Girlfriend Finally Cuckolds Pt. 02

After I had watched my girlfriend strip for her ex boyfriend Barry and give him a long, slow handjob, she teased me about it constantly.

"He really loves my ass. Did you see how he couldn't keep his hands off of it?" she'd ask even though she knew very well I had seen and memorized every second. "His cock got soooo hard. I really wanted to be good but I couldn't help taking it in my mouth a little" she'd taunt in something approaching a little girl's voice of wonder.

When I'd ask her if she wanted to do it again...to take it further, however, she had been consistent. "There's too much history. I can't take it further with Barry or I don't know where it will end up." Finally one night while fucking me she offered me a little hope. "Why don't you find a stranger...a gentleman we don't know...to seduce me...to fuck me...wouldn't you like that?"

I came immediately and I laid awake that night starting to think of how I could make this a reality. I lay staring up at the ceiling, my cock hard as I imagined different scenarios of Val with other men. By the next morning I had come up with the obvious plan. Craigslist.

I crafted an ad carefully. I knew that Val would not go for a guy who wanted to just fuck her. She needed to feel comfortable, to be taken slowly. I showed Val the ad asking for a man who would be willing to go slow, to start with dinner or drinks. She had me add an emphasis that the man should have no expectations. I placed the ad and was almost immediately inundated with responses. I narrowed it down to a few and of course when I shared Val's picture they were all even more anxious to make this happen. I decided to give Steve a try. He is older than I am, and wealthier. He suggested we meet in a very upscale lounge in midtown that I knew Val would like.

Val was a little apprehensive about the evening, but agreed no harm could come from meeting for drinks. She seemed to get more excited as we got ready. She asked me to pick out a nice outfit for Steve, and I chose a tight blue dress I always think she looks hot in. I chose black high heels and left her in bare legs. She approved and added an ankle bracelet. She looked irresistible. I felt a little hesitation as I got her ready for her 'date', but I had fantasized about this a lot and was definitely excited to try.

When we arrived Steve was waiting for us at a nice table. I felt a bit under-dressed as we walked into the elegant lounge and I I saw the other customers. Steve who was wearing a simple blue blazer and a white shirt, but it was clear they were of the best material and fit perfectly. He gave me a firm handshake and kissed Val on the cheek. I could tell he was pleased that Val looked just as hot as the pictures I had sent him.

Steve bought us drinks and we talked for a almost two hours. He was assertive but rather endearing, asking a lot of questions about Val. Val, as always was very flirty. She seemed to grow comfortable quickly with this stranger.

Steve suggested we get something to eat and decided he would take us to STK restaurant. We were all feeling a little buzz from the glasses of top-shelf whiskey Steve had ordered. Val seemed charmed by him, even taking his arm on the walk to the steakhouse. When we arrived the hostess knew Steve and we immediately got shown to a table. I followed Steve and Val and watched Steve pull out a chair for Val, then sit beside her. I awkwardly sat across from them, an apparent third wheel as they talked mainly to each other now. As we drank more Val became even more flirty. I felt some jealousy watching my girl giggle as another man leaned in towards her, but I was also turned on to watch her being seduced.

As he had before, Steve brought the conversation to more of a sexual nature, but this time Val was quite willing to go along with it. He made it clear he liked to be in control and Val told him she liked to be in control sometimes but give up control other times. She shyly noted that she liked it when I spanked her. Steve said he had not had a good look at Val's ass except in the picture I had sent and asked her to show him. Val compliantly stood and turned for him and Steve studied her ass, which was wrapped in the tight skirt we had dressed her in. The waiter arrived seemed confused to see her standing, looking away from her companion.

After our meal I left to go to the bathroom, and when I came back I could see Steve had his hand on Val's leg. He moved it for a moment as I returned, but I could tell he moved it back when I was seated. Val looked a little flushed with excitement. Steve told the two of us that we had to come and see his apartment in the West Village very soon. He looked at me this time, his hand apparently now stroking Val's bare leg and asked 'wouldn't you like that?'. My throat constricted a little and I nodded slowly. We toasted our new friendship with a last shot. When we left the restaurant Steve shook my hand and looked me in the eye, the kissed Val on the lips and opened the door for her to get in our taxi. Val squeezed my cock all the way home talking about Steve, how charming he was, and how good the meal was. She fucked me like crazy when we got back taunting me about the new man in our life.