Boston Road Trip Ch. 02

Once Mary was done in the bathroom, I took my turn and was still almost ready to go before the two of them were. We left Mary's apartment and spent many hours out and about around Boston, seeing the sites and enjoying the local cuisine and beer scene. It was a long day that ended with us hanging out in Mary's apartment with some carry-out and some local brews, just kicking back, relaxing and enjoying each other's company. Debbie and I hadn't determined what time we'd be leaving the following day but we definitely didn't want to be tired and hungover so we didn't stay up too late or get too drunk. When we finally decided to call it a night, I was starting to think about seeing Debbie naked and fucking her then sleeping for a few hours before fucking Mary.

We all did our nightly ablutions and, when I had a private moment with Debbie, I told her that I'd listen for Mary to go to sleep and keep her updated via text so she wouldn't worry that I'd fallen asleep instead. When I had a private moment with Mary, I confirmed with her what time I'd set my alarm for and that she was good with that time. I'd figured on about thirty minutes for her to fall asleep then an hour with Debbie followed by a few hours of sleep while also allowing for a few hours of sleep afterward. She was fine with the time I proposed and hoped she'd be able to sleep until then. I hoped so, too.

When they each went to their respective bedrooms, I turned out the lights in the living room and waited patiently. Debbie and I texted back and forth a few times and I checked and double-checked my alarm but mostly I just listened. Eventually, I actually heard Mary snoring, which I figured was about the best sign I could get that she was asleep. I texted Debbie and crept softly to her bedroom door. It opened quietly and I was pleased to see a lamp still on, illuminating that she was lying in bed with the covers pulled up just over her nipples so that I could tell she was at least topless under them. I stood at the foot of the bed and slowly pulled the covers down, revealing her succulent tits first then, eventually, her trim bush. As my cock grew harder, I realized my phone was still in my hand so I took a couple of quick photos before moving to the side of the bed with my shorts tented out. Debbie reached out to stroke the bulge as I set my phone down and picked up the condom that she'd set out.

As I was tearing open the condom wrapper, Debbie rolled toward me to pull my shorts down and, while I stared at her tits moving around, my cock sprung out as her focus was on it. I managed to get the condom out of the wrapper in spite of the distraction and, after she briefly stroked my cock, I rolled it on. She positioned herself on her back with her legs spread so I just climbed up on the bed on my knees with my sheathed cock bouncing in front of me. After taking a moment to admire her naked body before me, I lowered myself over her and guided my throbbing cock into her. We both moaned softly as I slipped inside then I brought my lips to hers as I started to slowly fuck her. Her pussy felt amazingly snug and slippery so I was glad for the condom to help delay an inevitably quick orgasm. As hot and wet as her pussy was, I suspected that she might be well on her way, as well.

As much as I had enjoyed her visit the previous night, I liked the feel of her naked body below me and her tits pressing against my chest. Despite this, I didn't expect that missionary was going to end up being our go-to position; I also wanted to see her tits bouncing above me or her ass jiggling as my hips tapped against it. After a long, busy day, however, feeling our bodies pressed together as our tongues explored each other's mouths was perfect. The bed remained quiet even as I gradually increased my pace and fucked her harder. She was raising her hips to accept my incoming thrusts and eventually pulled her mouth from mine and pressed her face against my neck. I could tell that she was holding back moans and was pleased that she was feeling so much pleasure. Her pussy sure felt fantastic through the condom and I would have been fine filling the condom with my load but, if she came before I did, I had another plan.

I was glad that she was moving more quickly toward her orgasm than I was toward mine. I knew that I had to be careful about staying with her for too long, lest Mary discover that I was not on the couch if she got up, but there was no way I'd be able to resist a certain opportunity if it presented itself. I was confident that it wouldn't require me to be in there much longer than if I just continued fucking her until I spewed into the condom, anyway. Debbie must have been lying there, naked and waiting for me, thinking about what was going to happen once Mary was asleep because it wasn't long before she was tensing up in advance of cumming and I knew that I wasn't solely responsible for getting her there so quickly.

Finally, with a soft squeak that she apparently couldn't hold in, her body started trembling as she was cumming. Her pussy felt as though it was flooded with even more lubrication so, as I continued fucking her, I could feel my own orgasm continuing to build up. Her orgasm, once again, appeared to be long and intense which made me glad that she didn't seem to have any issue achieving them. Again, I did not feel solely responsible for her ability to cum easily and strongly. I continued fucking her at the same steady pace until she went still and let out a shaky sigh. At that point, I gave her a quick kiss before slipping my cock out of her and moving up to straddle her, slipping the condom off as I did. I lay my throbbing cock between her tits and, as she gazed at it, I squeezed her tits together around it. I started to slowly fuck her tits, relishing the pleasurable feeling provided by the soft, smooth, warm flesh.

I realized immediately that there was going to be no issue with me being in with Debbie for too long; my orgasm was building again quickly as I fucked her luscious tits. Her focus was on my cockhead as it appeared repeatedly from between her tits, pointing at her face. As worked up as I was, there was a good chance that I'd have some pressure built up behind my orgasm though it wasn't necessarily a goal at that point to spew on her face or into her mouth. I was just savoring the building pleasure and the sensation of her tits against my cock. I had no doubt that this would not be my only opportunity to fuck her big beauties but the first time was undoubtedly going to be the sweetest. The pleasure I was feeling almost caused me to close my eyes but I couldn't resist looking down at her freckled chest, large areolas and thick nipples. When I finally started spewing, I certainly wasn't taken by surprise, but her eyes went wide and she stuck out her tongue, which I did manage to hit. My first couple of spurts hit her chin, lips and tongue but the rest of my jizz pooled on her chest.

I continued fucking her tits until I was too soft then only reluctantly released her tits and moved off beside her. She was spreading my cum on her chest and licking it off her fingers as I knelt beside her and my gaze moved over her naked body. I was happy that she'd finally made a move and that I'd have a regular opportunity to enjoy not only seeing her naked but touching and licking and sucking and fucking her.

"You should probably go," she finally said.

"So now that you're done with me," I replied, "I'm dismissed?"

"Exactly," she said with a smile, "Get the fuck out already."

I smiled back then leaned down to kiss her before climbing off the bed and slipping back into my shorts. I looked over her naked body once more, fondled her tits then grabbed my phone and slipped out of the room. There was no way to know if Mary had been out of her room in the time I'd been with Debbie, but it still sounded like she was snoring softly so I thought maybe the odds were in our favor. I checked my alarm yet again, then crashed for a few hours on the couch. When my alarm went off, I had no trouble waking and I actually felt pretty good so I must have slept soundly. I sent Mary a quick text to confirm that she was awake and she responded immediately so I got up and quietly headed for her door. I slipped in and found her still wearing a nightshirt but lying on top of her covers with a lamp on her nightstand illuminated. I closed the door behind me then approached the side of her bed, sliding my hand along her thigh while pushing up the hem of her nightshirt. I was leaning down to kiss her as my fingers caressed her pussy and she reached out for the bulge in my shorts, which continued to grow as she massaged it. Her pussy was very wet and I knew I could just climb on top of her as I had with Debbie, but there was something I still hadn't done yet, for her or for me.

I climbed onto the bed, still wearing my shorts, and pushed her nightshirt further up, exposing her tits. I leaned down and licked and sucked her hard nipples before kissing my way down to her pussy. Lying on my stomach between her spread legs, I ran my tongue along her slit, tasting her pungent nectar. She started to moan then stopped herself but I was happy to hear her express her pleasure, however briefly. I assumed Debbie was probably sound asleep so I wasn't too worried about being heard but I was still thinking that it wouldn't be wise spend too much time with Mary. I had a feeling that, if Debbie was to find out or figure out that I was doing the same stuff with Mary that I was doing with her, not only would she be weird about it, but it might blow everything that I was expecting to happen once we were back in New Jersey.

I focused on making Mary cum quickly but with as much intense pleasure as possible. As I slipped a finger into her hot, wet pussy, I was also thinking that, the quicker she came, the sooner I'd be sliding my cock in there. I went to work licking and sucking her clit as I probed her pussy with my finger and she started writhing while reaching down to hold onto my head. As with Debbie, I assumed she'd been pretty worked up just thinking about what was going to happen before I even got there, so I would have been surprised if it took very long for her to cum. My cock was still rigid and I was thinking that, if she came and I started fucking her almost immediately, not only would her pussy feel incredible, but it was likely that she'd cum again pretty quickly, at least based on my previous experiences. She was holding my head, rocking her hips toward my face at an increasing pace so I kept doing what I was doing since it seemed to be having the desired effect.

I could tell she was close when she started tensing up and clamped my head between her thighs. Her pussy was so wet and engorged by this point that I wasn't sure she'd be cumming again quickly once I started fucking her because it might feel so good that I'd shoot my load immediately. Somehow she managed to stay quiet even when she suddenly went limp and her body started shaking. I continued to devour her as she was cumming, not raising my head until she'd gone completely still. At that point, I was quickly up on my knees, pushing my shorts down to free my cock, which I then guided into her as I lowered myself over her. She gasped softly as my cock filled her and I started to slowly slide it in and out.

Her pussy felt amazing and I was relishing the opportunity to fuck her again. I wasn't sure whether we'd have an opportunity while Debbie was showering the next morning, so I was completely tuned in to every sensation I was experiencing, not knowing if I'd have a chance to feel any of them again, at least with Mary. When I had a good rhythm going, I brought my lips to hers and we started making out as we were fucking. Her bed, like her daughter's, was sturdy and well-built enough that it remained silent as I was thrusting into her, fairly vigorously. While I was hoping that she'd cum again, I wasn't trying to hold off myself by any means. I could feel my orgasm building from the moment I'd slipped into her, just as I'd expected, because her pussy felt so incredible. Of course, I wasn't really in a hurry to be done, either; I wasn't even thinking about Debbie possibly figuring things out right at that moment. I wanted to feel the pleasure continue to build for as long as possible before I came and, hopefully, she came, too.

When she pulled her mouth away from mine and pressed her face into my neck, I was thinking that maybe she was getting close but that didn't change the way I was doing things. Her pussy was feeling even wetter and more slippery so I could feel my orgasm building up even faster because it felt so good. Fortunately, the reason for this was that she was right on the verge of cumming again, just as I'd hoped. When she gasped softly and her body started shaking below me, I both pleased and relieved that she'd cum again. I continued thrusting into her, relishing the increased lubrication and the building pleasure. I think she was just coming down when I grunted softly and started spewing into her. I kept thrusting with each spurt, holding back a moan because it felt so damn good. I continued fucking her even once I was spent until I got too soft to continue. I moved off and lay beside her, looking over her naked body as she was catching her breath.

"I wanted to suck your cock again," she finally said, "but I'll have to take care of that during Debbie's shower."

"I will be ready to go again by then," I promised.

"I wish you could sleep in here with me," she lamented, "It's been so long since I've had a guy spend the night."

"That would be nice," I replied, "Probably not worth the awkwardness of the drive home if Debbie was to find out, though."

"True," she said, "so you should probably get back to the couch in case she has to pee or something."

I'd never completely shed my shorts, so I just pulled them back up and climbed off the bed, giving her one last kiss as she pulled her nightshirt down to cover her nakedness. I slipped out of her bedroom and crashed as soon as I hit the couch. As with the previous morning, I was out even as the two of them got up and made coffee. I gradually awoke with the brightening morning and the low murmur of their conversation in the kitchen. I eventually awakened enough to drag myself to the bathroom then joined them in the kitchen, pouring myself coffee before joining the conversation. There was not really a discussion of the day's plans since Debbie and I would be leaving before noon but we talked about how fun it had been. Eventually, I recalled that Mary had promised to blow me before we left so I was ready for Debbie to go hit the shower. I think Mary was, too, but hopefully our subtle prodding was subtle enough. When Debbie had gathered her things and had closed the bathroom door, Mary and I moved from the kitchen to the couch, where she caressed my cock through my shorts until the shower turned on. As she was sliding my shorts down, I encouraged her to straddle my head as I lay on the couch. I pushed her nightshirt up as she positioned her pussy above my face then, as she engulfed my cock in her mouth, I started to lick her slit, finding it overflowing with juices.

With time being of the essence once again, I soon had my finger sliding in and out of her pussy as I licked and sucked her clit. I don't know how much she was focused on her own pleasure since she'd originally just wanted to suck my cock but I had to believe that sucking my cock was getting her pretty worked up in addition to my actions. I didn't expect to have any issue cumming before Debbie was done in the bathroom because Mary's cocksucking had my orgasm building up pretty quickly, even though some of my focus was on her pleasure. It didn't seem like she was going to have any issue, either, because I could feel her pussy becoming wetter and more engorged around my finger. She actually ended up surprising me because I had no idea when she was right on the verge of cumming and suddenly she started shaking. She never stopped sucking my cock but I could tell that she was having an orgasm.

When she'd finished cumming, she actually moved off of the couch to kneel beside it and continued blowing me; I guess she didn't want to be distracted. I lay there watching as her lips slipped up and down my shaft, relishing the pleasurable feeling. She was doing a commendable job of bringing on my orgasm and my cock was soon swelling even more. This didn't throw her off at all as she seemed entirely focused on savoring the thick cock in her mouth. Finally, I started spewing into her mouth with an audible grunt since I knew Debbie wouldn't hear in the shower. Mary swallowed my load and continued sucking me off. I spurted a few more times before I was spent and she let my cock fall from her mouth when I had nothing left. She looked up at me and smiled.

"Thanks," she said, "I'll be thinking about that for a while."

"Shoot some video of yourself if thinking about it leads to anything," I suggested, "I'll reciprocate."

"Okay," she replied, "that could be fun."

By the time Debbie exited the bathroom and went into the bedroom she was using, Mary was in her bedroom and I was sitting there, looking at the photos of Debbie from the previous night and the ones Mary had just allowed me to take moments earlier. Even with that, there was no way I'd be able to get it up again if Debbie wanted a little before we left. I'd have to put her off with the promise of driving orgasms followed by a night at her place once we were back in NJ. As it turned out, by the time she was done getting herself together, it would have been too late, anyway, though I suspect she was also thinking that we'd have more time and freedom when we were back in NJ so there was no need to squeeze in a quickie. We were sitting on the couch chatting when Mary was done in the bathroom which I thought looked good for keeping Mary from getting suspicious.

When I was done in the bathroom, dressed and packed up, we headed out for breakfast before Debbie and I had to hit the road. Once we'd finished, there were a lot of hugs and promises that we'd see each other again very soon then Debbie and I had to be on our way. She navigated me out of the city and back onto the highway but it wasn't until we were out of traffic and on the open road before she reached over to caress my cock. By then, I'd had plenty of recovery time so my cock immediately stiffened.

"Can you do me a favor?" I asked as she was extracting my rigid cock.

"I thought I already was," she replied, pumping my cock in her fist.

"No, that's so I'll drive you home, remember?" I said, "Equal trade. This is above and beyond that."

"Okay, sure," she replied, "what else can I do for you?"

"Can I have you pull the top of your sundress down?" I asked.

"Do you promise not to crash?" she asked in return.

"I absolutely promise not only not to crash," I replied, "but to make sure you cum in return."

"Sounds like a deal," she said, releasing my cock and reaching for the bow behind her neck that was responsible for keeping her tits covered. I kept my focus on the road until she pulled her top down and her luscious tits were freed, since she had no bra on underneath. I kept alternately glancing over until she reached over to help slide my shorts and underwear down, bringing her tits close enough to fondle. As she leaned over to take my throbbing cock in her mouth, her left tit was hanging right there, so I cupped it and hefted its substantial weight. As she wrapped her mouth around my cock, I moaned loudly because I finally could and because it felt fantastic. I had one hand on the wheel and one hand on her tit and could feel my orgasm beginning to build as she put her oral talents to work on my cock.

I had the cruise control set and the traffic was fairly light so I didn't need to be intensely focused and could appreciate the feel of Debbie's mouth moving up and down my tool while she gently pumped the base. I was definitely going to love a future that involved a lot of blowjobs from her, though I also anticipated eating her pussy a lot, and fucking her tits and having sex without worrying about being discovered. Thinking about undressing her and showering with her and just laying around in bed with her had my orgasm building even faster. She definitely seemed more self-assured on this drive than she had on the way up. Not that the first blowjob was not good but it just felt like she was more confident that we were on the same page and was able to focus on deploying her skills. I was loving every second of it.