I still had no idea about the specifics of the plan that Trish was hatching trying to get her gay friend and my long-time best friend to agree to what was essentially getting fucked by a man. By me! But I can assure you that the next couple weeks was filled with some seriously good oral sex.
After the first two times Trish gave me the blow jobs that she promised to seal her deal, I sensed that she wasn't as inexperienced as she made herself out to be. She could tease and arouse and stimulate as well as anyone. True, she may have had some bad luck with the few men previously in her life. And perhaps the fact that she trusted me helped her be open and experiment, but she certainly didn't lack for skill or enthusiasm. And I was pretty sure Stacy didn't know of this ongoing deal, so I couldn't talk about this with her.
One evening, Trish called and asked if one of us could come pick her up from a town about 10 miles away because she felt afraid of the buses there. Stacy was a bit under the weather and asked if I would go.
So I drove out to the suburbs and found Trish, and we started driving home. After a couple minutes of small talk, Trish said, "Do you want to hear the details of my plan Jason?"
"I'm still worried Trish." Perhaps my participation was unfairly solicited.
"Don't be Jason. It'll be just fine." As she said this, she unbuckled her seat belt and slid next to me on the bench seat of my truck. She caressed my ear and reached her hand down to the front of my shorts, and then started stroking my bare thighs. "How about another lesson Jason? What else can you teach me about the art of fellatio?"
"I think you're doing pretty well Trish. You know you don't have to do this."
"I know. But I really want to. I like to." She then felt my cock, starting to harden at her touch and with her whispering sexily into my ear. "Ooohhh...not hard yet Jason? Well, let's take care of that. I've wanted to feel you grow hard in my mouth. That would be a good thing for this lesson." She quickly undid the belt and opened my shorts and I pulled my hips up to let her slide my pants down just a little. Without further preamble, she took my cock fully in her mouth and held my deeply as my cock quickly swelled in her hot, wet mouth.
"Oh Trish...that's crazy...feels so good."
"Uh huh," was all she mumbled, not removing my cock from her mouth. I could feel her tongue around and around and within a couple minutes, I was hard and pulsing in her mouth.
"I am driving, don't forget Trish...wouldn't want to have an accident now."
"That's ok Jason...just keep your eyes on the road and I'll keep my mouth here," she said, stopping only to say this and resumed sucking and stroking my hard on.
I stroked her hair and felt her lips surrounding my cock. Luckily the traffic was light and it was now dark outside. "Trish, that's incredible. It isn't going to take me long like this."
"Ummmm..." was all she could say, clearly not stopping until her task was done.
As we got nearer to the apartment, I was looking for a secluded place to park for a few minutes, so I wouldn't crash the car and I could finish without some passerby looking in the window. No sooner than I found a church parking lot to stop, than Trish doubled her efforts and had me coming in her mouth, filling her with gobs of hot, sticky cum.
"Oh god Trish...that was pretty amazing."
"You can come so quickly...you're so easy. Nothing to coming in, what? 10 minutes?" Trish smiled, looking up at me with a drop of white fluid at the corner of her mouth, which I wiped from her lips, lest she show up at the apartment with a come stain on her face. She sucked my finger saying, "got it all now didn't I?"
"Yes you did...crazy..."
"Now, let's go home." I drove a couple more minutes and parked a short walk to the apartment. I did notice Trish took a quick sip of wine when we got there, smiling at me, not wanting to kiss Trish with the taste of cum in her mouth.
Two days later, another early morning knock on my door brought an almost naked Trish into my bedroom.
"Can I come in?"
"Sure...what's up?"
"Well, I'll bet you are," she said, reaching for my crotch and finding an already hard cock. "Does it ever go down?"
"Not when I'm thinking about you and your sexy body and your very good oral skills."
"Well, I have a request for my next lesson."
"What's that?"
"I want you to show me where the prostate is. I read that a prostate orgasm is very intense for a man. And I know that when Stacy and I do some anal stuff, it's pretty wild."
Her hand was kneading my cock through the sheets and then she quickly stood up to remove her robe and slide in the covers with me.
"So you guys do some anal play, huh?"
"Yeah...we've discovered some erogenous zones with that."
Her hand resumed stroking my hard cock and then she kneaded my balls and her fingers were definitely headed towards my ass too. She rested her head on my stomach and I felt her breath on my cock as she stroked me and played with my balls and the skin on my inner thighs. I caressed her back and her hair, and then felt her mouth lower to encircle the head of my cock. I could only groan as she softly did her tongue twirl trick, which made me even harder.
She did this for about 10 minutes, just softly sucking on the head, licking and stroking the shaft of my very hard cock. Then she sat up to kneel between my legs, never taking her hand off my slippery cock. She looked up at me and said, "I brought something."
"What would that be?"
"This." She took a small bottle of some lube from the pocket of her discarded robe at the foot of the bed.
"Prepared, aren't we?"
"Indeed...we use this quite a bit..."
She squeezed some onto her index finger and then slowly slid her finger towards my ass.
"I haven't done this very much Trish...be careful."
"I will honey....don't worry." She pulled my legs open and pushed her slippery finger inside my ass and I let out a small yell as I felt her finger penetrate me. "Shhhh..."
"Sorry. Just not used to that."
"Tell me where it feels best." Her finger slid further and further into me and I felt the back of her hand against my skin, knowing that she was fully inside me. Now she didn't have big fingers, buy my ass wasn't all that accustomed to anything in there.
"Up towards the front..." I told her, as I felt her finger wiggle and find the sensitive tip of my prostate. "There Trish...that's it...I can feel that...soo good..."
"I can feel that there too Jason. It's a bit different...but I can feel it. Does that make it feel good?"
"Oh yeah...that's good. That's very good." She resumed wiggling her finger giving me a prostate massage.
"And if I did this, it would be better, right?" She said, as she lowered her mouth to my cock and took me deeply into her mouth. The combination of her finger in my ass and her mouth on my cock was incredible and in a matter of moments, I let out another small yell trying like crazy to be quiet, as my orgasm erupted from me and spurted into her warm and awaiting mouth.
"That was incredible Trish...so intense, so different."
"You came a lot Jason...a lot. And I could feel you tighten around my finger when you came. Way sexy."
"You're the way sexy one. I hope I didn't yell too much. I couldn't help it."
"Thanks for lesson three..." she said, slipping on her robe and exiting quietly.
After a week had gone by, I was beginning to wonder if Trish really had this plan for Stacy to get fucked by me. Part of me was hoping it wasn't going to happen and another part of me was anxiously waiting for the plan to hatch. During that time however, Trish didn't disappoint or sway from her promise.
One quick blow job in the living room while Stacy was showering and another morning visit, each time coming into her waiting mouth was enough to make me think this wasn't going to last forever.
We were cooking together one night, and when Stacy went to the bathroom, Trish said to me, "tonight's the night."
"What do you mean?"
"Dummy...tonight is when I think I can get Stacy into it. She wasn't feeling well last week, and then she was having her period. So tonight."
"What is your plan?"
"When we go to bed, I'm going to get her all worked up and perhaps even a bit tied up. We've talked about doing that for a while, and we haven't done too much in a few days."
"So what do I do?"
"If it works out like I plan, I'll hang a pair of panties on the door when we go to bed. That will be the signal that we're on, and I'll come get you when the time is right."
"Are you still sure that this is going to be ok?"
"Really sure Jason. Trish really wants to, she just talks about it all the time and when she does, she gets so turned on and cums so hard. Trust me...it'll be great."