As you know from my recent posts, I’ve felt like things have been a bit dull the past month, so I am trying to find ways to add some new excitement to our lives. Last week a new strap-on that I ordered finally arrived. I had not told Barry about it, so I decided to surprise him Friday night. It is very similar to my original small strap-on, in that it is very realistic looking and feeling. However, it is larger than what Barry has experienced to date, without being unrealistic.
I decided to create some anticipation for Barry, so I started by sending him a text Friday afternoon when I arrived home from work. I let him know that I had a special surprise for him that evening, but didn’t give him any details. When he arrived home, he started asking about the surprise, but I just told him that he would find out soon enough. As a couple of hints, I left a Fleet enema bottle on the bathroom counter and a tube of lube on his dresser. However, I’m not sure if he saw either of them before dinner. Just before we sat down to eat, I put the strap-on in my harness and put it on under my skirt, which was loose enough to mostly conceal it. However, if he looked closely he would have seen something was there.
When we got up from dinner, I gave him a big hug, making sure I pressed myself against him. The look on his face assured me that he felt its presence and I suggested that he go prepare himself for some fun and to make sure he dressed special for me. That is always our key phrase for him to know I want him to wear more lingerie than just his normal panties. While he was getting a shower and, I assume, using the Fleet, I changed into a tight skirt which clearly showed the girth and length of my new toy and I placed two pillows at the edge of the bed. When Barry entered the room, I stood in the middle of the room and motioned for him to drop to his knees in front of me, and suggested that he might like to get acquainted with his new friend. I then raised my skirt to reveal the new strap-on. Even though I know Barry enjoys being gently pegged, I could see his immediate apprehension. With a little encouragement, it didn’t take long for him to be taking it in his mouth and following my directions of worshipping it. During this time I shared with him that I thought it was time for him to experience a realistically sized cock, instead of the little one we had been using. I eventually had him stand and I took off his cage, so I could better assess his level of excitement. His wee pecker was standing at attention so I knew he was ready. I then took my time with him bending over the bed, making sure that I used plenty of lube and letting him adapt to its girth and length as I eventually let him experience its entirety. I could tell that he was enjoying it by the way he worked his hips in time with my gyrations. I didn’t let him use his hands on himself, but when I finished and he stood up, it was clear that there was a significant amount of pre-cum on the pillows he was bent over. I could also tell that he wanted more stimulation, but I decided that I needed to be satisfied. I then got on the bed and drew his head to meet my needs and he lovingly took care of them. I then told him that it was lock-up time, but not to worry, it would be a long and fun weekend …which it was.
On Saturday, I kept Barry in a gartered teddy, matching panties, and stockings all afternoon and evening. I let him out of his cage most of the time, but kept him busy with household chores which he performed under my close supervision. I made sure that he didn’t have any free time to get himself into trouble. I also had a lot of fun periodically teasing him. I must confess that I truly love keeping him erect and frustrated. By the time we went to bed, I had locked him up again and I could tell that he was really frustrated. But, I again reminded him that the weekend was not over yet and there would be more fun on Sunday.
More about last night later,