Boston Road Trip Ch. 01

Conversation gradually involved me as Mary brought up potential plans for the day and we made some decisions about what to do. Once we had that figured out, Mary suggested that Debbie take the first shower, joking that she'd take the longest to get done. Debbie disputed that but didn't turn down the opportunity. She went to grab some things then headed for the bathroom. As soon as she'd closed the door, Mary was massaging my cock through my shorts, causing it to rapidly stiffen. Once she heard the water running, she started to slide my shorts down, releasing my throbbing tool. She straddled me on her kitchen chair, raising her nightshirt and giving me my first look at her trim, light brown bush. She sat down on my cock, moaning a bit louder than she had earlier that morning on the couch, and started riding it right away. My hands were on her bare waist under her nightshirt as she lowered herself onto my cock but I moved them around to caress her ass as she started to ride me.

Her pussy was as hot and wet as it had been the previous night so I wondered if she'd been anticipating fucking me the entire time we'd been sitting there or just since Debbie had left the kitchen. Either way, feeling it sliding up and down my cock was pretty awesome once again and, though I suspected she was probably well on her way to an orgasm, I knew it wouldn't take much before I was ready to spew deep into her pussy. We tried making out a little bit but she was riding me too hard and fast and I guess she decided that was more important than having her tongue in my mouth. My hands eventually gravitated up from her ass to her bare tits, which were bouncing under her nightshirt. I caressed the soft, smooth flesh and her hard nipples, which may have helped her level of arousal more than my hands on her ass. She had her eyes closed and a look on her face that indicated high levels of pleasure. Even with all that, I was still surprised that she started cumming so quickly after she'd started riding my cock.

She dropped down and remained there as her entire body trembled and her expression showed what appeared to be ecstasy. I continued fondling her tits, wanting to savor the opportunity since I wouldn't have it after the following day. My cock was still rigid as she finished cumming and just sat on it, catching her breath. I knew Debbie wouldn't be in the bathroom forever so, after giving Mary a couple of minutes, I had her climb off of my cock. I turned her around and had her bend over, resting her head on her arms on the kitchen table. I pushed her nightshirt up to her shoulder blades then slipped my cock into her from behind. I held her hips and pushed until my hips were touching her ass, then started fucking her. She was immediately pushing back and slipped a hand back between her legs, presumably to massage her clit. We got a good, fast rhythm going and I could immediately feel my orgasm building up. Fucking her felt awesome and I knew I would still be thinking about it after I was back in New Jersey.

I didn't do anything to try to prolong fucking her, mainly because I wanted to make sure I was able to cum before Debbie finished in the bathroom. I was watching her ass jiggle each time my hips tapped against it when it occurred to me that her tits were probably swinging like crazy, so I reached forward to cup them. Again, I don't know if fondling her tits brought her any closer to orgasm but I think it actually did help push me along. Maybe my hands on her tits made her pussy even hotter and wetter or just feeling them made my cock even harder but I was certainly relishing the position I was in and what I was feeling. Had Debbie walked out of the bathroom and into the kitchen at that moment, there's no way I would have even tried stopping. Luckily, it didn't come to that.

I was pleasantly surprised when Mary gasped and her body started shaking again. As she was cumming, her pussy was flooded with even more lubrication and I felt my cock swelling even more as I approached my own orgasm. I ended up straightening up and taking her by the hips so I could fuck her even harder, my hips now smacking against her ass. When she finished cumming, she started pushing back into my thrusts and it didn't take but a moment longer before I was spewing into her with a moan. I continued thrusting as I continued spurting until I was completely spent and had nothing left. I slipped my cock out of her and she straightened up, immediately grabbing a napkin from the table and holding it between her legs to catch the cum that started running out. I grabbed a napkin myself to wipe down my cock, then tossed it in the trash and pulled up my shorts. She discarded her napkin as well and I took her in my arms and we made out for a moment.

"I'm definitely coming to visit you tonight," I finally said when we parted.

"I can't even remember the last time I got fucked in my bed," she replied.

"Well I hope it doesn't make any noise," I said, "but just to play it safe, I'm going to set an alarm on my phone instead of laying around waiting for Debbie to fall asleep."

"Good idea," she replied, "I'll keep my phone next to my bed and you can let me know if the coast is clear and you're on your way."

"Okay," I said, "and when we go to bed, I'll let you know what time I'm setting my alarm for."

"Perfect," she replied, "I can't wait, but I'd better get ready for my turn in the shower."

I grabbed another cup of coffee and went to sit on the couch, pulling together what I would need for my shower then checking a few things on my phone, like how to set an alarm. When Debbie exited the bathroom, she went right into Mary's daughter's bedroom and closed the door. Once Mary was in the shower, I considered going to pay her a visit but I didn't think I'd be able to get it up again so soon, even if Debbie was naked. We didn't have the time to have to work for it and I didn't want her to get suspicious, so I just remained on the couch. Eventually, she came out fully dressed and with her makeup and hair done. She walked over and handed me a condom.

"For your wallet," she said with a smile.

"Maybe you should just keep it by the bed," I suggested, "I expect that I'll need it later."

"Oh, I've got more in there," she replied.

"You were planning to get laid quite a bit this weekend?" I asked.

"Actually, I was planning to finally put a move on you this weekend," she confessed, "I resolved to push past my fear of rejection."

"Well, to be honest," I told her, "I'd have done it myself but I was concerned that I'd just make things awkward if I did and you weren't interested."

"Do you think things will be awkward?" she asked.

"No," I replied, "not with both of us so into it. What made you decide this trip would be the best time to initiate something?"

"Well, it wasn't like I consciously decided to do it during this trip," she said, "it's just that I finally actually got the balls to do it."

"I'm glad you did," I told her, leaning closer to give her a kiss. We made out for a moment.

"If I'd been thinking at all, though," she said, "I'd also have jumped you while Mary's been in the shower. I guess it's a little late now."

"Oh, don't worry about that," I assured her, "we'll have plenty of opportunity once we're back in Jersey and I was planning on coming to visit you tonight, anyway."

"Can you do me one favor, though?" she asked, "Can we not let Mary know what's going on? I just think she might be a little weird about it."

"No, absolutely," I replied, "I will defer to your judgement on that but I'm fine with it."

We kissed a little bit more then I tucked the condom in my wallet and she went to finish getting ready.

To be continued...