to orgasm that I started moving my hips and rubbing my cock against the cushion.
— Alright, that's enough. It seems Sasha really liked it. And we don't want him to cum prematurely.
The man pulled out his cock, put on his robe, and left silently. Katya freed me from the straps and asked me to stand up.
— Now everything is ready for the main event of the evening. Let's go.
I gathered my things, but Katya immediately made it clear they weren't needed. We went out into the corridor, walked a few meters, and ended up in the next room. It seemed everything had already started without us. In the center of the room was a lounger; a man lay on it, and a girl, with her back to me, was slowly sliding along his cock. Katya positioned me on all fours.
— You will obey her just as you obey me.
The girl rose up, got off the cock, and slowly turned around. I simply couldn't believe my eyes—it was my sister, Sveta! Naked! What is she doing here!? What should I do!?
— Imagine, a week ago they called me and told me about your application. And they offered me to participate in this, to be your mistress! Then they described in detail what was planned, and I just couldn't refuse. Though I was sure you wouldn't let anyone fuck your ass. But after seeing that hunk fucking you, all doubts vanished completely.
Looking at her more closely, I quickly got distracted from her words; all I could think about and look at now was her beautiful body. Her beautiful breasts and equally beautiful pussy slowly approached me.
— Sveta, this isn't right…
— Shut up! I saw you getting fucked, so now just be quiet, otherwise our parents will find out about this!
Katya came over to us and handed Sveta something. She unfolded it and showed it to me. It turned out to be a miniskirt.
— And now, little brother, let's begin.
Sveta came up behind me and started putting the skirt on me.
— Just look at this disgrace! Your anus is pulsating and shining like my pussy!
— I hope you don't mind if I start treating you like a girl. After all, right now you look the least like a guy… So, you little slut, crawl to your first… second cock of the day.
Sveta swayed her hips as she walked to the lounger, while I crawled on all fours behind her. She sat down next to the guy and took his erect cock in her hand. The cock she had just gotten off of, which was still glistening from her juices. Sveta leaned towards the head, licked it, and then tilted it towards me. I really didn't want to touch it.
— Now take it in your mouth quickly!!!
Gathering myself, I touched it with my tongue, then with my lips, and began slowly taking it into my mouth. Sveta put a hand on my head and began controlling my movements. Now the only thing I could do was take it deeper, without the ability to lift my head. After taking it halfway, I choked and tried to get off it. But then my sister released the cock and put her other hand on my head. Holding me firmly, she began fiercely impaling my mouth onto the cock. Choking on saliva, I took it deeper and deeper until my lips touched his pubic bone and balls. Only then did she let me go, and I finally freed myself.
— Sorry, sis. You just got me so worked up.
Sveta stepped over the man and, aiming the cock at her vagina, sat down on it. She began writhing and bouncing on it, occasionally pulling out the cock to let me lick it, and then continued bouncing.
Unexpectedly, I felt a touch on my ass. Turning around, I saw Katya; she had taken off her robe, revealing her beautiful body clad in lace lingerie, and between her legs was a strapon. Taking it in her hand, she crouched over me and began slowly inserting it. Despite its considerable size, it went in very easily. Pressing tightly against my ass, Katya adjusted the skirt on me and began smoothly fucking me. Now I completely detached from my sister and focused on the strapon. It took a few minutes for my cock to harden again; I really wanted to cum, and unable to hold back, I started jerking my cock with my hand.
— Hands off!
Katya slapped my hand and inserted the strapon all the way into my ass.
— Sveta! It seems your brother wants to cum.
My sister looked at me and reluctantly got off the cock. The man stood up and stepped aside; Katya took his place, and both mistresses sat in front of me. My sister looked curiously at the glistening strapon, took it in her hand, and began playing with it. Watching this and their beautiful bodies, I didn't notice the man had circled around me and inserted his slippery, hot cock into my ass. Grabbing my hips, he began roughly, with slaps, driving his cock all the way to his balls.
Sveta whispered something to Katya and lay on her back in front of her. Katya hovered over my sister and began inserting the strapon into her. It slowly spread her lips and went deeper and deeper until Katya lay on top of Sveta. They merged in a passionate kiss and equally passionate sex. My hanging cock hardened once again. I couldn't bear it any longer; I began writhing and impaling myself on the cock fucking me. A few seconds before my orgasm, I felt the cock pulsing in my ass and a stream of cum splashing inside me.
My vision went dark, and my body shook; my cock began jerking in time with my heartbeat, spurting thick streams of cum, soaking the skirt and the floor. Releasing me, the man pulled out his cock, and exhausted, I fell into a puddle of my own cum.
Recovering from my first anal orgasm, I looked at the couch. Katya was still fucking my sister. Seeing that I had already cum, she touched Sveta's pussy with her hand, and a moment later my sister arched and convulsed in orgasm. When Sveta calmed down a bit, Katya extracted the strapon and left the room. She returned very quickly, holding a rag with which she thoroughly wiped the strapon.
— And you guys are great! I didn't think everything would go so smoothly. When you come to your senses, go take a shower; it's to the left down the corridor, your clothes will be there too. And come by for your payment, don't forget.
She left, leaving the door wide open. Now, after having an orgasm, all of this began to seem disgusting and repulsive to me. Not waiting for my sister, I went to the shower. Under the water, I pulled off the skirt, washed the cum off it, and threw it on the bench nearby. After washing thoroughly, I headed for the exit; along the way, in one of the cubicles, I saw my sister. Slipping past, I got dressed and waited for her at the entrance. When she came out, we went together to the director.
— Oh! My young talents! I hope you enjoyed it and got pleasure from the process.
He began counting out bills; the final amount was so large that the unpleasant aftertaste instantly evaporated, along with the desire to never return here again.
— I really hope you'll come back to us. Come whenever you want; Katya will find something to keep you occupied.
I muttered that I'd think about it, while Sveta happily agreed to come again. We left the office and went outside.
— Sveta, I hope you won't tell our parents about what happened?
— Only if you promise we'll come back here.
— I'm not sure I want that. When I came here, I didn't think I'd be the one getting fucked.
— You yourself indicated that option in the application. And judging by that puddle on the floor, you're being a bit dishonest; you definitely liked it.
Smirking at each other, we headed home.
Several days passed; my sister and I behaved as if nothing had happened. There were no hints or jokes from her. I even started to think that nothing had happened. But one evening, Sveta came into my room.
— Sasha, look what I found in my purse.
In her hands was the miniskirt they had dressed me in back then.
— Why did you steal it?
— Well… as a keepsake. Sometimes I remember how you got fucked in it, and it sends shivers down my spine. Here. You probably have a boner already, huh?
— Alright, if you don't need it, give it back. I'll wear it myself.
All I could do was try to cover my erection a little.
— Where is it? Did you put it on, you little pervert!?
Sveta came over to me and felt it through my pants.
— If you don't want our parents to find out what you're wearing right now, promise we'll go to the studio tomorrow! My condition was exactly that! I hope you remember?!
— O-okay, we'll go.
— Sweet. Good night. And don't make a mess!
Now I wasn't planning to jerk off; I needed to save my strength for tomorrow. I needed to go to sleep, and I decided to lie down in the skirt. The lack of underwear and my erection kept me from falling asleep for a long time, but when I finally drifted off, I sank into the best erotic dreams.
Early in the morning, Sveta woke me up, interrupting my dream at the most interesting part.
— Get up! We need to go! I can't wait any longer!
Hiding the skirt in the closet, I got myself together, got dressed, and we headed to the studio. Arriving at the place, we went straight to Katya's office.
— How glad I am to see you, my sweets! I have a job for you. Get undressed.
Taking off our clothes, we stood next to her.
— On the couch, like last time. We'll give you enemas!
Sveta immediately got on all fours; after a moment's hesitation, I joined her. Katya took two hoses, lubricated the tips, and inserted them into our asses. Like last time, she filled us with water and told us to hold on. Sveta was sent to the toilet first, while I strained with all my might.
— Sasha, hold on a little longer. By the way, how did you like last time? Didn't blame yourself too much for what happened?
— After the orgasm, it felt a bit disgusting, but otherwise, no, I don't regret it.
— Well, that's great. Oh, Sveta is done; run to the toilet.
After Katya performed the procedure on us several times, we stood before her on all fours again. Taking the lube, she dipped her index finger into it and inserted it first into my sister's ass, then into mine, thoroughly lubricating everything inside.__P_