When we left our lascivious pair they were waiting for Theodora to return from her roof top hot tubbing. What I might have failed to mention was that we were waiting on the bed, naked. When Theodora returned to the room and came around the corner to use the shower to wash the chlorine off she seemed a bit taken aback to see us nude. At this point I still had no idea what was going to happen. Would Theodora decide that a threesome wasn't for her when it came time for her to take that step?
After her shower V enticed her into bed for a massage but I still wasn't sure what was going to happen. Theodora had told me that she wanted us to do things to her and not to expect too much in reciprocity, so her passivity wasn't unexpected. After the massage I decided that I would have to take the bull by the proverbial horns and move things forward. V and I took up positions on either side of her and began to play with her nipples. Theodora has magnificent nipples and it wasn't very long before I was sucking on one. V followed my lead and began to suck on Theodora's nipple too. After a few minutes of sucking I asked Theodora if she'd like to give flogging a try. Though Theodora had been spanked and paddled she had never been flogged and was a bit worried about it. We explained that flogging sounds much worse than it was. She laughed a bit and then said "OK". That was to be the pattern for the rest of our playtime. I'd suggest something Theodora would laugh and then say to go ahead.
V demonstrated each of our three floggers on Theodora's ass. Theodora's preference was for the stingy pigskin flogger over the heavier and more thuddy calfskin flogger. We were careful not to flog her too much after the bruised ass paddling incident of a few days earlier. After the flogging I told Theodora to roll over onto her back because I was going to get the rope out and tie her up. She laughed a bit and then said "OK". Unfortunately the hotel bed did not offer any convenient securing points, the bed frame went all the way to the floor so I ended up securing one arm to the bathroom doorknob, the other arm to the beside table and tied her ankles to the table at the end of the bed. I hoped that Theodora wouldn't test the strength of the attachment points because this was more restraint in principle than restraint in practice and we left the ties loose. Theodora commented that she wasn't tied very tightly. After she was secured V and I took turns flogging her tits and pussy.
Feeling like the Director of the events of the day I told Theodora it was time for her to get fucked in the ass. As I untied Theodora, V put on her harness and I passed big purple to her. As Theodora moved down to the end of bed and positioned herself on her hands and knees V whispered to me that she was concerned that big purple would be to big for Theodora to take anally. I assured V that it would be ok but didn't tell her that my confidence was because I had tried the dildo in Theodora's ass the previous night. I watched from the side as V slowly inserted the head of her cock into Theodora's ass. This was not going to be a DP night for Theodora but I was happy helping her fulfill her fantasy of being fucked in the ass by a woman while I watched. V motioned me over to her and pointed down to her feet, she was standing on her toes so I moved behind her to steady her. This involved me leaning against her back and reaching around to hold V's breasts. Looking over V's shoulder I had a great vantage point as she enthusiastically fucked Theodora in the ass. Theodora had one of her hands between her legs as she played with her clit. Theodora was making more and more noise and surprised both V and I when she shot off V's cock when she came. Theodora curled up on the bed with a pillow while V went into the bathroom to clean up. She practically strutted out of the bathroom with her hands on her hips and a big grin on her face.
We decided to take a break for dinner at a nearby Thai restaurant so we all dressed and headed out. V was more talkative than normal, it was only later that Theodora and I found that V had partaken of a few shots of liquid courage over the course of the evening. When we returned to the hotel V attempted to entice Theodora to join her while V gave me a blowjob. Theodora demurred, saying that she had her fill of sex for the day but she did get out her camera and photograph the event. Theodora would occasionally show me the camera when she had a photo she was particularly proud of. V and I then transitioned to fucking while Theodora transitioned to shooting video. I felt like a porn star fucking V with her legs spread and sticking way up into the air as Theodora videoed the action. At some point Theodora left us to finish our fucking and went into the other room.
After we were done V and cuddled for a few minutes before she dressed and headed off for home. Though not conventional I considered our first threesome to be a roaring success. Theodora and I slept soundly that night and did some more sightseeing the next morning before I drove her to the airport for her flight home.
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