Discreet Encounters - Class is Out

'I tell you what,' I quickly added, 'maybe we could try a little finger play and see how that goes. And then I'm sure there might be an opportunity for more when the weekend's over.' I winked at her.

'Good idea', Barbara clearly approved, sensing that Lucy didn't want to be left out entirely from the weekend's more intimate activities. 'Why don't you kneel down on all fours with your chest on the ottoman?'

Lucy followed her instructions.

'Lots and lots of lube', Barbara said to the entire room. 'It's not like your vagina - your anus has no natural lubrication at all and its surfaces are a lot more delicate. So, lots of lube in there first and lots of lube on him - or on any toy you use. And make sure it's warm it before you apply it unless you want to tense up and ruin things!'

She passed me the bottle of lube that she'd been holding tightly in her hand and then she used her hands to part Lucy's butt cheeks, exposing her little rosebud to the gaze of the room.

Lucy giggled. 'I really didn't think I was going to be showing that off to you all when I came here this weekend.'

I put a little of the lube on one of my fingers and touched it lightly on the tightly-closed opening, just to get her used to it. In my experience, emptying half a bottle of lube onto a girl's behind in one go isn't a very friendly approach. She gave a gentle murmur as I touched her. I added a bit more lube to the finger and touched her slightly more firmly, exploring all round the hole. After a few moments, I poured some more lube directly onto her. I'd kept the bottle clamped between my thighs to make sure it was warm. I also added more to my finger.

I teased my finger round the opening, working the lube in, and then teased the very tip inside her. She let out a cross between a moan and a groan as she felt the intrusion. She didn't seem to be objecting.

'I'm going to enter you now', I warned her, 'but if it hurts, tell me and I'll stop immediately.'

Lucy nodded.

I slipped the finger in halfway up to the first knuckle until I felt some resistance.

'I want you to push back, squeeze, almost as if you're trying to push something out.'

I felt her respond and her sphincter expanded. I took the opportunity to slide the finger in deeper and began working it around. She gave out a few pleasurable moans as the tip of my finger excited the nerves inside her. As she got used to the feeling I probed deeper, causing her to gasp a little.

'Still ok?' I wanted to know.

She nodded again. 'It's different, it's not at all what I expected.'

I continued exploring inside her for a few moments. She seemed to be focussed intently on the new-found sensations.

'You're going to need to be much more open if you're going to take a cock in there', Barbara said.

I took the hint and slipped my finger out of her. Before she had a chance to close up, I lubed up a second finger and began to insert the two of them. I could feel her stretching as they entered her.

Lucy squealed. 'No, stop', she insisted. 'That's starting to hurt. Can you just go back to one finger? - that was lovely. Maybe we can do more some other time?'

I did as she asked and the pleasure quickly returned, but it was soon clear that she was unlikely to cum through this stimulation. Maybe one day she'd reach that peak but, sadly, this wasn't the time for it. Now, if I happened to have a free night in the not too distant future...

I continued for a few more minutes and then slipped my finger out of her and made clear it was over by disappearing off to wash my hands. Barbara passed Lucy some tissues to clear up the lube that was leaking from her.

Lunch was taken round the table in the kitchen. Everyone was still naked and it was very obvious that all the girls had acquired a new-found confidence in their bodies. All sat firmly upright, breasts, large and small, jutting proudly forwards, heads held high, all laughing and joking. It had been a very successful weekend and I hoped Barbara was pleased with the way it turned out. Sadly, though, the final meal was soon over and we all made our ways up to our rooms to dress and pack.

Gathering in the lounge for our final goodbyes, each of the girls came up to me and kissed my fully on the mouth, one or two hands slipping between my legs for a final caress. Then, in ones and twos, they departed, leaving just Barbara and me.

'I think that went very well indeed', she said. 'Better than my wildest expectations. Maybe time to get a date in the diary for next year's class?'