Linda had given me my ultimate birthday present, and I felt compelled to at least try to reciprocate, but to do so would take me far out of my comfort zone. Before describing this adventure, I need to introduce a couple of men that participated. Jim lives next door to our old Condo. We socialized with him and his former partner when we lived there. He happens to be gay and is now "playing the field." His roommate is Allan. Both indicate their relationship is purely platonic. While Allan enjoys sex with either gender, he says that does not include Jim. We know Allan through a work relationship. He is a junior executive where Linda works. In fact, Linda suggested Allan contact Jim when she learned of the roommate possibility. Both of them are in their mid-twenties.
Linda had handed me her fantasy request with the words, "deep and dark." Then walked away. Put simply and crudely, she wants me to be fucked in the ass, while I'm fucking her. I admit I was appalled at the prospect. After all, I was heterosexual and had never had the slightest impulse to be otherwise. I walked after her.
"I'm sorry but I'm really uncomfortable with this."
"Why?" She asked.
"Well, uh, I'm 100% straight and..."
"You think this will make you gay?"
"No, but it could hu-hurt, and I uh, might not be able to stay hard with men there."
"OK, you're frightened and anxious. I would never put you in a situation intentionally that was this troubling for you. Please talk about your fear to me."
"It's just, I don't know, it seems like having sex with a man would put distance between us. I think it would come between us in our relationship."
She thought for a moment. "Nothing I ask you to do could possibly negatively impact our relationship. The reason for that is I would never ask you to do something I believe to be wrong. I have in the past and hopefully will in the future continue to ask you to challenge yourself. But I will not push you away. CFNM lifestyle is about trust between the partners. You and I play with power and control for sexual reasons, but our relationship is built on trust. I love you. Think about my fantasy request in this light and let me know."
I'd started to live with Linda for no other reason but to experience the full range of sexual exploits that she'd opened for me. She had delivered, and now she demanded that I deliver. Rather than have me plan everything, Linda only needed my willing participation. What she wanted me to do was accede to her desire, push my boundaries, and fulfill her fantasy. Despite my reservations, I made the commitment to participate and told her so about an hour later.
She kissed me and said, "You'll love it. I've planned everything with Jim and Allan assisting, so there's nothing for you to do, but show up."
Allan and Jim arrived for dinner on the date planned. She had asked them to honor our CFNM lifestyle and they disrobed in the foyer, folding their clothes on a bench. Linda wore a new dress that was alluring and revealing. We all enjoyed the meal she had prepared and served, together with a fair amount of wine. Higgins and Conchita were away for the evening. When we had finished coffee, she told us that her fantasy was to begin.
We stood naked side by side, while she looked at us. I felt humiliated, being at least ten years older than the other two, but I was fit due to consistent exercise, so I didn't come off too bad in comparison. "Please stroke your cocks. Entertain me," she grinned wickedly.
Jim and Allan got hard quickly but I was having some trouble. "Now I'd like you to form a small circle. Good, now grab the cock of the guy to your right and stroke him." While still feeling somewhat reluctant, it shocked me to realize that, not only did I enjoy the feel of another penis, but I had also become erect. We pumped away for a while and then Linda had us service the guy to our left, thereby allowing us to touch both of the other guy's boners. She left us doing this for a few minutes, actually till I moaned with pleasure.