My first anal experience.
Several weeks had passed since I had first met Brooke at the salon. She had me over several times and each time she would take me to the balcony overlooking the beach or in her living room and I would be on my knees with her seated with her cock in my mouth. Our encounters were not purely one sided with mutual oral happening a few times. Never knowing what we would be doing but always open and doing as she instructed.
One afternoon when I arrived home from classes there was a message on the answering machine. Pressing play I heard the assertive voice of Brooke and my pulse quickened and I began to get aroused knowing I'd be seeing her. The message said for me to come by at 10pm. I went about the rest of my day excited but with no idea of what was in store.
As always I promptly arrived at her door at 10pm. She opened the door and my heart skipped a beat as I saw her. She was in a short silk robe tied at the waist showing her amazing figure and ample bosoms. Looking down I could see her large flaccid cock hanging freely under the robe. She took my hand and pulled me in for the deep kiss typical of my arrival.
As I stepped in the door closed behind me she told me to take off all my clothes. As I began to take off my shirt a lady walked in from the balcony wearing a small bikini. I paused and said I'm sorry. Brooke turned to me and said, “this is Sabrina, a friend of mine.”
“Don't stop,” she ordered. The two lovely ladies watched me remove my clothes and stand before them nude.
Brooke took my hand and led me to the balcony. She sat in her chair and her robe opened revealing the cock I knew would soon be in my mouth. She looked at me and said, “you know what to do.” I looked back at Sabrina and she was coming to the balcony also. Brooke smacked my ass and I spun around. She looked at me and said, “I didn't say look at her.” I got down and began to suck her cock as Sabrina watched.
As I stroked Brooke's massive cock with my hand and my tongue working the head to pleasure her I heard Sabrina say something and Brooke responded. Not paying much attention to the conversation but on doing as Brooke taught me to bring her to orgasm. It wasn't long before she grabbed my head and forced it down as her cock pumped several big loads of cum down my throat. She moaned softly as I worked the last bit from her.
Brooke leaned forward and we kissed. I turned and saw Sabrina had been watching the whole time. I blushed and looked away when I saw she was stroking her own cock. I was oblivious to the fact she too was a trans woman.
I looked again at the size of Sabrina’s cock and she was not as big as Brooke but had a large mushroom head and curved slightly upward shaft unlike Brooke's straight shaft. Brooke leaned into my ear and said, “go suck her cock.” I looked at Sabrina's face and she had a slight smile and a nodded gesture to her cock.
I walked over and knelt before Sabrina's slender body, her jet black shoulder length hair shined with the light of the moon. I reached for her cock and she said, “no, hands.” I slowly moved forward, my mouth slightly open. The head of her cock opened as I took her large mushroom head in my mouth and my lips closed around it on the shaft. I continued to take her cock slowly going down till it was all in my mouth and throat.
My mouth was tired and my throat sore from Brooke's massive cock and Sabrina's head and curved shaft made me gag more as I took all of her cock. My lips around the base of her cock she put her hands on my head and slightly thrusted upwards to go deeper. Gagging as she held me down for what seemed an eternity she let my head up and I let the cock fall from my mouth. Spit and saliva dripped from her large head and back to my mouth. She smiled and said, “you're going to want to get that cock very wet.” I looked over and Brooke smiled and said, “do what she says.”
I continued to work Sabrina's hard cock with my mouth. Slowly going all the way down and back up. Stopping at the head rubbing my tongue on it to get a small squirt of very thick pre-cum. I went back down and again gagged on the large head on her very hard cock. This time as I took in the air as her cock fell from my mouth she looked at me and said, “stand up and turn around.”
I stood and turned my ass facing her as I looked out at the ocean and clear sky. Sabrina grabbed my checks and squeezed them with a satisfied mmmm. I feared what might happen next. She stood behind me with her cock pressed against my ass as she reached around and rubbed my chest while kissing my back. Her breast against my back still in the bikini top. She moved her hands to my upper back and said,”lean on over.” I put my hand on the rail and leaned slightly forward. She rubbed my back and said, “more.” Now on my elbows she said forcefully, “lower.” My chest now on the rail, my hands resting on it in a pushup form.
I began to tense up with an expectation of what was about to happen. I knew it might happen but expected Brooke to be the one to take my anal virginity. Sabrina rubbed my back and then down my ass to my thighs. Her hands on my inner thighs she pushed outward and I moved my legs till she stopped pushing. Now spread wide laying on the railing she put her hand on my lower back. I could tell from it she was stroking herself with the other. I looked back and she was looking at my ass before her rock hard cock in hand.
I began to rise and she held me down with her hand. I looked over at Brooke as she sat watching. Seeing my face she said, “like before you can say no if you don't want to do this but you have enjoyed sucking cock. This is something new to try.” I knew she wouldn't say anything if I did say no but I was frozen there again, surprised and confused about what was about to happen.
I stayed in position.
I had thought about how I had women bent over like this and now the role is reversed. Did I want to be fucked.
Sabrina laid her hard cock on the crack of my ass. She ran her hands over my back and my ass cheeks. She said, “Relax, it will be easier.”
Much easier said than done was my thought but I responded, “Yes ma'am.”
She pulled my cheeks apart. She pulled back and I felt her hard cock moving down my ass towards my virgin hole.
I tensed as I felt the head against my hole. I could feel how hard it was. I could stop this now I thought. Then I felt something wet and warm hit my hole. I looked back and she was spitting down a few times. Then rubbing the head on my spit covered hole. Looking at her I could tell she wanted my ass badly. Looking in my eyes she said, “I love the feeling of first penetration.” As she pushed slightly against my hole and it tightened more she repeated for me to relax and pushed harder.
My head was spinning as I watched over my shoulder as the scene behind me. What am I doing? Is this really happening? This is happening. I'm going to be fucked.
My whole body tensed as she pushed harder and my hole began to open. She applied more force. My heart was racing. My hole resisted her rock hard cock. It hurt as her cock stretched me open. I let out a painful grunt as I bit my lip to fight back the scream I wanted to release as her head slid in.
She stopped and was not moving.
She was looking down at her hard cock in my ass. Looking up at me she said, “I love how you are fighting it. So very tight.”
Then with a grin she slowly pushed more and more of her cock in me. Her cock was hard. I could feel the large mushroom head going deeper in me. She let my cheeks go and put her hands on my hips, in the same way I had done with women.
She was balls deep into me and stopped. She was savoring the pleasure and thrill of my virgin hole. She slowly pulled back till the head was about to pop out. I could feel it just inside me. Then slowly back in.
My very tight hole gripped her hard cock tightly. Her cock felt enormous as she began to take slow deep thrust.
It hurt like hell. Looking back at the pleasured look on her as she took me I knew that it would be a long fucking.
It wasn’t long before I started to relax and open up to her. Sabrina said, “There we go.”
The thrusting started to build in speed and force. I began to sweat and grunt with the pain of each thrust. Sabrina started giving my ass a brutal pounding. Each thrust eliciting a painful grunt or moan out of me as I gripped the railing. My painful sounds from her hard cock being driven into me seemed to fuel her.
She began deep hard thrust driving her cock with punishing force. It hurt because each thrust was brutal. I looked over and saw Brooke was stroking her cock to the scene before her. She was enjoying Sabrina’s primal breaking in of my ass.
Sabrina slowed and I felt her slowly pull out. I relaxed, thinking it was over then I felt her large head push back in my hole. I grimaced from the pain of it going back in and she pulled it out again. She repeated several more times. Each time it hurt but I realized that I liked it. I enjoyed being on the receiving end. She pushed inside me again and the pounding returned and each thrust hurt but I wanted it. I looked back at her hot sweaty body and she saw that I was enjoying it. I watched her work to deliver each punishing thrust.
Looking in her eyes I said, ”fuck me.”
She said, “What?”
“Fuck me!”
It was like those words energized her as her grip on my hips tightened and began driving her cock brutally into me.
It felt as if the abuse of my hole by her would never end. I could feel that mushroom head moving inside me with each thrust.
Sabrina’s breathing got heavier and the pounding was faster with shorter thrust. I felt her cock swell. My mind raced as I realized she was going to cum.
She ripped her cock out quickly and I cried out from the pain.
“Fuck,” she said breathlessly as I felt her cock explode a load of her thick hot cum on my ass and back. Her cock rested in my crack. I felt it jump with each squirt of cum. It was hot, thick and a lot. I collapsed on the railing taking in deep breaths. My ass was hurting from the primal pounding from Sabrina.
Sabrina collapsed in her chair feeling satisfied in taking me as Brooke walked over and kissed me and said, “let's get you cleaned up.”
Brooke led me to her walk-in shower. My legs were weak and my ass sore. I could feel Sabrina’s thick load on my ass and back.
I finished showering and went and laid on the couch. Lying there with my ass hurting and my body exhausted from the night's events. Brooke sat next to me on the couch as Sabrina went to shower.
“Did you enjoy that,” Brooke asked as she rubbed my back.
“It hurt more than I expected. Yes ma’am I did. ” I responded looking up at her.
I wasn't lying either. I wanted to do it again but I wanted her. Brooke leaned in and we kissed. She covered me with a blanket and went to her room. I dozed off thinking of all that had just happened that night.
Re: My first anal experience.
