My introduction to anal pleasure This is my first story, I hope you like it.
-- It all started unexpectedly. I was 19 at the time, and had a steady girlfriend for more than a year already - Serena was her name. We were very open with each other sexually, and would often fulfill our fantasies, like doing sex-play in public places or dressing in costumes. We both loved to fuck and to explore ourselves sexually. Serena was hot, having nice sized tits and a big butt, kind of like J-Lo without the all the help money can buy.
I loved to fuck her in the ass, and the night this story begins I was trying to do that, but to no avail. "I'm not in the mood, honey", she told me. "Come on, please. It's been such a long time since I haven't fucked you there, you probably don't even remember how it feels.", was pretty much all I was repeating for about half an hour, already having reached for the K-Y Jelly tube. "I do remember what it feels like, I just don't want to!", she responded. "If you're all worked up, I can give you a blowjob, and I even promise to swallow this time." She knew me too much, and there was no way I could refuse and deal with my hard on by myself.
She took my shorts off, laid me on the bed, and climbed between my legs.
All I did was smile, while she looked at me and, with a small smirk on her face, took my 6 inches cock in her mouth and sucked me for all she was worth. I was in heaven. She would bob her head, lick my dick from tip to bottom, and then keep sucking just the tip for a few seconds, while she stroked my entire length. Her saliva coated my dick completely, and she let me fuck her tits for a few minutes, then went back to blowing me.
My balls weren't forgotten, as she sucked them almost painfully. It was great, but after 40 minutes of this I still had the stamina to keep going for a long time, and Serena had a tired mouth.
"Baby, you know I could come in a minute with some anal sex", I jokingly said to her. "Really? I think you gave me an idea.", she commented, reaching for the K-Y tube. "Turn around and get on all fours." she told me. "Ehr. What?", I did get what she meant, but was unsure whether to do as she said.
"I've thought about trying something some friends have told me. Get on all fours, I will 'milk your prostate' with my fingers, and you'll come right away!", she told me, smiling and expecting the reaction on my face. I definitely looked consternated, to which she replied "Come on, just try it. If you don't like it, we won't do it again." I agreed by turning around and bending over, exposing my puckered asshole to her sight.
She smiled and smacked my ass playfully. As I told her to quit it, she laughed. She began rubbing my asscrack with her hand, almost as if she was combing the few strands of hair there, and after about a minute I could feel her licking my hole's entrance, very softly and teasingly.
I liked it, and she could tell by my hard-on bouncing excitedly beneath me. "I'm think I can come in now", she said, and began spreading the jelly on my asshole, slipping a finger in when it became well lubricated.
The finger entered with ease, and soon she was inserting it all the way and almost pulling off, trying her best to rub down towards my dick, so she could find my prostate gland. Oh, did she find it. I was soon harder then I ever had been, sweating through my forehead and moaning softly. When she asked if she could put a second finger, all I did was moan a low "Yes", and hold on to the exciting feeling of her second finger spreading my anal sphincter.
I believed five minutes hadn't passed yet from the beginning of this experiment, and I was ready to come. In fact, I tried telling her, but just as the words left my mouth, my cock erupted. Hot cum landed on the bed's sheets, and my anus squeezed her fingers.
She just smiled, as her fingers couldn't leave my rectum, and pressed on my prostate again and again. It was the most intense orgasm I had ever had. As the orgasm subsided, she pulled her fingers from inside me with some effort and a little pain for me, and licked my cum off the sheets.
I laid on the bed tired from the orgasm, but incredibly my prick was still almost completely hard from all the arousal. She laid by my side, asking: "So, did you like it?" "Of course!
It was nothing like I thought it would be." "That's good to know", she responded smiling, as she reached for my dick and licked her two fingers, which were a little coated with fecal matter.
Although unclean, this aroused me more, and feeling me getting harder, she asked "you know, I'm all wet right now, and I think I have a dildo that could fit you perfectly. Wanna try it?" "Hell, yeah!" Serena gave me one last stroke and ran to her toys' drawer, as I assumed position. She pulled a small (about 4 inches), not too thick pink dildo with a base like a man's balls and brought it to bed.
I was wide open by now, so she spread a little more K-Y Jelly on my hole and coated the dildo with it, then plunged it deep up my butt. I gasped as I felt myself full again.
She turned me around and laid me on the bed, held on my shoulder with one hand and guided my prick with the other, as she dropped her dripping wet hairless pussy on my dick. Her cunt swallowed me completely, and she rode me like it was her last time, pulling and pushing the dildo from beneath my balls. I tried my best not to come so fast, and my previous orgasm helped me a bit with it, but the dildo was constantly bringing me close to the edge.
I focused on licking her tits and their hard little nipples, as she slapped them on my face while bouncing up and down furiously. Not to long into it, she began to come. Her loud moans, along with the contractions of her cunt, bested me in the battle against coming.
As I filled her up completely with jizz, I felt her coming again and again. When she came back to herself, we both looked tired as hell, but as happy as we could be. She helped take the dildo off and joined me to a good night's sleep.
Much has happened after that, but I hope to tell it in another story.