Boston Road Trip Ch. 01

We were expecting to be on the road for about five hours as we headed from New Jersey up to visit Mary outside of Boston. I was driving and Debbie was my navigator. She'd offered to split the driving with me but I was fine with taking on the entire thing. Debbie really appreciated that and ended up making sure to let me know just how much. We were a couple of hours into the trip when she'd asked if I wanted her to drive and I'd told her it wasn't necessary.

"Well, the least I can do," she said, "is make the drive a bit more enjoyable for you."

She reached over and started to caress my cock through my shorts and, of course, it immediately started to stiffen. We had never so much as kissed before and, although we'd known each other for ages, we'd only recently become closer friends. I had thought plenty about how she'd look naked and what it would be like to fuck her but I didn't really want to date her so I had held off on making any overtures. I had no complaints when she took the initiative. Once she felt my cock growing rigid, she opened my shorts then slid them down along with my underwear. She stroked my throbbing tool before positioning herself so that she could lower her head into my lap. As she engulfed my cock in her hot mouth, I moaned due to the pleasurable feeling but did my best to remain more focused on driving.

She started out slowly sliding her mouth up and down my tool, which felt absolutely amazing, but she did stop to stroke it occasionally and also would caress or lick my balls. It had been a while since I'd had any action aside from my hand so I was relishing this unexpected blowjob but not expecting it to last very long. I think only the fact that I had to be somewhat focused on driving kept me from cumming immediately. Her cocksucking left nothing to be desired and I was hoping that, from this point forward, I would have many opportunities to enjoy it. Since Mary lived in a small apartment with her daughter, I didn't think we'd have any opportunity to take things further until we were back in New Jersey.

Debbie had a really nice set of tits that I'd thought many times about how nice it would be to see them, get my hands on them and fuck them. At least one of those things I could accomplish while I was driving so I reached under her to cup her hanging tit. It was restrained by her bra and her dress but I could still feel her hard nipple pressing out and that made me wonder if sucking my cock had her pussy wet. I was pretty confident that I could make her cum while I was driving even if I was limited to using my fingers rather than my tongue. Thinking about her tits and her wet pussy had my cock growing even thicker as it pushed me even closer to an orgasm. She remained focused, though, just as I remained focused on keeping the car between the lines even though I wanted to lean back and close my eyes. Fortunately, we were on a pretty straight, not very busy section of highway so I had the cruise control on. If I hadn't, I think I may have stomped on the gas as I started spurting into her mouth with a groan. She swallowed my load and continued to suck me off until I was completely spent, then let my cock fall from her mouth and straightened up, moving to reseat herself.

"We're going to have to take a lot of road trips," I said, "That was outstanding."

"You don't have to be driving for me to do that," she confessed, "but I just figured you'd have a tougher time pushing me away."

"I had no desire to push you away," I assured her, "and will absolutely be returning the favor as soon as I can. In the meantime, I will take care of you the only way I can at this point."

I reached over and placed my hand on her thigh then slid it up along with the hem of her sundress. Not only didn't she resist, but she spread her legs as she made herself more comfortable. When my hand reached her panties, I massaged the front of them before slipping my hand inside. Her bush was trim and I could feel the blood trying to return to my spent cock as my fingers passed through it. I found her pussy overflowing with juices as I'd anticipated and easily slipped a finger inside her. She moaned softly as I slid my finger in and out a few times before focusing on gently caressing her clit. I glanced over, seeing that her eyes were closed and her mouth hung open as moans continued to slip out. I couldn't see anything else indicating what was going on except when I quickly glanced downward to see her exposed panties with my hand writhing about within them.

Once again, the blood wanted to return to my flaccid cock as I forced my gaze away from her panties while I continued to alternately caress her clit and slide my finger in and out of her hot, wet pussy. It wasn't affecting my ability to drive so I'd have been more than happy to continue for the remainder of the trip but I could feel her pussy becoming even wetter and more engorged each time I slipped my finger into her. She was also rocking her hips and moaning more continuously so I knew that she was approaching an orgasm. I was happy to be able to provide her with such pleasure, especially since she'd put herself out there initially, though I can't imagine she really thought I'd have turned down a blowjob. I didn't try to get her there any faster once I knew she was on the verge; I just kept up what I'd been doing since it seemed to be working just fine. She gasped just as her body started shaking and I glanced over again to see the look of passion on her face. I kept going as she rode out what appeared to be a long and intense orgasm, stopping only once she'd let out a long sigh. At that point I reluctantly slipped my hand out of her panties and slipped my finger into my mouth, tasting her pungent nectar.

"It's been too long since somebody besides me has taken care of that for me," she finally said.

"I was thinking the same thing about you," I replied, "Why has it taken this long for us to realize that we could have been helping each other out?"

"I guess rather than lament the opportunities we didn't take," she pointed out, "we should just make sure we don't let any other opportunities slip by."

"Good point," I responded, "so as soon as I can get my face between your thighs, instead of my fingers, I going to give you a hell of a licking."

"Ooh," she replied, "I can't wait, but maybe we should get you tucked away for now."

She held the wheel as I got my shorts back in place and fastened up. I took over the wheel again and, while we went on chatting, I wondered if maybe there actually would be an opportunity for something while we were visiting Mary. I didn't really want to wait until we were back in New Jersey but I also didn't think it would be cool if we got caught in the act, especially if it was by Mary's young daughter. The closer we got, though, the more excited we were about seeing Mary and spending a couple of nights with her, even if it meant going hands off until we left. Debbie navigated us right into Mary's neighborhood and we managed to find parking not far from the house where she rented her small apartment. She was thrilled to see us and we were surprised to find that her daughter's dad had agreed to take her for the weekend. We were just a little disappointed not to see her but knew that, if she was out of the picture, things could get just a little more wild.

We started that night with a couple of drinks at Mary's apartment as we unwound from the long drive. Once we were loosened up a bit, we headed out for dinner, followed by more drinks at a local bar. We were feeling pretty good once we called it a night but had consciously refrained from getting shitfaced so that we could enjoy a full Saturday together rather spending half of it recovering. With Mary's daughter gone, Debbie was able to take her bedroom while I took the couch, which I didn't mind at all. I definitely didn't fall asleep immediately as I thought about what had happened on the drive up. I don't know how long I'd been lying there but I'd reached a point where I was considering whether to get up and pay Debbie a visit. The question wasn't whether she'd have an issue with being awakened but whether I could get in there, presumably fuck her and get back to the couch without Mary being aware of what was going on. As I lay there overthinking it, Debbie just came out and knelt beside the couch.

"Oh good, you're awake," she whispered.

"I was thinking about having sex with you," I replied.

"Well you can stop just thinking about it," she said, "but first there's the small matter of something you promised."

She stood up and straddled my face on the couch while raising the hem of her nightshirt. She had no panties on and I could see her trim bush in the dim light filtering through the blinds. As she brought her pussy close to my face, I reached up and gripped her ass cheeks then ran my tongue along her slit. She made a soft noise that sounded like she was biting back a moan that tried to slip out. I lapped at her pussy, tasting the abundant juices that she was producing as I felt my cock becoming rigid in my shorts. Since I knew the longer we spent, the greater the chances were of Mary walking in on us if she had to visit the bathroom or something, I focused all of my energy on making Debbie cum. I brought a hand down from her ass and slipped a finger into her pussy, once again finding it incredibly hot and wet. As I was sliding my finger in and out, I was licking and sucking her clit as she subtly rocked her hips toward my face.

Obviously I didn't know her body well enough yet to be confident that she was quickly building up to an orgasm, but it sure seemed like it. If she'd been lying in bed thinking about coming out and had gotten herself worked up enough to actually do it, I presumed that she could be even further along than she'd been in the car. Of course I didn't necessarily want to just be done eating her but I knew there would be better situations to indulge myself and I definitely wanted to slip my cock into her still, so I didn't mind at all if she came quickly. Her breathing was the only thing I was hearing inside the apartment and the way it sounded, along with how her pussy was feeling, helped clue me in when she was right on the verge. Fortunately, when she did start cumming, she didn't cry out or moan loudly. I could feel her body trembling and she did sort of quietly gasp which was enough to let me know. I continued what I was doing and her orgasm seemed to be even longer than the one she'd had in the car. Once she'd apparently finished cumming, she climbed off of my face and knelt beside the couch again.

"That was fantastic," she whispered, "You're very good at that."

"Well any time you want," I replied, "I'd be happy to do it again."

"I will definitely be taking you up on that," she said, "but for now, do you have a condom?"

"In my wallet," I replied, "behind you."

She turned and grabbed my wallet then handed it to me. I removed the condom and she replaced my wallet on the coffee table then took my shorts down, my cock springing out. She got up and, as she was straddling me, I tore open the condom and rolled it on. She lowered herself onto my cock and we both moaned softly. Her pussy felt incredible, even through the latex. She sat on my cock for a moment as I relished the snug, hot, slick feel of being embedded in her. As she started to slowly move up and down on my cock, I slid the hem of her nightshirt up, first so that I could gaze at her trim bush then so I could get my hands on her bare tits. I raised the hem up high enough to expose her tits so I could get a good look at them and just watched them bounce for a moment as she moved up and down on my cock. Finally, I reached out to caress the soft, smooth, freckled flesh and I think my cock actually got harder as I did.

I couldn't believe I was finally seeing and fondling her succulent tits and I think that may have been the only thing that prevented me from cumming immediately. Because her pussy felt so outstanding, I felt my orgasm beginning to build up as soon as she started riding my cock but, while I was absolutely enjoying and appreciating it, dividing my attention between that and revealing her tits helped me hold out to enjoy it longer. I was thinking about how there was going to be some titfucking and nipple sucking in the future and, though I was still just envisioning how she'd look totally naked, I knew I'd see for myself soon enough. I didn't know if my fondling her tits was helping her along at all but as I passed my palms over her hard, thick nipples, I had to think that it couldn't hurt.

I was listening to her breathing again and looked up from her tits to her face to see that passionate expression again, which I hoped meant that she was almost there because I was pretty close myself. I started pushing up into her as she came down on my cock, not because I necessarily wanted to cum faster, but I wanted to try to make sure she came again. I could feel my cock swelling even more as I was right on the verge of cumming and, whether it was that or something else that caused it, I was relieved when I felt her body trembling. Her pussy was flooded with even more lubrication as she came so, before she'd even finished, I was blowing my load into the reservoir tip of the condom. We had nearly simultaneous orgasms and it was pretty fucking awesome.

She continued riding me until we were both spent then climbed off of my softening cock. She knelt beside the couch again and we made out briefly as I fondled her tits through her nightshirt. She finally took the condom off and also grabbed the wrapper.

"I'll flush these," she whispered, "I hope she's got some decent water pressure."

She gave me another kiss then headed into the bathroom. I didn't pull my shorts up right away because my cock was sticky with fluids and I didn't want to stain the front of my shorts. I waited until Debbie had exited the bathroom and returned to bed then went to the bathroom myself, to pee as well as to clean myself up. Once I was back on the couch, I was rehashing what had just happened but didn't get far before I was asleep. I think I managed to get at least a couple of hours before I was awakened again. I felt a hand slipping into my shorts and stroking my growing cock as I thought that Debbie had to be really horny to be back again. I was still waking up as I felt my shorts slide down then a warm mouth engulfing my cock, which continued to stiffen. When I finally opened my eyes and looked, I was surprised to see, not Debbie, but Mary sucking my cock. When she realized I was awake, she slipped my now rigid cock from her mouth.

"I can't even tell you how long it has been since I had a cock in my apartment," she whispered, "much less in my mouth. I really want to get fucked, though, if you're okay with that."

"Do you have a condom?" I asked.

"Well, ironically, even though I'm not getting laid," she replied, "I have been on birth control since my daughter was born so we're good."

She had me sit up and took my shorts down to my ankles then straddled me and guided my cock to her pussy. She wasn't as snug as Debbie had been but her pussy still felt outstanding, especially without a layer of latex. I slipped my hands around to caress her ass as she started moving slowly up and down on my cock. Like Debbie, I'd also had plenty of thoughts about fucking Mary and even thought it might be possible for something like this to happen but, once Debbie had blown me in the car, I'd pretty much forgotten all about the possibility. I figured there was no way I'd have two women who wanted to fuck me at the same time. As I brought my hands up from Mary's ass to fondle her tits, I was well aware that I wasn't dreaming and knew this might be my only opportunity to fuck her so I planned to savor it. She was wearing a nightshirt so I slipped my hands up the front and caressed the soft, smooth flesh of her tits. They weren't nearly as big as Debbie's so her nipples, though also hard, weren't so thick. I still wanted to see her naked, too, but this wasn't going to be the time.

I was less concerned about Debbie getting up since I knew she'd visited the bathroom earlier but I still didn't want to be interrupted. I also thought, since I'd cum twice already, that I might be able to hold out longer even without a condom. Given that she started blowing me before she knew I was awake, I suspected that Mary was likely very fired up and it might not take much before she was cumming. She had her hands on the back of the couch behind me and it didn't take long before she was riding me harder and faster. I just let her control the pace while I fondled her tits and savored the pleasurable feeling of her pussy sliding up and down my tool.

When I was pretty sure that she was right on the verge, I wasn't quite there yet myself but I was sure that she'd take care of me one way or another. Her pussy was feeling even hotter and maybe a bit more snug as her breathing was almost gasping so, if she kept riding me after she came, it wouldn't take much longer before I filled her with my load. When her orgasm finally overtook her, she dropped down on my cock and sat there as her body shook and she gasped softly while trying to suppress any moaning. I just continued fondling her tits until she let out a sigh and climbed off of my lap. I wasn't worried about her leaving me hanging, especially when she knelt before me and engulfed my cock in her mouth again. I moaned softly as she blew me because her cocksucking skills left nothing to be desired.

As late as it was, and even though she'd already been satisfied, she put everything into that blowjob and I relished it and the pleasurable build-up of my orgasm. When Debbie had blown me while I was driving, I hadn't been able to fully focus on it being behind the wheel but, with Mary, I leaned back and closed my eyes and just savored it. Of course I didn't keep my eyes closed the entire time because there was enough light that I could watch as Mary's head moved up and down. I wanted to remember that visual and it was also so arousing that it was bringing my orgasm on even more quickly. When I had my eyes closed and I was just feeling the pleasure, however, my orgasm didn't seem to be coming on any more slowly. It was just two different levels of enjoyment.

As my cock swelled even more once I was on the verge of cumming, Mary's pace didn't even vary but I had to focus just a little on making sure I didn't cry out with the level of pleasure I was feeling. When I started shooting my load into her mouth, I gasped just a little but not loud enough for it to be heard by anyone but Mary and me. She swallowed my load and continued nursing my cock until it started to soften. She let it fall from her mouth then just remained where she was for a moment before standing.

"Thank you," she whispered, "I love sucking cock but let's keep this between us. I'm afraid it could make Debbie weird if she knew about it."

"Okay," I replied, "Good night."

She had already started walking back to her bedroom before I answered so I just pulled my shorts up and lay down. I was asleep this time before I had time to even reflect on what had just happened. I went down pretty deeply, too, because I never heard either of them get up later that morning. When I finally started to wake, I smelled coffee and could hear the murmur of a low conversation. My eyes gradually opened and there was a lot of sunlight coming into the apartment. I lay there as I awoke more and more and started to recall what had happened earlier on that couch. I suspected that the two of them were not talking about it but I wanted to make sure everything was committed to my long-term memory. As I continued to smell the coffee, I was eventually lured off the couch and upright and joined the two of them in Mary's small kitchen. They didn't seem surprised when I didn't say a word before going for the coffee but I really just wanted to see if they would continue their conversation or if I'd interrupted something they didn't want me to hear. I was relieved when they resumed conversing about some TV show they both watched.