BOB: “Yeah but that lube was super slick and it caused me to cum.”
LILY: “Okay, Next time you apply it. I just had hopes of you doing me this afternoon.”
BOB: “Yeah I’ll do it next time. Or maybe I’ll make you take it without lube.”
LILY: “I don’t think so. That’s liable to hurt.”
BOB: “It’ll only hurt if your ass is tight.
My dick will split it open.”
Internally I was laughing as I knew there would not be another opportunity for him to get in my ass or any other orifice for that matter. I retrieved a wet washcloth and tossing it to him said “you better get cleaned up and get a maid up here later this afternoon. Next time, you better plan on staying up longer.”
BOB: “You’re just lucky I slipped up.
Otherwise, I was gonna pound that tight ass of yours every which way I could.”
After he dressed and left, I enjoyed my dinner and the remainder of the wine, smiling that I had popped his cork so easily. I was glad Olivia had mentioned how the lube was prone to cause some guys to cum so easily. As I ate, I took time to assess my situation.
My mind was all over the place with the events. I was into my fourth day as a woman and had knocked off 4 of the 5 conditions.
I had quite enjoyed my time with Vickie and sex with Steve almost went unnoticed because I was still active with Vickie. My session with Olivia was amazing and one I would be thrilled to continue. I figured with the cream and lube she gave me, I could tolerate the last task. She certainly had opened my ass to the pleasures of anal. I was grossed out by Bob’s session but had extracted some revenge and was plotting the rest.
And what was gonna happen when I finished? Would I suddenly change back to a guy? What was Tatyana going to do to me if I succeed? What if I fail? Enough worries. It was Saturday and tonight would be my best shot at finishing as the clubs would be packed. I just had to swallow my male ego and take some unsuspecting guy to bed.
I headed out at dusk. I dressed in what I hoped was mildly provocative but not slutty.
I knew of a couple locations that had dancing and considered them the best opportunity for assessing the field of candidates. I knew what I didn’t want as a partner; some macho jerk that might take control and alter the plans for his own gratification; some whimp that might pop like Bob before entry or some guy that might be playing multiple girls and leave with someone else. What I didn’t know was who I did want. I had never tried sizing a guy up for sex so I was a little lost.
The first location was packed so I passed figuring I could always return. The second was a much better fit as it was busy but not full. There was a general mix of couples and singles. I ordered a drink and staked out a small table from which I could see most the activities. I briefly pondered the option of hooking up with a couple.
I would be oblivious to the guy if I was busy with his partner but then how do you ask a chick ‘Hey can I get your guy to fuck my ass while I do you?’ I decided to let things take their course. As the first hour drug on, I had opportunity to dance with a few guys and was even bold enough to ask one sitting with a girl. Actually, I asked her if she would mind if I danced with her man. She was cool with it but obviously not going to let it go far.
As the second hour broke and I was nursing my third drink, a pair of guys walked in. As they found a table, I perceived the taller one was the other’s wingman. I watched the shorter guy swing and miss on a couple attempts at meeting ladies. He definitely had the better looks and was far more outgoing but was too much like the clichés. The tall one just seemed to be there and not really add much to the activities. I decided he might be a good target.
I strolled over and asked if he would like to dance. The short one was as surprised as the tall one but we headed to the dance floor. As we moved, I learned his name was Jerry and the other guy was Tim. They were roommates and worked offshore for two week shifts. They would be leaving again Sunday evening and wanted to hit the clubs one last time. Over the course of the next 90 minutes, I danced with Tim, Jerry and a couple others. Figuring Jerry as my best option, I kept him the busiest.
After the two bought a couple more rounds, I thought I would roll the dice and see what will happen. It was still early enough that if Jerry bailed, I could consider alternatives but late enough that we could get to his place. I picked a song that warranted me dancing close in front of him and drug him onto the floor without asking. As the music played, I would move my butt closer to him. Since he didn’t back away, my next move was to brush the front of his jeans with my ass.
Again, there was no retraction by him. Knowing the song was more than half over, I grabbed his hands and pulled him in close. As he pressed against me, I gyrated my ass against his crotch. He obviously enjoyed that as he started pressing back, almost with thrusts. I smiled to myself as I felt he was more than willing. After the song, we returned to the table.
Tim used the next song to troll for a hook-up while we caught our breath.
Leaning toward Jerry so that he could hear me, he did the same.
I asked, “You like my ass? You didn’t seem to mind us dancing.”
JERRY: “Absolutely, you have a nice tight butt.”
LILY: “Well that nice tight butt has an itch that I think you could scratch.”
Jerry with a slightly confused look on his face said “What?”
Repeating myself: “How would you like to scratch that ass?” and I ran my hand up his thigh.
Jerry with a big grin crossing his face: “Would I ever.”
LILY: “You understand I’m talking anal.
Have you ever done a girl’s ass?”
JERRY: “Yes and no. I’ve heard about it from guys and seen it on porn but you’d be my first.”
LILY: “If you want to try, let’s get out of here and I’ll lay down the rules for you.”
Jerry pulling back a little: “Rules?”
LILY: “You’ll understand, just makes it more enjoyable for both.
Let me visit the Ladies Room real quick and you can let Tim know you and I are heading to your place and not to disturb us if he brings a girl home.”
I slip into a stall in the Ladies Room and dab a little of Olivia’s desensitizing cream on my hole. My finger felt good moving around the hole and I took an opportunity to press it in some. I wondered if I was actually starting to enjoy anal sex regardless of my history.
I met Jerry at the door and he said he was ready.
As we step outside, I ask: “What did Tim say?”
JERRY: “He said go for it, He only hoped that he would find someone too. Do you mind a short trolley ride? I told Tim he could take the car.”
LILY: “No problem.”
As we rode the trolley to the apartment, I explained, “The rules are simple. Since this is your first time and I don’t want either of us injured, you do things at my pace.
Unless I indicate otherwise, I am gonna ride you, kinda cowgirl style. I apply the lube to your cock so that I know it’s covered. If you get excited and start thrusting hard into me, I’ll sit down on you until you settle back down. I just don’t want you rearranging anything inside.”