Maggie May: jack_straw

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jack_straw
jack_straw
3,234 Followers

He handed me a small case, and I was stunned speechless, because I knew what it was. It was his competition-quality pool cue and he wanted me to take it with me on my trip.

"I suspect you're gonna be doing some hustling for cash," he said, his gruffness masking his emotions. "I'd rather you hustled with this than selling drugs. Take good care of it."

With that I took my leave, and it would be months before I darkened their door again. I would be a changed person when I did.

There were about a dozen or so in the group we traveled with. Maggie had, believe it or not, a vintage 1967 VW Microbus that she kept in pristine condition. We piled in the bus, and a couple of the guys rode Harleys. Needless to say, it was a pretty eclectic crowd.

One of the group that was traveling with us was an ex-biker that we called Easy Ed, and he was the mechanic in charge of keeping the machines going. He and I got to be really good friends, because we were the only ones with an interest in sports.

The first stop was Chicago, and that's where I first learned the inner workings of Tourheads. It was rare that we arrived at a venue with tickets in hand, so the first order of business was scamming a way into the show.

The next was raising funds, and we did that in several ways, one of which, regrettably, was selling LSD.

We also had one girl in the group who was adept at tie-dying T-shirts and designing art that she could transpose onto shirts and sweatshirts that we would sell in the parking lots.

The girls were also not above turning a trick or two, and I quickly learned that included Maggie. In fact, it would eventually come out that she was sort of the ringleader in that pursuit.

It kind of pissed me off, because I loved her (or thought I did), but what could I do? It was all a hustle, and she was only doing what she had to do for the group. Besides, we were just practicing a free-love mantra of the Sixties, weren't we? And I did end up fucking most of the other girls who were with us.

But that was just a small bit of unpleasantness in an otherwise blissful experience. The freedom was intoxicating, not to mention the plentiful drugs.

And I quickly became quite good at finding pool halls where I learned how to hustle. I'd take Easy Ed with me for back-up and we'd stroll in looking like out-of-place hippies.

At first, the real players wouldn't take me seriously, but after they saw my stick and after I started winning they'd sit up and take notice.

I soon got a feel for how far I could go before calling it a night, and I always left with some cash in hand, sometimes as much as $500 a pop.

From Chicago, we went to Cleveland, then Pittsburgh, DC (actually the University of Maryland), on to a run at Madison Square Garden, then to Boston and finally to Hartford.

A couple of the group wanted to go on and follow the band to Europe, where they were playing a few shows in London and Scotland, but Maggie and I both said no. I was Maggie's right-hand man, and usually what we said went.

We skipped the Dead's Eastern tour in May, but decided to hit the road again in the summer, when the band would make a Midwestern swing. That's when things started getting crazy.

There were some serious high times on that tour, but the one that stands out -- way out -- happened on the second stop. It was the Fourth of July, a Saturday night that year, at Austin, Texas, after we'd started the tour in Houston.

Actually, the show was at an old racetrack 15 miles or so outside of Austin at a place called Manor Downs. We pulled into the parking area early that day and Maggie and I set up the tent where we'd be sleeping.

By tacit agreement, we pitched our tent a little bit away from the vehicle, which was designated as Party Central. That gave us some privacy where we could fuck our brains out, or just crash, as the mood struck us.

It was hot that day, not quite as hot as it could have been, given that it was July deep in the heart of Texas. But it was hot enough, and across the road was a cattle pond that looked awfully inviting.

So Maggie and I decided to go over and join the crowd that was taking a dip. We just stripped and dove in. As we frolicked in the muddy -- but oh so cool -- water, I noticed this cute redhead chick with nice tits standing by herself in the water.

I was already tripping my nuts off, so my inhibitions were pretty low. I waded over to where she was and struck up a conversation.

Turned out she was a local, a student at UT named Barbara, and she'd come down with her girlfriends, except they'd chickened out from going skinny-dipping in what was admittedly a pretty rank body of water, and had walked back up to where they'd parked.

I figured out pretty quickly that she was looking for the whole Grateful Dead experience, so I asked her if she was looking for trips, and her eyes lit up. About that time Maggie waded over and I could see her checking out Barbara's very nice body.

I could feel myself getting hard as I watched Maggie giving Barbara the once-over. She'd never given me any indication that she was the least bit bisexual, but I could tell from the look in her eyes that she had designs on poor Barbara.

It shouldn't have been surprising that Barbara somehow never caught back up with her friends. We gave her a free, very liberal dose of the really top-notch acid we had with us, she stayed and partied with us, then she accompanied us to the show.

She was goggle-eyed as we made our way down to the front, where we watched the first set from about 10 yards from the stage.

During the break, I dragged her back to the concessions, where I literally got my first taste of fajitas, washed down with a cold Shiner's, then we somehow managed to make it all the way back to almost the same spot, where Maggie was patiently waiting for us.

Once we got back, Maggie fed us another dose of the liquid goodies, and we were off into the stratosphere.

During the second set, Maggie and I took turns dancing with Barbara, and running our hands all over her hot body. By then, Maggie and I had already cooked up what we were going to do with this girl once the show was over.

Afterward, we were still buzzing like crazy as we got back to the camping area. Barbara found her friends, and they were ready to head back to the city, and tried to talk her into leaving with them.

I know they were concerned about her safety, but she was still flying high as a kite and not ready to go home. I managed to mollify her friends with a promise that we wouldn't drag her off to Oklahoma City, where the next show was scheduled, and points beyond.

That done, we decided to go back to the cow pond. This time, I openly ogled Barbara's lush body. We sat in the water and kissed deeply, feeling the sexual tension mounting. Her soft hands found my rampant cock, while I filled my hands with her plump tits.


Just then, out of the corner of my eye, I saw a naked Maggie wading up to where we were making out.

"No fair," she said seductively. "You've gotta share."

Barbara gave Maggie a strange look. Me? I just stood up with my cock standing up proud and tall. I looked around and I saw several other couples writhing on the ground or even in the water in the throes of sex.

Maggie didn't fool around. She simply dropped to her knees in the muddy pond, wrapped a hand around my dick and worked it between her lips. She lashed her tongue around the shaft as she slowly jacked me to a feeling of bursting.

Before she got it past her lips, Maggie backed her face off and turned my cock toward Barbara, who was still sitting in the water watching. She climbed up on her knees and took the proffered cock and slid it right into her mouth.

I groaned as Barbara's hot mouth engulfed my throbbing cock, and I wrapped my hands in her thick auburn hair to keep some measure of control. As I did, I stared at Maggie, and the look in her eyes sent chills of lust up and down my spine.

Barbara gave pretty good head, and I could see a competition developing as Maggie none-to-subtly pulled my cock from Barbara and took every bit of me into her mouth, to the point where I was poking at the entrance to her throat.

Not to be left out, Barbara fondled my balls and lightly sucked each one into her mouth while Maggie gave me a hum job for the ages.

Then she willingly relinquished my aching missile and let Barbara have at it again. As she did, I was jolted by the little strands of juice that connected my cock to her lips for just a second, before Barbara ravenously swallowed my cock whole, in one glorious suck.

I watched as Barbara's tits swayed gently in the warm night air, marking time with her oral skills. I could feel my cum boiling to the surface, and I made a snap decision.

"Come on, ladies, let's get out of this nasty hole and go back to the tent, where we can spread out," I said in a shaky voice.

This is how high we were. We just slipped our sandals on and walked naked back to the campsite. I had my arms around each girl's shoulder, and I felt like the King of Texas. All was right with my world at that moment, and if every day could have been like that, I'd have never gone back to the real world, never would have left Maggie behind.

What was really weird about it was that hardly anyone batted an eye. Oh a few people stared at us, or, more likely, stared at the two sets of tits that were jiggling seductively. But for the most part, it was just the most normal thing in the world to see three naked people walking through the camp.

That's what the sideshow that accompanied the Grateful Dead on tour was like.

It was a warm night as we crawled into the spacious tent that Maggie and I shared. We already had the sleeping bags laid out; all we had to do was spread out and get after it.

This time, it was Barbara's turn to get the double treatment. I latched onto her left breast while Maggie gave her a deep, sensual kiss. I had her hard pink nipple between my lips, but I was staring at the sight of two women kissing right in front of me.

I'd seen lesbians kissing each other before -- hell, I grew up in San Francisco, so I saw it all -- but never before had they been kissing for my benefit.

I reached down to stroke Barbara's pussy, and got a charge to find Maggie's hand was already there. So we both worked our fingers in her soupy pie as she writhed on the sleeping bag in mounting arousal.

As hard as my cock was, I wanted to see Maggie and Barbara together, so I just kind of nodded at Maggie, and she nodded back.

I climbed up on my knees while she slid in between Barbara's legs. I held the back of Barbara's head and offered her my cock to suck, and she devoured it like her last meal, then a muffled groan escaped her mouth as Maggie slid her tongue up her furrow.

I worked my cock in and out of Barbara's mouth, over her lips and even over her face, as the lust tried its best to consume me. All the time, I was watching Maggie expertly lick, suck and kiss Barbara's obviously twitching cunt.

Her back was arching in rampant pleasure as Maggie worked her magic on this willing young college girl.

About the time Barbara spit out a horrific orgasm, I pulled my cock away to give her free rein, and boy did she let it go. She was squealing and gasping, mewling and crying in the throes of her lust.

That was my cue.

I was like a Viking in a berserker rage. I pulled Maggie's head away from Barbara's super-hot pussy, knelt between her legs and plunged in balls-deep on the first thrust. Barbara just wailed that much louder as I put the pipe to her hard and fast right from the first stroke.

Maggie was also in the grip of her own lust, and she didn't hesitate, but knee-walked her way up the pallet, straddled Barbara's head and dropped her dripping pussy onto the startled redhead's mouth.

I can't say we raped the poor girl, but we sure didn't give her any time to think about what we were doing; we just plunged ahead, oblivious to anything but our own pleasure.

As it was, she was so high and so horny, we could have probably brought the entire Longhorn marching band in there and she'd have been willing to take them on.

All I knew at that moment was that I was fucking some very prime pussy and watching my girlfriend grinding her crotch on a pretty young face. Doesn't get much better than that.

Maggie threw her dark hair back and swayed in passion as Barbara worked her lips and tongue on her smoking pussy. I could hear wet muffled groans as Barbara feasted on Maggie.

I had my hands firmly on Barbara's hips as I plowed my cock relentlessly in her spastic cunt. I was teetering on the brink, I could see Maggie was right on the edge and I could sense that Barbara was getting close as well, from the convulsions of her body.

I tried to hold it off as long as I could, but when Barbara pulled her face out from under Maggie's pussy and screamed for me to, "fuck her harder, harder, harder," that finished me.

I cut loose with a rapid rocket load of molten-hot cum, deep in Barbara's twitching, clenching cunt. I looked up to see Maggie frantically fingering her clit as she shook with her own climax. I just kept humping my cock back and forth, back and forth in a seemingly endless barrage of orgasmic twitters, until I finally had nothing left to give.

I fell back on my haunches, my sated cock flopping wetly from Barbara's dilated hole, and that's when Maggie went over the edge.

She leaned over, grabbed Barbara's butt and buried her face in the redhead's overflowing pussy. I watched as Maggie lapped up everything I'd deposited in there seconds earlier, and she and Barbara just kept right on going, in a sizzling-hot 69 that had my cock roaring again in no time.

I mean, it was obvious these gals were swinging for the fences on this night, and I wasn't going to be left behind. Fortunately, I'd ingested enough acid that it didn't take much to get my cock back up to speed.

Just to make sure, though, I pulled on Maggie's hair to left up her head, and slid my cock into her voracious mouth. There was an other-worldly glow on her face as she sucked my rampant cock as I just stared at her.

When I was sufficiently hard, I crawled back around, got behind Maggie's butt and pushed my cock into her pliant depths. As I did, I felt a warm wetness around my balls as Barbara gently sucked each testicle, sending lustful sparks flying.

Sweat covered our bodies as I fucked Maggie from behind, while Maggie's mouth sent Barbara into orgasmic delight again and again, and while Barbara tried her best to keep up.

I could finally feel my control slipping, so I picked up speed, then plunged deep in Maggie's experienced pussy and surrendered another cumload.

Then I pulled back and watched in fascination as Maggie squeezed her cunt muscles until my watery cum drizzled from her hole onto Barbara's open mouth and outstretched tongue.

I've been on this earth now for 48 years, and that is still the highlight of my sexual experience.

We were true to our word. We dropped off a thoroughly-sated Barbara off at her apartment in Austin before heading up I-35 to Oklahoma City.

Maggie and I seemed to break through a barrier of sorts after that night, because the rest of the tour was like that. It was night after night of orgies, as we followed the Dead from Oklahoma to Kansas City, St. Louis, St. Paul, Alpine Valley and finally Denver.

As memorable as some of those nights were, I think that was when the bloom fell off the rose. I saw that Maggie was really just a sex-hungry slut, and that feeling was reinforced when we got back to the Bay Area.

We made one final tour together in August, a couple of nights in Oregon, at Portland and Eugene.

But, by then, I'd begun to sour on her Tourhead friends, seeing them for the vagabonds they really were. There were a couple who were all right, but most of them were leeches, drifting through life without any purpose other than the next buzz, the next show, the next handout.

More to the point, I'd begun to suspect that Maggie was supporting herself by means other than working at a record store. She would go out some nights without really being specific about where she was headed or who she was going out with.

I followed her one night, just out of curiosity, and she met this biker who carted her off to some unknown destination. But it really didn't matter, because I knew she'd come back with either a roll of 20s or a bag of weed or some cocaine. And I knew how she'd gotten it.

The morning I finally reached the epiphany about how old she looked was the day we were supposed to start packing up for the next tour, to Pennsylvania, New York and possibly to Europe.

I wanted no part of it.

^ ^ ^ ^

"Maggie, I'm not going back east with you guys," I said. "It's time I got my ass back in school and got on with my life. These past few months have been fun, but it's over. I just can't do this indefinitely. I've got more to offer life than just aimless wandering following a rock-and-roll band. I mean, they're great, but they're not the end-all and be-all to life. It's time for me to grow up, and I'm not going to grow up if I stay with you."

"So that's it, then," she said evenly. "You're just going to walk out of my life, just like that."

"Mags, you and I both know we don't really love each other," I said. "If you loved me you wouldn't be hopping on some fucker's bike and going off to turn a few tricks a couple of nights a week like you have been. If I loved you, I'd have never come on to that chick in Texas like I did. We've been using each other, and it was fun while it lasted, but I'm getting burned out and I need a dose of reality."

And that was it. We parted as friends, sort of, and while she packed up the Microbus to head to Pennsylvania, I gathered up my meager possessions and moved back in with my parents while I cleaned up my act and sorted out my future.

I decided I needed a fresh start some place away from San Francisco. I'd lived in the area all my life, and it was a little too familiar, and there was a little too much temptation. I didn't need the siren call of drugs or the nearby allure of Maggie May luring me away from the business of life.

If I was going to get serious about college, I needed some place without the distractions the city offered. I didn't want to get too far away, though, and the place that presented itself, believe it or not, was Fresno.

I know, Fresno is often the brunt of hick jokes from folks in LA and San Francisco. It's stuck off in the middle of the Valley, it's kind of a rural area and it's not exactly a cultural hotspot.

Which meant it was perfect for my purposes. I enrolled at Fresno State that winter and breezed to a degree in business.

My nine months as a professional Deadhead hadn't been entirely a waste. I learned some interesting survival skills, like how to live on a tight budget and how to hustle for a buck.

I got in with a band that was playing some interesting alternative-style rock (yes, in Fresno), and I was able to make enough to live on while I was there.

And, as a bonus, I met a really nice woman who was studying to be an occupational therapist and we ended up getting married not long after I graduated from college.

We settled in Oregon where I went to work for a well-known company and we have three kids and two dogs.

I know it sounds like a sellout from my Deadhead values, but it's not really. Hell, the Grateful Dead themselves became a multi-billion dollar corporate empire, and I didn't hear a lot of fuss about them selling out.

As for Maggie May, we stayed in touch for awhile, then she just sort of faded away. Every once in awhile I'd see her at a Dead show and sometimes we'd talk, and I always -- always -- saw a vague look of regret on her face, like she maybe wished she'd done more to keep me.

jack_straw
jack_straw
3,234 Followers