Monday, June 13, 2011

He said: She's Here

When you know two women and one of them tells you that she has thought about using a strap-on on another woman and the other one tells you she has been watching strap-on porn what would you do? That question may not be as easy to answer as you might expect especially when the first woman is V, your current lover and the other woman, who has decided she wants to be called Theodora for this story, is someone you have known for years, visited with a few times over perhaps five years, is a sometimes lover and a very special friend. Now the question of what to do was academic when Theodora was living on another continent but becomes much more important when she told me she would be an hour away from V and I for a few days.

Now V and I have a good thing, how would she react to me suggesting a threesome? V likes to have 'planned out' and Theodora is much more a 'fly by the seat of your pants' woman. In the end I took the proverbial deep breath and broached the subject to both of them and they both agreed that it was worthy of further discussion. I arranged for both of them to connect to each other via IM and left them to get to know each other. Over the weeks that passed, V expressed some frustration about not being able to pin Theodora down over what would happen. Would we even have sex with each other? All I could do was sympathize with her and tell her not to worry too much about it. We'd get together, have dinner and drinks and see what developed.

Now you have enough back story to understand what was in my mind as Theodora and I drove in my car to her work assignment in the city about an hour from ours. The closest international airport is in my city and I had offered to drive Theodora there and have dinner with her. It had been a few years since I had visited her and though we keep in contact via IM and the occasional Skype call it was good to see her in person. We chatted on the trip down as I described some of the sights we passed on the way. We arrived, I got her checked into the hotel and we went to a nearby restaurant for dinner. After that we picked up some wine and beer and headed back to Theodora's room to have some drinks and visit a bit. I couldn't stay too long, but so she didn't feel lonely after I left I brought her a bag of items she could use to occupy herself on those lonely hotel nights. Some of the items were practical, like our big purple jelly dildo but I also brought along a few items to whet her sexual appetite including our ropes. Before you go 'ewww' about us sharing our toys be aware that we clean them thoroughly and use them with condoms. The plan was for her to finish her work commitments, then she would return to our city for a few days of sightseeing and perhaps some bedroom fun. Theodora had also brought along a few toys of her own which she showed me and which she and I tried out with quite satisfactory results. I should probably tell you that Theodora was the first woman I ever spanked and one time I spanked her so hard with my hand that my hand was sore for days. Somehow a ping pong paddle had made its way into Theodora's kinky care package and the combination of wine and a bag of sex toys resulted in her being soundly paddled with the ping pong paddle.

A few days later I picked Theodora up to return to our city. A previous commitment meant that V would have to meet us partway and take Theodora to her hotel. Theodora and I met V at a restaurant in a suburban mall. I had one of those heart stopping moments when as we walked into the restaurant a young woman said "I know you!". Luckily she had been a server at a restaurant near my office and remembered me from the few times I had visited there. After a few quick introductions and some chit chat I handed Theodora and her luggage over to V with fingers crossed that things would work out in the three or four hours they would be spending together without me.

When I arrived back at the hotel and we were preparing for a trip the rooftop jacuzzi by changing into our bathing suits Theodora scolded me for the enthusiastic paddling I had given her. Evidently when she had decided to give the purple dildo a try she had been surprised by the sight of her bruised backside in the mirror where she had hoped to observe her pleasuring herself. I did not feel guilty in the least because she had encouraged me and I was the one who had decided she had been paddled sufficiently. If I would have followed her instructions she would have really had a bruised backside instead of the the three or four small ones that she did have. After this this brief discussion off to the roof we went. Though it was rainy and cool the water was nice and hot. Theodora particularly liked luxuriating in the water as the rain fell. The rain started out fairly lightly but increased in intensity as we floated. V wasn't going to stay with us that night and Theodora and I reluctantly bid her adieu until the next morning. Theodora and I spent some more time sitting in the hot tub then we returned to her room for some visiting.

We met V for breakfast the next morning after which we headed off to Northbound Leather to show Theodora a glimpse of the kinky side of the city. Then it was off in my car for some sightseeing in the pelting rain. We returned to the hotel and went for a swim in the pool which was very relaxing but also got me horny. I discreetly groped at V which did not help my horniness level. When the discussion about perhaps returning to the rooftop hot tub came up I demurred, though the hot tub was nice it was raining even more than the night before and the thought of rain water running into my eyes just didn't seem that alluring. While Theodora went to the roof V and I returned to the room where we relaxed on the bed waiting for Theodora to return.


  1. Well aren't you a lucky guy!!

    I totally want to hear about any strap-on fun, if it was had or if it's had in the future, such a fantasy of mine.

    Can't wait for the next installment!

  2. Well we'll have to see what we can do about fulfilling that fantasy. Which is your preference, giving or receiving?

  3. Well I've always quite liked the idea of receiving but just lately I've been turned on thinking about would quite like to try both. Would love to be able to cross that off my bucket list sometime soon.