29/03/2021
Of course, I had to have several drinks to help quell my apprehensions about going through this plan to strip in front of Thad and even then I wasn’t sure I could go through with it.
When I mentioned about strip poker, Thad’s shyness surfaced. He looked at both of us and asked if I really meant that we would be playing for our clothes. Gary again said yes and asked Thad if he was up for it. For being such a tall, muscular and good looking man, Thad is EXTREMELY shy and bashful, especially around the opposite sex. He had never dated or had a girlfriend and it was all due to his extreme shyness. We could tell that he wasn’t sure about stripping in front of me and Gary did his best to assure him. He told Thad that we were doing this to help him with his shyness and to give him some basic experience with women. Finally, with his meek nature he said okay and I dealt the first hand with nervous shaky hands. I was shaking as much as Thad, partly because of my shyness but also due to may apprehension combined with a growing sense of sexual arousal.
Gary lost the first hand and took off his shirt. I lost the second hand and the realization that I had to take something off hit me and I wasn’t sure if I could do it. I looked at Gary with the look of wanting him to bail me out yet all I got from his was a lustful smile. I took a big gulp of my drink. I took a deep breath and unbuttoned and removed my shirt. Thad’s eyes were doing their best not to stare, but he couldn’t help himself. From what I knew, it was the first time he had seen a live woman in a bra and knowing this was an especially sexy bra made me wondering if I was revealing too much.
The hands were pretty even and at one point we were all sitting there in just our undies – the men in tshirts and underpants and me in bra and panty. I lost the next hand. Oh no, what should I take off first? By this time, I was becoming more sexually aroused but was still very apprehensive. I turned my back to Thad and asked him to unhook my bra. I took a deep breath as I felt his shaky fingers fumbling and told him to just slide the hooks to the side and I felt my bra release. As my bra released, my heart raced faster and faster. Holding my bra to my chest, I turned to face Thad and invited him to take the bra off me. He very meekly reached out and took my bra and I moved my hands and let it fall in his hands. Poor Thad was more embarrassed than I was and it showed, as he openly stared at my breasts.
Thad lost next and took off his tshirt. Gary lost his tshirt next. We were all down to our last item. As fortune would have it, Gary lost the next hand. He stood up and allowed me to take his undies off. Thad lost and Gary told him to stand and let me take his off. Poor Thad looked like he was about to be executed as stood up and faced me. I revealed his sizeable erect manhood that was dripping from the tip and Thad looked like he wanted to run out of the room. I told him he should be proud of his equipment and not embarrassed to show it off. He about jumped out of his skin when I licked the tip of his manhood to catch his dripping excitement.
I was last to lose and I sat there and turned to Gary, He told me to stand and let Thad take off my panties. Thad began to protest and Gary told him it was okay and that he needed to do this sometime and better now with us than with a girl he was trying to impress. His fingers were still shaking as he fumbled around trying to figure out how to take my panties off. Gary told him to put a finger inside each side of the waistband and pull them down all the way and let me step out of them. He did as he was told and I took another gulp of drink and a deep breath as Thad pulled my panties down. When he leaned back up, his nose brushed my pubic hair and it sent wild sensations through my body. He apologized and I told him no apology needed.
There I was, naked with my husband and Thad, whose eyes were glued to my body. Gary asked him if he had ever felt a woman’s breasts and Thad said no. Gary told Thad to feel my breasts and I took another deep breath and gulp of my drink as his hands enveloped by breasts. It felt great, exciting and I found myself getting sexually aroused.
Gary then asked Thad if he has ever seen a woman’s pussy up close and Thad said no. Gary hoisted me up onto the table and slid me over right in front of Thad and then he pulled my legs apart. My feet were resting on Thad’s thighs. His eyes were locked on my womanhood and Gary told him to go ahead and touch and put a finger inside me. Poor Thad’s hand was shaking as his finger made contact. I grabbed his hand and shoved his finger into me. He was shaking so much it almost felt like a vibrator. When his finger went in, I instantly had an orgasm. I could feel Thad’s finger moving around inside me and Gary told him to put his finger in his mouth and taste my sex. He did and let us know that he liked it. Gary told him to bend down and taste me directly with his tongue and he did, causing me to again have an orgasm.
We had set rules that touching was as far we would go, at least for now. Gary asked Thad how he was feeling and all he could do was smile. Gary asked me how I was doing and I smiled back at him. Gary then told Thad that if would like to learn more and get used to being naked with a woman, that we would have him back again. Thad said he would like that. He looked me up and down and told me I was very beautiful and thanked me for doing this and that he looked forward to the next time.
As soon as Thad drove away, I jumped up on Gary with my arms around his neck and my legs around his waist and told me to take me now. While making love, he asked me how I really felt about the night and I told him I was so close to calling it off as I didn’t think I could go through with it, but now am glad I did. He asked me how far I was willing to go the next time and I told him that was up to him and Thad, but if given the chance, I would seriously entertain giving him his first lesson on intercourse. I didn’t have to ask Gary how he felt about it cause as soon as I said that, his manhood got extremely hard and huge.
We talked a lot about the next time with Thad, over the next week but I wasn’t sure I could go an farther than I had.
Guess that will be our next posting.