I’d seen Kate a couple of times and we got on well. After the third date, we started sleeping over - a nice meal, a few glasses of wine, a shag and then off in the morning. After a week or so, whilst we were engaging in pillow talk, she confessed that she’d love to try anal sex but was worried that it’d hurt. I was no help, on the few occasions I’ve tried it, it has been painful. Kate had read that a massage often helped to relax, so I offered.
“Would you mind?” she asked.
“Of course not.”
“And I have a butt plug I picked up from an Ann Summers party, we could perhaps use that to open me up, see how it goes.”
I couldn’t wait. Our next date was the Wednesday and after I arrived at hers, we had a meal and sat chatting and then I offered to start the massage. She was more than up for it, so we went up to her bedroom, put a towel down and I told her to strip off and lay down. I got the oil and butt plug from the bathroom and made a start.
Not wanting to freak her out, I started at her neck and shoulders, then worked my way down her back on to her legs. I used long, hard strokes and took my times, enjoying the light mewling noises she was making. I made wide loops across her buttocks, moving down her legs to her toes, then back up.
“Work on my arse,” she muttered dreamily and so I did, pressing deep and hard, really working into the muscles.
That process kept her cheeks opening and closing, showing off her arsehole and the lower portion of her pussy lips. I kept working the cheeks, pushing deeper between them with each stroke until I couldn’t help but hold them open to stare at her hole. I bent forward and kissed it gently and then began lightly biting her buttocks. Her murmurs of appreciation spurred me on, so I licked my index finger and bent forward again.
Kate positioned herself so that she was more comfortable, pushing her arse up as she did so and as I licked and kissed her buttocks, I tapped her arsehole gently with my finger. The first time, she groaned out loud but the more I did it, the more the groans became purrs. I kept pressing, harder and harder until my finger slid inside her. I pushed it in to the knuckle, still kissing and licking her and she said, “Oh fucking hell, Pete, fucking hell.”
I picked up the butt plug. It was black, fairly short in length but quite thick at the largest part before retreating to a narrow neck. I rubbed a liberal amount of oil on it and then rubbed my oily hands all over her saliva covered asshole. Spreading her cheeks with my fingers, I began to rub and touch the tip of the plug to her hole. I felt just a little tensing from her and rubbed gently for a little longer, letting her return to full comfort.
“Relax and enjoy it,” I said and started to push the tip of the plug inside her.
I waited for her to get comfortable, then worked the tip in and out going deeper with each stroke. Her hole looked very sweet as it continued to relent and allow the plug to go further. I heard a small groan as the widest part was reached. Giving her time, letting her cheeks close around the plug and my hand, I rubbed her cheeks with my free hand.
“Yes,” she gasped, “go on, push it.”
I started stroking her again with my hand, pulling her cheeks as wide as I could and put pressure on the plug. It sank further and wow, what a sight. The wide portion breached her and the plug sank fully into her and she moaned.
”Okay, flip over onto your back.”
I helped her move and most of the movements made her shiver. “That feels so good in my arse,” she said, “I never knew it’d feel like that.”
I laid her down, smeared more oil on my hands and began to massage her. I spent a lot of time on her tits, rubbing them and the nipples until they stood proud. I worked further down her body, avoiding her pussy, working on her thighs and legs and feet. Every now and again, her toes would curl.
I moved up her legs and decided now it was time to start working on her pussy. I worked her outer lips, gently moving them back and forth and up and down until she was biting her lips and moaning. Then I parted them, touching the inner lips and her clit. There was a lot of juice there, it was literally trickling down her arse.
As I rubbed her, slowly wanking her off, the sounds she was making were just amazing to listen to. I reached down and moved the plug slightly, trying to keep up a rhythm.
My cock was rock hard now, but I tried to forget about it, wanting to finish Kate off and see what happened next. I started to play more seriously with her clit, licking it and sucking it and the harder I pressed, the more rapid her breathing got. Within minutes, I felt her tense and her legs began to twitch.
With her clit between my lips, my tongue flicking at the tip and my hands wrapped under her touching the plug, she tensed completely and came with a wonderful full body shaking. I stopped licking her, knowing how sensitive she got and resumed some light massage on her belly until her breathing returned to normal.
She opened her eyes and smiled lazily at me. “How about if I roll over again?”
I kissed her deeply, pulled off my shirt and slid my trousers and boxers down. She grabbed my cock, wanking it lightly. “That’d be great,” I said.
I helped her roll onto her front and she pushed her arse up while I slid a pillow under her belly. I checked her arse. More oil had dribbled around the plug and I began to move it around, then slowly and carefully began to remove it from her arsehole.
Her arse began to close so I slid a finger gently inside. It felt wonderful. My cock was raging by then, so I slid a condom on, slicked some of the oil over it and positioned myself on the bed.
“I’ll be gentle,” I said.
“Fuck me, Pete….”
I propped myself up, hands on either side of her and slid my cock up and down between her cheeks. I leaned back, knelt up and looked down. The head of my cock touched her arsehole, making it pulse slightly. I leaned forward, taking my weight on my arms and pressed my cock against her sphincter. I leaned further, nibbling her shoulder and put my mouth beside her ear.
“This looks great, my cock is sliding into your arse.”
“Does it look good?”
“Fucking brilliant.”
I pushed and she gasped as her arse relented and I slid in until my balls were against her wet pussy. It was so tight, it was fucking incredibly and I felt so horny I wasn’t quite sure how long I’d last. I began to move, slowly thrusting into her and moved so that I could play with her clit at the same time.
I wish I could say that I lasted for hours but it wouldn’t be true. I flicked her clit like I was an Olympian and as soon as she’d cum again, her arse pinching my cock, I came too. I kept pumping inside her, not wanting this to end and then dipped my head forward, to kiss between her shoulder blades.
“Was that what you expected?” I asked, once I’d got my breath back. “Because it was better than I thought it was going to be, much better.”
“Oh yes,” she said, “we’re going to do that again!”
