“I’d be happy to do it, but only when you are ready. Like I said, if you don’t want it, it won’t be a good experience.” I assured her.
Sarah also texted me, “Sorry about ganging up on Abby, I think without realizing it, I got really excited by the thought of you in my ass. Is Courtney with you?”
I confirmed she was.
“Is she needing you or can I try out that cock in my ass?” Sarah asked.
“Oh, fuck that’s hot,” Courtney laughed, “You are usually good for three rounds in a day, so go for it. Fuck her ass.”
“Courtney says you can come over and find out what the hubbub is about.” I told her.
“Be right there.” Sarah replied, and my phone went silent.
Sarah arrived shortly later, wearing a long coat, and four inch heels that looked like they belonged on a stripper. Once the door closed, she removed the coat revealing a sexy transparent light blue silk chemise, the matching thong easily visible through the transparent fabric.
“I hope you liked it. I know you are going to be introducing me to anal sex, but I wanted to feel sexy before you blow my mind penetrating my ass.” Sarah informed me, and the girl was certainly on form for being sexy.
The chemise did nothing to give Sarah modesty, it merely enhanced my desire to touch that which it covered. Her aroused nipples and areolas were easily visible. Her breasts were held in a flattering position, pressing her breasts into a nice cleavage, despite their small size. Her heels made her stance enhance her booty and I was pleased with the resulting figure.
The resulting erection was clearly visible bulging in my pants. Sarah licked her lips unconsciously, as she eyed the results of her sexiness. She rolled her hips as she walked to me, which if she wasn’t wearing lingerie, intent on getting my cock in at LEAST her ass, she would have looked like one of the hookers in the early grand theft auto games… but since she checked all the above boxes, holy fuck, it was sexy.
“Wow, Sarah!” Courtney muttered appreciatively. “If you aren’t careful, Tom will cum in his pants.”
“Then we should get him in the bedroom and out of those pants.” She said, trying a sultry tone with her voice. She looped a finger in the collar of my shirt, and gently led me to the promised bedroom.
Courtney followed, appreciating the effort Sarag was putting into seducing me. I put up no resistance.
When Sarah had led me to the bed, she gently guided me to a seated position and she spread her legs, straddling me and lightly sitting on my lap. She began kissing my neck slowly untucking my shirt and letting her fingernails dance across my skin as she removed it.
She pressed on my chest, guiding me to lay back. She ran her tongue down to my neck, and never have I regretted having chest hair so much as when Sarah skipped directly from my collar to my nipple.
She slipped off my lap, abandoning my newly aroused nipple to undo my belt and pants. She gently tugged and I lifted my legs, allowing her to remove my pants. She reached up my boxer leg and began playing with my balls in my boxers as she returned to my neglected nipple.
I decided that hot as this was, being passive was not all that I wanted, and I began to feel her breasts through her chemise. I figured a little reciprocity was in order. The top of the chemise was easy to slip aside freeing her breasts to be groped directly.
Sarah extracted her hand from my boxers and tugged my boxers off. She sunk down, unfortunately removing her supple breasts out of my reach, but as compensation for moving her breasts out my range, her mouth enveloped my cock. She could still only manage about four inches in her mouth, but it felt great. She made eye contact as she swirled her tongue on the dome of my penis, and I almost exploded there.
“Now, if I keep this up, you’ll drop your load in the wrong orifice.” Sarah lamented. She climbed up on the bed. “Now, do you want to unwrap me? I hear you have to prepare my ass, or this won’t go particularly well.”
I rolled over on top of her, pinning her to the bed as I kissed her and began squeezing and rolling her breasts in my hand. I saw, out of the corner of my eye, Courtney grabbing the half full tube of lube and setting it on the bed, just in reach. Then she grabbed her phone and began recording me as I sensually mauled my harem girl.
I decided that as hot as it would be to fuck her in her chemise, just pulling her thong to access her holes, the lube had a tendency to stain and I didn’t want that. I wanted Sarah to be able to do this again.
So I worked her chemise over her head, and with Sarah’s cooperation she was soon laying in front of me wearing just a silky, transparent thong. I kissed her neck, and teased her nipples for a moment. Then pulled her thong off in one slow pull. I started playing with her pussy, letting my index and middle fingers slide up and down her slit, before inserting them to hit her g-spot and going back to stroking her outside.
I was buying time. Time for the near climax Sarah had almost given me to fade. I wanted to fuck her ass, and I wanted it to last. If I had just gone for it as quickly as possible, I wouldn’t have lasted ten seconds inside her ass before climaxing. I wanted my climax to paint her bowels white with my sperm, but I wanted both of us to get more than five seconds of the sensations involved in me fucking her ass first.
Finally, I felt my climax had faded enough I should be able to give Sarah a decent ass fucking, I opened the lube as I pulled my fingers from Courtney’s pussy, and I applied a generous drop of lube to my fingers, I then began playing with Sarah’s asshole.
Sarah seemed to judge if she liked her backdoor being played with, “It is definitely a new sensation.” She murmured.
“Relax, if your muscles are tense it will be more uncomfortable getting used to anal play.” I told her.
Sarah took a deep breath and I could feel her anus loosen. I continued to play with her pucker and massage her ass cheek.
“Oh, that is much better.” Sarah breathed.
I kept massaging her ass until I decided to press inside, her lubricated and relaxed ass allowed my finger entry with simple pressure.
“Oh. Lord…. that feels…” Sarah breathed.
“It is a bit of an adjustment at first, but if you let yourself get used to it, it feels really good.” Courtney assured her.
“It only was uncomfortable for a second.” Sarah assured us, “I’m already used to it.”
“Okay, I am going to go deeper and start opening you up.” I explained.
“Do it.” Sarah affirmed.
I worked my finger deeper and began doing small circles to stretch out her muscles. Sarah moaned as her ass accepted my full finger and began to feel my ministrations. Sarah’s ass was incredibly tight, but once I got past the sphincter, the inside was soft and gently squeezed my finger.
I sucked her nipple to try and keep her aroused and was rewarded with more moaning. Sarah hitched her legs up higher, her knees almost to her shoulders, to make sure I had good access to her asshole.
As I felt her asshole loosen up, I gently set my middle finger against the pucker wrapped around my index finger and began applying pressure to her to let her know my next finger was coming. Sarah moaned and bucked her ass against my fingers, asking for me to insert it. I complied, slipping my second finger into her slowly stretching ass.
“God, it is a stretch, isn’t it?” Sarah gasped. “Mmmm, but once it is in… I like that. Oh, I really like that. Probably not every time, but it definitely feels good.”
“His fingers are good, but his dick is better.” Courtney assured me. “And there is no fingernail on his penis, his fingernail can sometimes nick you in the ass and that is not fun. But his dick, oh it is great in your ass.”
“Give me a minute to finish preparing your ass, and I’ll show you how it feels.” I told Sarah, “It won’t be much longer now.”
“Oh, I’m excited for it.” Sarah purred.
I started to apply lube to my penis with my left hand as my right kept working Sarah’s ass and stretching it. Sarah was doing a great job relaxing her ass, and that let it stretch quickly. Being able to spread my fingers in her ass was really helping too, it let me gently spread the sphincter and anus and preparing her insides to be fucked. I was getting really excited to fuck Sarah’s ass.
“Okay, I think you are ready. Try to stay relaxed, if you tense up, it can undo all the work I did to prep you.” I told Sarah.
Sarah nodded.
“Grab your butt cheeks and spread them so I can get a good angle on your anus.” I told her.
Sarah reached down, her arms going under her legs, and she spread herself for my eyes and impending cock. Courtney got in position to record her friend’s virgin ass to accept my cock.
I put my head on her slightly open pucker and applied gentle pressure. Her ass provided almost no resistance as my cock stretched her ass and sphincter.
“Fuck!” Sarah moaned.
I waited, my cock just inside her ass. “Let me know when you are ready for me to give you more.”
“Just a second…” Sarah gasped, waiting for a minute before continuing. “Okay, it almost hurt, that stretch, but I’m good now.”
I pulled back, just a tiny bit and began to rock, allowing myself to gently slide deeper into her with each thrust. Despite the amount of prep work I had done, her ass only accepted me a half inch at a time, at most. Resulting in me slowly drilling into Sarah’s ass.
Sarah’s ass felt amazing. I was starting to get an idea of the differences in women’s anal cavities, as I was fucking more and more of my harem in the ass. Suki was easily the tightest, and I hit the curve into her bowels most easily. Courtney had the best muscle stimulation in her ass. Brittany was the best at working her ass on my cock. Sarah, her as was the softest and most inviting. Her ass was begging my dick to fuck it. It didn’t clean to and milk my dick like Courtney’s did, or as tightly as Suki’s did, but once it was fully opened for my dick, Sarah’s ass just let me fuck it without protestation.
“God, I see what you were saying, Courtney. His dick feels so good in my ass.” Sarah confirmed. “Oh, it’s so good.”
I kept thrusting into her. “Let me know if you are wanting it faster or harder.”
Sarah gasped, “Hmmm, show me what you can do. Pound me.”
“If you’re sure…?” I verified, and Sarah nodded.