Mining Gem's New Passage

After we got back from the conference Gem and I met up regularly and she fucked me every which way. Things were going great until one day she mentioned that she'd met someone else; I was married and knew it had to come to an end at some point but it was disappointing when it came nonetheless. Our sessions slowly became farther apart until eventually, one night, Gem told me she was serious with the guy and we'd have to stop. Then a few weeks later she came in to work with a big old rock on her ring finger. It had been nearly a year since we got stuck in Zurich and whenever I thought back to that night my cock stirred, but it seemed it was all over.

I was working away on some dull report when I felt a presence next to me, I looked up and it was Gem.

"You going to the conference this year?"

"Thought I might. You?"

"Yeah, I enjoyed it last year!"

My cock started to rise; I wished she wouldn't tease, especially as she wouldn't be following through this time.

"Somewhere warm this year, we won't get trapped."

"Shame," and she winked at me and then spun on her heels and was gone.

Later that month I was sat on a plane with Gemma beside me flying off to the Mediterranean coast. It was the week before Gemma's wedding and we chatted about life in general. Then she looked me in the eye and said "There's something you can do for me whilst we're here."

"Oh yes?" my heart raced.

"Yeah, there's something I want to try but not with Brad, I want to know if I like it before I let him try."

I was intrigued but before we could continue the pilot came on and we went through the landing preparations.

We checked in to the hotel and as it was warm, around 35C, I pulled my shorts on and headed to the pool. Gem was already there, in a blue one-piece swimsuit. She had such a wonderful body I never knew why she didn't show it off more. We chatted and ordered a couple of beers. After about an hour Gem went in to the pool, she did a few lengths and them came to the steps to get out. As she climbed the steps she revealed that sexy body, it reminded me of the Halle Berry moment. First her long dark hair, swept back and dripping water down her back, then her tight tits, squashed flat by the swimsuit but still clearly visible and well formed; the water must have been cold as her nipples stuck out hard and clear, ready to be sucked. Next her tight stomach, toned but not muscled, followed by the mound of her sweet pussy outlined by the tight, wet, clinging swimsuit. I thought back to 12 months previously, the first time I had seen that pussy shaved bare and smooth; she'd said it was because of the swimming so I imagined it would still be the same; how I wanted to pound that tight pussy again. Finally her legs, again athletic but not too muscled, I remembered those thighs straddled across my face, the musky smell of her wet pussy as she lowered herself on to my face, and I missed our sessions. My cock remembered too and was ready to escape from my shorts.

Gem returned to her sun lounger and lay face down on the towel, her butt cheeks making a smooth curve outlined by the tight material of her swimsuit. I wanted to bury my face in to that butt again, to lick the smooth skin and delve into that tight hole. I wondered what she had meant on the plane. No time to worry now, she was getting married in less than 5 days and I had no chance. To prevent any more pain I excused myself and agreed to meet Gem for dinner.

We met up in the bar; Gem already had a large glass of red wine. She was flushed and I could see she was getting tipsy. She had on a short dark blue cocktail dress and was sat across from me on a bar stool, her smooth legs crossed but leading the eye up to the point where the dress just shadowed the place I wanted to see. She uncrossed her legs and I got a brief glimpse of her pure white panties, now we were in Basic Instinct, I had to look away but as I looked up I realised Gem was watching me, did she flash me deliberately? No that was wishful thinking!

We ate dinner and took another bottle of wine. The flush on Gem's face was starting to spread on to her neck. We chatted and just after I'd signed the check she leaned in towards me. "You know what I mentioned on the plane? The help? Come to my room in 15 minutes and I'll explain."

Gem left and headed for the lift. I left it the required 15 minutes and then followed up to her room. I knocked lightly and a few seconds later Gem opened the door; she had the hotel robe on. She stepped back and beckoned me in. I walked over to the bed and sat down on the edge, my heart racing, was I going to get one last go in that pussy before she got married? She'd said something about trying something new but we'd pretty much gone through the book.

Gem came over and straddled across my thighs, looking me deeply in the eyes she said "There's one thing I've never tried. I want to try with you because if I don't like it I don't want to let Brad and then let him think we can do it again." She paused then continued looking deeply straight in to my eyes "I want you to take me in the ass."

My cock sprang forward, and my heart skipped. I hadn't expected this but I'd been everywhere else, had let my tongue explore that tight hole and this would be the final icing on the cake. "Are you sure?"

"Yes, I thought long and hard, if I do it with you and like it I can let Brad, but if I don't like it I can just not start with Brad. What do you think?"

She stood up and let the robe drop to the floor, I was faced with that taut body and couldn't resist. "Always happy to help!" I stood up.

Gem pushed me back on to the bed and I sprawled backwards. "I'm in control," she said.

She reached down and roughly pulled my shoes and socks off, then my trousers and pants; I was left in only my shirt. I could see now why she'd been drinking so much, Dutch Courage. I scrambled backwards and lay across the bed. Gem went in to the bathroom so I had enough time to discard my shirt. When Gem came back I saw she had a small bottle of lube, she squirted some into the palm of her hand and then grabbed my cock and smeared it on. It was cold but the combination of having Gem once again naked in front of me, the anticipation of what was going to happen and her rubbing my cock meant it didn't matter.

Once I was lubed up Gem straddled me again and roughly grabbed my cock, she positioned herself over my cock and then lined me up with her tight hole. She pressed down but her ass muscle closed tight and with the lube my cock swiftly slid off and up towards her pussy. "No, not in there, I know that feels good, in the other one!"

Gem once again positioned me and this time I felt my head nestle in to the beginning of her tight opening. Once again she pushed down hard but her ass was so clenched I slid off again. "Shit, why won't it go in!?!"

I grabbed Gem and rolled her over "You're trying too hard, you need to relax, here let me..." I got Gem to lie on the bed face down, her head resting on her arms. I'd spotted a bottle of plain massage oil so grabbed that and poured some in to my hands. I rubbed my hands together to warm the oil and them smeared it across Gem's shoulders; she let out a gentle sigh. I positioned myself so I was straddling her thighs sitting just below her butt, my cock resting on her cheeks. I massaged the oil in to her shoulders and felt them go from knotted to more relaxed almost immediately. I applied more oil to my hands and started to massage her back, I felt Gem relax and sink into the bed. I applied the oil all over her back and worked my way down to her butt cleavage. I took some more oil and went for broke.

I applied the oil to Gem's buttocks and started to massage it in, she was completely relaxed now, I rubbed her buttocks a while each time spreading her cheeks a little. I moved my hands up and slid them down between her cheeks, she tensed slightly but then relaxed. With my right middle finger I slowly slid down her crack and across her tight opening, just like I'd seen her do with her own finger to collect my cum on many occasions. I slipped my oily finger slowly in to her ass, she moaned and wriggled but didn't tense. I rotated my finger a couple of times to get her used to it and then started to slide it slowly in and out. Gem let out another soft moan "Good" she sighed.

I removed my finger and massaged her cheeks a little again then returned to her puckered hole and this time inserted 2 fingers. "Oooooh, ahhhhhh" she tensed. I held my fingers still once again for her to get used to the sensation and quickly she relaxed again. I slid my fingers in deeper and then withdrew; her ass closed tight again as they came out. There was no more probing to be done, now was the time.

I adjusted my position forwards so that the tip of my cock lined up with Gem's ass. I applied some more lube then taking a good grip of my shaft, I positioned my cock at the opening to her ass and slowly applied pressure, I felt her ass tense "Relax, it'll be OK" then slowly I felt her muscles relax and watched as my cock head slowly slid forwards opening her asshole wide and slipped in. Her ass snapped around my cock just behind the head, Gem let out a deep groan.

I stopped and waited for a reaction, good or bad. Gem just lay there with my cock head buried in her tight asshole. Then she said "That's good, how far in are you?"

"Just the head."

"Go deeper."

I needed no second invitation. I pushed and slowly my cock slid further in, assisted by the amount of lube I'd applied. I got to the fat part of my cock and stopped again to let Gem get used to it. "Is that all in now?" she asked.

"Not quite."

I felt Gem push back with her pelvis and the last part of my cock slipped in, her sphincter snapping tight around the base of my cock; it was like wearing a cock ring. It felt so good, smooth, warm and extremely tight, I knew I was the first there. I relaxed and lay on Gem's back, nuzzling her neck. "Fuck me now, fuck me in the ass." she said.

I started to pump, slowly at first pulling out a little and slowly sliding back in; I didn't want to hurt her. She started to moan with each stroke, a pleasurable moan. Soon the feeling of that tight ass around my cock started to get to me and I became selfish, increasing both the speed of my thrusts and also the power behind them, soon I was thrusting hard and fast into Gem's sweet ass. Her moaning got louder and she hid her head in the pillow. I thrust hard and fast and after a few minutes I shot my load deep in to Gem's ass. Her ass gripped me tight and my cock pulsed with each spurt. I felt my shaft being coated with my own cum.

Once the pulsing of my cum in to Gem's ass had subsided I pulled my cock out of her ass, otherwise with the cock ring feeling I wasn't going to go down, and rolled over on to the bed. Gem lay there face buried in the pillow for a few minutes then lifted her head and looked at me. "Thanks, I needed that."

"So, how was it?"

"OK, but nothing like being fucked in the pussy, and I couldn't feel you cum in the same way."

"And Brad?"

"No, I don't think so, I think you can keep my ass cherry forever!"

After that the conference was dull, Gem wouldn't let me back in her room, she was saving herself for her wedding, and that was the end of that.