I’ve had countless first dates in my life. Some have been amazing, others God fucking awful. I’ve had incredible one night stands and swore they were the beginning of a steamy love affair, only to call and call but never hear from the girl again. I’ve unexpectedly met women’s parents on first dates, been farted on, had my keys thrown into the street, been called a faggot, had my asshole eaten out, puked on a girls shoes after eating a rancid oyster and had my favorite mustard sweater stolen. I still miss that fucking sweater.

So it surprises me that even after all that… I still come across scenarios that my first date playbook doesn’t have a counter move for. Enter Mandy: A thirty-year old publicist I met at a friends birthday party a few weeks back. 5’10, shoulder length brown hair, slightly broadened shoulders and one hell of a body. Her face totally reminded me of Lady Gaga.

Mandy was the only single girl at the party so I said fuck it and introduced myself. She spoke softly and the music was so fucking loud I literally couldn’t hear half of what she said… but of course constantly smiled, nodded and agreed as if I’d heard every single word.

There weren’t any sparks at all between Mandy and I the night we met. Through our twenty-minute conversation I struggled pretty damn hard to keep the conversation flowing. I’d ask her a question about herself, she’d politely answer, I’d quickly scramble to come up with another, and repeat. God I hate that.

She didn’t probe or try to find out anything about me and smiled at a few of my jokes, but generally seemed disinterested. It almost seemed as if she too couldn’t hear me and was playing along just as much as I was… either that or she just genuinely thought I was stupid. Because I felt stupid.

I took the pussy route by not getting her number that night and friend requested her the next day instead. Then, in a moment of boredom or maybe even slight desperation, wrote her a private message telling her how nice it was to meet her.

That’s when it got confusing.

Her response baffled me: Oh, hey! So glad you wrote Was wondering if I’d ever bump into you again. I had fun too! A little lou,d but fun. Hope to see you again?

Confused, I responded: Next Friday?

Sure!

I met Mandy at a rooftop bar in West Hollywood not expecting much. Curiosity about her enthusiasm in seeing me again had me more than anything else. She walked out of the elevator wearing a short white skirt, some dominatrix looking black shoes and a tight black top. Sexy as FUCK. She gave me light hug and was sure to not get too close.

I need to pause the action for a sec…

Look… I do OKAY financially. I can afford a decent apartment, a super low-end luxury car, I pay my bills on time and don’t really worry about my portion of the check when at a birthday dinner with friends. However, money is still a constant worry. I don’t save (who the hell does?) The unexpected $300 bill for lab tests after a check up (and that’s with medical insurance) or annual car registration send me spiraling into a pit of anxiousness where I freak out about my financial future, if I’m living above my means, if I should try to save more and complain about how food is now SO fucking expensive.

I don’t ever mind reaching into my back pocket and taking care of the check when taking a girl out. In fact, I enjoy being “the man”. I also always try to take my dates to decent bars or restaurants. I’m not twenty-five anymore. Pabst Blue Ribbon’s at dirty bars don’t cut it. And I assume it doesn’t cut it for most of the women I meet.

But I always wonder where being a gentleman crosses over into stupidity and being plain irresponsible. This train of thought started with our first two drinks, to the tune of $16.00 each, which of course had more yummy tasting stuff in them than liquor and almost immediately required a second round.

Forty minutes into the date and I was in no better of a position with Mandy than the night we met. I’m no genius, but I have enough insight to know when there isn’t any vibe. And by no vibe I’m talking about a date that consisted of me asking her a question, getting an answer, then sipping my drink or looking elsewhere for five to ten seconds while I tried to think of another.

It felt like a job interview for pussy. A job I definitely wasn’t getting.

I rarely find myself in such a shoulder shrug of a situation. My dates generally fall into one of three categories. 1.) Pretty good. 2.) Fucking amazing. Or 3.) Get me the FUCK out of here! Mandy and I weren’t having a bad time up there on that rooftop… but it definitely wasn’t a good time. The date almost felt like dinner with a client.

We ordered a third round and our waitress asked us if we wanted food. “I’ll look at the menu,” Mandy said. I wasn’t hungry but didn’t want to be rude and agreed to share two appetizers. Through my peppering of questions I learned that Mandy has been skydiving thirty-one times, bungee jumping twelve times, lived in a South American jungle for a month, climbed mountains in Peru, ate insects in China and is a lover of all things extreme.

The sense of adventure didn’t match her barely audible voice or lack of words. I only hoped there was a freak buried behind those Lady Gaga features. I seriously wondered if a girl like Mandy could be good for me and help me break out of my always-fearful, constantly neurotic Jewish shell. Or if she’s just a fucking loon.

As midnight approached we decided to leave. The check came. $149.27 not including the $20% tip. I paid it while wondering if I was a total moron for spending almost $180 dollars on a first date. Or if thinking that way made me a cheap bastard, or a plain bastard, or ungentlemanly. I wondered what else I could’ve done with her or what other guys do on first dates, and if I was doing way too much.

I walked Mandy downstairs, we gave each other a terribly light hug and she walked away uneventfully. I left and walked back into my apartment door… flat. Emotionless. Bland. All up until I got another facebook message from her at 12:46am: Hey! Thanks so much for taking me out! Had a great time. I hope we get to hang out soon

Maybe.

But I’m NOT jumping out of a fucking plane.

1.) WHAT am I DOING? 

2.) My stomach is kiiiiiiillllling me.

3.) Please Lord and Greg Giraldo don’t let the waxer be remotely attractive or one day under forty-five! 

4.) Will pooping be incredible from this point on? 

5.) Is she going to wax INSIDE? Like… IN the crack and ON the butt hole? 

6.) Am I fucking gay? 

7.) Will my pants fit after? 

Since the age of twenty or so… ass-hair has always been a major insecurity for me. And  it’s not like I’m all that hairy of a guy. My chest and stomach are lightly wooly, as are my arms and legs like every other man on earth. But for some fucking reason at the age of twenty or so my ass went full-moon-wolf-man on me.

Beyonce’s weave… it was ON my ass. I bought a hair pick and relaxer for it. I could’ve shaved it and donated the hair to cancer patients. And the hair just got longer, thicker and more wiry as it traveled into my black hole of an ass crack. The aftermath of each morning crap was chaotic mess of toilet paper, baby wipes and multiple flushes.

And it’s pretty much destroyed every sexual experience I’ve ever had and caused me to spiral into into a silent series of self-deprecating thoughts as soon as a woman’s hand brushed my bare ass or lower back. Omg, she thinks I’m such a fat gorilla loser. I’m so gross. There’s no way this hair doesn’t stink. Ugh. I disgust myself. 

Getting my ass waxed was something I’d sort-of fantasized about for years with the same excitement one might get when thinking about getting liposuction on those parts excersise will NEVER EVER FIX. But again, self-deprecating thoughts: It’s gonna hurt like crazy. It’s gay and uncomfortable. Who would I even call to wax me? I DON’T want anyone looking at my ass in the daylight. 

But then, a few months ago, I went to an old friends house for dinner. His girlfriend cooked. This couple is heavy in the swing scene and frequents sex parties and Burning Man type events where they both comfortably walk around naked, something I’ve never been too keen on. “We love walking around nude,” his girlfriend said while pouring me more wine. “Two days before any event we both go get waxed and tanned!”

I pointed to my friend, “YOU get waxed?!”

“Yup! For the past ten years, sack & crack once a month! It’s so much cleaner than shaving. It doesn’t hurt nearly as bad as you think and women love it.” His girl nodded in agreement.

My knee jerk reaction was of course — Man… Fuck THAT! But as the weeks went by, and I began to think about how much the waxing of my tuchas would scratch away my ever-present insecure itch, I decided to go for it and asked my friend for his waxers number.

“Her name is Olga, tell her I sent you. She’s fantastic.”

I called and made a 2pm appointment on a Saturday afternoon… while nauseous. Olga, who had a thick Russian accent was very polite and gave me the address to her Venice Beach apartment. “I’ve never done this before and I’m a little nervous,” I pleaded. She laughed. “Don’t vorry! You’ll be fine!”

I parked at 1:50pm with an elevated heart rate, and elephant on my chest and my boxers briefs dampened by my sweaty thighs and taint. I knocked on apartment 2b. As soon as she opened the door twenty percent of my angst dissolved. Olga stood 5’2, looked to be in her early fifties and a solid fifty pounds of extra poundage stretched out her tight, white medical scrubs. Thank. Fucking. GOD! (And Greg Giraldo!)

She led me into a tiny, converted, prison cell sized waxing room that looked like something out of an Eastern European psycho ward, complete with a towel covered table, scuffed up white linoleum floor, peach colored walls, a small stool, gauze, creams and a large medical light coming from the ceiling.

“Take off pants and gyet on table,” she instructed with her thick Russian accent. I did and and climbed onto my stomach, but left my boxer briefs on out of sheer embarrassment.

“Do you vant same thing as your friend? Backside and bulls?”

I jolted to on my side, “NO! ONLY backside!”

“Okey… Do you shoot da steroids?”

“Come again?”

“If you shoot da steroids… you bleed a lot.”

JESUS! What the FUCK am I doing here???!!!! 

“No, I don’t use steroids.”

“Okey… Only backside?”

“YES!”

She pulled my briefs down to the top of my thighs, flipped on the medical light and started examining my jungle-like ass hair through a massive magnifying glass. I glanced back and saw her twisting some wax around a wooden tongue depressor. Fuck. FUCK! It’s going to KILL. I need to GO! 

She smeared a warm stick of wax across my bottom like she was icing a cake. I could feel my disgusting butt hair pulling against it. She smacked a removal strip down and began pressing. My heart rate shot up another ten bpm and spear like pains stabbed my chest. Shit! SHIT DUDE! 

RIP!

Hey, that wasn’t so bad! 

She began patting my bum like a baby to minimize the light sting. I liked it and wanted a baba. For the next ten minutes she continued waxing the grotesque, monkey like hair off my fanny. I felt a decade of emotions and stress float away with each stingy tear.

I FUCKING LOVED IT!

“Okey… please grab cheeks and spread so I can do crack.”

Oh… FUUUUUUCK!

I’d never wanted and dreaded anything so much at the same time in my entire life. I felt certain she’d either puke after digging around in that pale, flabby cave of a crack of mine… or rip my asshole completely inside out.

I reached back with both hands and pulled em apart. She moved the light down closer and put her face within stink distance, examining thoroughly. She lathered the top of my crack with wax. It tickled and I squirmed. She pressed in the removal strip. I took a deep breath and closed my eyes!

RIP!

IT HURT SO FUCKING GOOD! She gripped my lower right cheek and pulled hard, smearing more hot wax in the LOWER portion of my ass. My toes curled uncontrollably and my starfish puckered like I’d just fed it a lemon slice. The strip went on. Her finger tips pushed hard into my crack. This was IT! The most hairy, dark, messy part of my backside.

RIP! 

An involuntary groan flew out of my mouth, “Ughhhhhhh!”

“Are you okey?”

“YES! GOD YES!”

Olga spent a few more minutes clearing out the weeds before wiping down my brand new, bowling ball like badonkadonk with some sort of refreshing liquid. She handed me my pants. “Ve’re done!” I slid my boxers back up and put my jeans on. For the first time in my life I could actually feel them!

Hurray!

Olga charged me forty dollars. I gave her sixty and a bear hug. I now see Olga every six weeks… And yes, pooping is incredible. Sex is confident and actually enjoyable. And no, it’s not gay.

So if you’re a man with a shameful bushy bum bum, take it from another, super insecure, formerly fearful and still fucked up guy…

Wax that shit.

Sigh. 

Samantha, a twenty-nine year old struggling comedy writer a friend hooked me up with had amazing facebook pictures. The shot of her hoisting up a tall brewski showed off her beautiful half-Latin smile, white teeth and brown eyes. And the other one where she wore skin-tight gold pants and a teeny top at some sort of Mardi Gras type festival proved our mutual friend wasn’t lying about her 5’7 frame and five day a week yoga regimen. Ugh. Her body looked SO fucking good I almost licked my laptop screen.

Baby-got-a-bangin-hip-hop-music-video-body aside, what I really liked about Samantha was her easy-going and always chuckling attitude. A funny girl has always been a plus, and as I’ve gotten older that plus has turned into a must. “Let ME tell you a funny story,” I said while trying to come off equally as entertaining during our first phone conversation, then stammered into a four minute long ramble about how I freaked the fuck out the last time I smoked weed.

I finished…

Brief silence…

“But I thought the story was going to be funny?”

She was also humble when explaining her dire financial situation. “I work all day, seven days a week and make zero money. I don’t know how I keep managing to pay my studio apartment rent each month. Half the reason I’m going out with you is for the free food!”

With that, I safely set up a dinner date instead of the always-easy-to-get-out-of “drinks”. I’ve struggled financially plenty in the past and totally got it. And it’s not like I make all that much bread, but treating a funny hottie and potential eff-buddy or wifey to a swanky LA restaurant is always in my budget.

When I woke up on the day of our date I still didn’t know where to take her, but the morning started off with some very positive news at work that put me in a celebratory mood. I said fuck it and made a spur-of-the-moment reservation at Geisha House. And for those of you who live in LA…

Yes.

Geisha House.

For the out-of-towners… Geisha House is a super pretentious, overpriced, Kim Kardashian, Paris Hilton, need to be seen, every-episode-of-Entourage-was-filmed-there hellhole. You can smell the collagen, fried hair and desperation when you walk in. It’s impossible not to see one of The Hills cast members sipping a rainbow colored drink. Loud conversations about production deals, development contracts and screenplays fill the air like a philharmonic being played by blind monkeys.

It was a DUMB move and NOT normally my style, but the restaurant was three blocks from her house and the first place that popped into my head. I thought — Fuck it, I can be Hollywood for a night. And Samantha seemed like she would’ve been happy with a burrito truck, so I went for it.

The date had actually gone quite well… all up until I realized what a stupid fucking irresponsible dickhead I am. Much better than I’d thought, considering it was a partial blind date and Samantha looked even better than her pictures, which NEVER EVER HAPPENS!!! Her thin, white summer dress showed off her toned arms, tight legs, b-cups and made me bite my fist when quickly peeking at her utkatasana’d rump-shaker.

I went fucking crazy when ordering dinner. Thirty-five dollar dry aged kobe rib eye steak? Bring it. Rare toro sashimi at a crazy overblown market price? Yes, I’ll take TWO of them shits. Oh, and a bottle of the most expensive sake you have please. Samantha…  Anything you want, girl. I’m feeling good; you’re fucking hot and super poor and I’m DOWN to throw around some cash.

Through dinner laughs were plentiful, accidental knee-rubs under the table weren’t uncomfortable, sarcasm was heavy and it looked like Samantha and I would definitely be more than just one date. She was quicker than I was and continually made me laugh. I loved it!

We were halfway through shared desserts, rice flower banana fritters and hot brownies topped with fresh cream and berries. I felt SO fat. Didn’t matter. Because as we all know a woman sharing a dessert with a man on a first date is code for: Yes, I WILL let you sloppily stick your tongue down my throat after you hug me goodbye. 

I should have been stoked.

But then… I realized it.

Oh… FUUUUUUUUUUUCK!

The awareness punched me in the face and killed all of that days excited energy and my hope of a funny fuck. I began to sweat profusely and screamed at myself — You fucking fat pig IDIOT! What am I going to say to her?! How am I going to say it?! What the FUCK do I next?!

As we finished dessert I got up and went to the bathroom in a pathetic effort to buy time. I grabbed my phone in a panic, scrambling to think if I knew anyone who lived close by to come rescue me. I didn’t. I was FUCKED. I knew that by the next morning I’d be the laughing stock of her friends, family, the bloggosphere, TMZ, CNN and whoever else caught wind of my blunder.

As I sat back down my heart was pounding like a techno track. Our struggling actor/model waiter put the check on my side of the table. PRICK — I thought as I stared at him like he’d just screwed my sister… and forced her to do anal.

I flipped over the bill – $269.72

My life is fucking OVER! 

I looked up at Samantha with a worried smirk.

“Samantha, you’re not going to believe this… but I forgot my fucking wallet.”

She chuckled.

I laughed back, “I’m totally serious.”

“NO!”

“Yes.”

“How much?”

“269.72. Not including tip.”

“Umm, I think I have $200.00 in my account.”

“We’re fucked… and I just blew it.”

Silence.

Shame. Embarrassment. Loserville. Fucking asshole.

I called the waiter over and shamefully explained the situation. He laughed. I told him I wasn’t joking and almost punched him. He left and returned with TWO managers AND a security guard. Paris Hilton’s friends began to look in our direction while trying to figure out who I was and why restaurant staff surrounded our table while I practically cried.

They took all my information and made me promise to call when I got in and give them my credit card number over the phone. I apologized profusely; thankful they weren’t breaking my legs and looked like a MASSIVE pussy doing so. Through the whole thing Samantha stared at me in silence with a look of utter shame. She wasn’t impressed with the way I was handling the situation. She looked at me like a bitch. I was a bitch.

I got my car from the valet. SHE had to pay for $7.00 plus tip. Heavy silence during the three-block drive to her house. Pathetic apologies as I pulled over. “It’s okay. It happens!” She said, trying to make me feel better. No hug. No sucking face. No “let’s do it again next week.”

When I got home I called and paid the tab. I haven’t heard from Samantha since. I’m not calling her. I need to jerk off to make myself feel better.

Each time I see a viral piece of tranny bait the same thought always goes through my head: Who’s watching this shit? 

Survey says!

#1 Answer: Straight men.

Let’s get into this shit, shall we?

Men are infatuated with their genitalia. We’re constantly feeling, tugging, massaging, pulling, jerking and abusing our cocks and balls, gritting our teeth and trying to shoot our huge cum loads on to anything we can, as hard and as often as we possibly can.

That has nothing to do with this post; I just needed to say that.

All jokes aside… us guys are all secretly interested in other guys schlongs. We keep our peripheral vision WIDE open in bathrooms and sneak peeks at the peckers next to us. Trust me on that. I’ve caught guys looking dead center at my dick… mostly in airports. But go take a piss at any major sporting event and quickly glance to your right or left and tell me I’m wrong.

Anyway… When we watch porn we examine the length, width, head and ball size of the gigantic wieners attached to the male porn stars. And we don’t do these things because we’re gay. No no… In addition to seeing how our own skin flutes compare with others, it’s simply because we’re totally infatuated with sex and have a slight attraction to the penis. I started jerking off to tranny porn in my early twenties, and eventually took it to a whole other level. I break it down in much greater detail in my book. And I didn’t do these things because I felt like I was gay. Like… not even close.

So then why?

A couple of childhood sexual experiences left me with an eyebrow raised when thinking about a penis in a sexual situation. Through my teens and early twenties I always wondered what it might be like to feel another one, pull one really hard, slap one, suck one with my girlfriend or God forbid… make one cum. (I’m nose diving into hell for this post)

But I wasn’t gay. I mean… I really, really wasn’t gay. And wasn’t fooling myself into thinking I wasn’t gay either. I LOVED women. I pursued women. I romanced and chased women. Men, in-fact turned me off. Through the years some of my girlfriends had gay best friends who would hit on me. Men gave me eyes and one-liners about how I “was cute” in restaurants or stores.

But no interest.

NONE what so ever.

The thought of being with a hairy, smelly, stinky, farty guy made me fucking sick. But there was something about the ding dong that kept me interested and turned on. Kind of in the same way I live a vegetarian lifestyle but can definitely appreciate, and tear up a fifty dollar steak once in a while.

Ok… horrible analogy but you get where I was going with that one.

So for me… tranny porn was the perfect middle ground.

Now there are a lot of transexuals that straight up look like men. They’re large, thick, stubbly, have weirdo cheekbones, unrealistic asses and bad makeup. But there are also a chosen few that look exactly like women. They’re thin, hairless, shaped like a female and surgery free. And when I started watching videos with these types of transexuals it seemed to scratch an itch I hadn’t been able to reach for years. The best of both worlds if you will. A smokin hot chick-ish… with a custard launcher.

There are A LOT of men who watch tranny porn. And I can almost guarantee your friend, homie, brother, co-worker, workout partner, wrestling buddy, fuck friend or boyfriend is one of them.

But they’ll NEVER tell you about it. People are reluctant enough to talk about their “normal” sexual turn-ons or favorite types of porn as is. So when it comes to fetishes… forget about it. Like me, they’re afraid of being judged and looked at like freaks. They’re afraid of society, the world and even YOU making fun of them.

I’ve opened up to a few of my better female friends about my taste for tranny porn. Each responded by telling me either their current lover, or ex, also loved transsexuals.

The same conversation applies to gay porn. Straight men love it. But again… you’d never hear a straight guy say it. A few months ago I was skimming through a porn site called X-Tube, which allows people to upload their own porn, and came across the profile of a guy who’d posted probably forty videos of himself sucking other guys cocks through a glory-hole… but he’d categorized himself as: Straight

I sent him a private message questioning if he really was straight. His response came no more than five minutes later: I live a completely straight lifestyle. I have no interest in dating men or anal sex. I just enjoy oral with guys from time to time.

And yes… a man posting his self-made glory hole videos of himself swallowing loads may be extreme. But the point is… there are many more men out there that feel this way than you’d think. Some of you women reading this have dated them, fucked them, and may be involved with one or two of them now. Some of you men reading this had beers with that dude last night. Some of you reading this are that guy.

So why am I writing about this shit? Because I don’t want men (and women) with the same feelings to feel alone. I know they read my blog because I’ve received emails from them. It took me years to accept and figure out the way I felt. And in the end there’s nothing wrong with it. With YOU. We’re all a little bit crazy, a tad fucked up and really perverted. But for some reason our unrealistic, puritanical socially makes us believe that we’re bad, or gay, or sick, or twisted for doing what makes us happy or gives us pleasure.

It’s so ridiculous.

Own whatever turns you on and makes you happy. If you’re a straight guy and want to diddle a ding-dong, do it. If you’re a straight woman and want to cuddle a clitoris, make it happen. If you’re a tranny and want to jerk off to horse porn, then by golly… jerk until the cows come home. Does that mean you need to spread your business to the world? No. But you also don’t need to feel ashamed.

Full disclosure: The author had some of these experiences on his blog some time ago, which is how I found out about this book. If you’re a fan of the blog and are wondering if this is just a repackaging, it isn’t. Some of the stories will be familiar, but all of it is much more fleshed out, with deep thoughts about himself and how it made him feel. In his blog, he explored his questions of sexuality and how dates would make him feel, but not nearly to the extent he does here.

As the other reviewers have said, it’s rare to find a male writer so honest about his sex life. From half-page decipherings of a casual text to long discussions about when he feels a breakup is about to happen, this guy doesn’t pull any punches. He’s a bit more serious and introspective than he was in his blog, but some of his stories are still hilarious.

If any girls are wondering if they’re just gonna hear a bunch of ridiculous stories – This isn’t some Tucker Max wannabe trying to out-Bro himself. It’s an honest look at dating in LA, an honest look at the thoughts of being a guy.

My ex and I had great communication. I feel like my relationship with her was the first real adult relationship of my life, and the only one I still consider as a true success (even though she took a job on the other side of the world and left me. I hate her face, soul and existence.) The unfiltered openness we had between each other started with a conversation about monogamy one night while on our way back from a bar. She was pretty drunk and said, “I don’t know if I can realistically be with one person for the rest of my life… sexually.”

Anger. Insecurity. Judgement.

“What does that mean?” I responded in almost a bitchy tone, as it was still early on in our relationship.

“I just mean… that… I hope my husband and I can have a series of conversations and figure out a way to open up our bed and keep our sex life fresh and fun.”

My mind completely distorted what she’d told me. I heard, “You’re not good enough for me and I need to cheat and fuck other guys with huge dicks that have BIG money and swallow their loads. I want ten cocks in my ass while being showered by a fucking jizz sprinkler!!!!”

In my twenties I probably would have held on to that altered version of what she’d said and allowed it to fester inside of me day and night causing a cloud of paranoid jealousy hovering over my head twenty-four hours a day. I would’ve then silently questioned her whereabouts or wonder if she wanted to fuck the hot actor waiter at Sushi Roku, her rich boss or the sandwich-making hipster at Whole Foods. Visions of all three of them covering my girlfriends face with the jizz sprinkler would’ve run through my head… in slow motion… with awesome rock music… and Scorsese quality cinematography.

I need help.

Anyway… during that car ride I decided not to respond and hold on to what she’d told me… relax… take a breath… and think about it. I wanted to hear more from her and nervously brought it up shortly thereafter when we were both sober. And when I did, I tried with all my might to listen without any filters.

“I just don’t know if monogamy is reality,” my ex said calmly. “I don’t mean that I’d like to see other men alone, or that I’d like you to go on a date with another girl without me. But… I wonder what would happen if we brought another girl into the bed? Or even a guy? Or even a couple? I don’t know if I can have strange man’s penis in me without getting to know him first… and I don’t know if I want to see you fuck another girl. But maybe I can? Maybe it will be fun for the both if us?”

The conversation scared the shit out of me. And as weird as it sounds, it scared me because of how mature it was. I couldn’t believe we were even entertaining the idea. If I’d even made jokes about being with another chick with any of my past girlfriends I risked waking up in the E.R. with half a dick and a hazy memory.

But there we were… sitting on the couch just laying it all out there. Our fears. Our desires. Our fantasies. And it was actually okay! There wasn’t any anger, guilt or weirdness. The strangest thing about it though… is all it took was total honesty and fearlessness. A concept that had seemed so foreign up until that moment.

I had secretly always wanted to have that conversation with a girlfriend. But was way too afraid to break societies definition of the word faithful: NO looking, NO touching and NO flirting. Sex with one person and one person ONLY. No ifs, ands, or buts. And those who break those rules, or even slightly crack them are the SCUM of the earth! Weird. Bad. Not to be trusted. Fucked up and uncool.

I also didn’t think I could ever have enough confidence in myself, or in my relationship to get past the point of not being jealous or insecure.

I’ve always been very open sexually and willing to try almost everything. I really only had four big “No’s” on my list. 1.) Pain. 2.) Animals. 3.) Blood. 4) Poop or pee. I knew I’d be more than okay with bringing another girl in the bed. What man wouldn’t? I’d had three ways in the past but they were on some drunken college debauchery shit without any emotional attachment. I’d never had one with a serious girlfriend… but I didn’t think it would matter.

However, I wasn’t sure if I could actually see my girlfriend fuck another dude. But maybe I could? And as we discussed it more and more the fear dissipated, the walls broke down and I started to feel like as long as we continued to be completely honest and respect each others feelings, that I could be comfortable enough to go ahead with some initial experimenting.

After several conversations we decided to start the exploration with two things. 1.) Bring in another girl… And 2.) Have sex with each other in the same bed as another couple. Watch, be watched and have some other bodies in the mix.

In the same way I was reluctant to see her fuck another guy, having a three way with another woman was just as scary for her. She liked women and had slept with many in the past. She’d also been “the girl” with a couple or two while single. But like me, she was scared to go that far with the man she cared about. Afraid that I’d fall for the other girl or become more turned on by her.

Through the process of trying to find that special woman I had to be completely aware of my ex-girlfriends feelings. It was my duty to make sure she felt loved, sexy and that she was she only girl I cared for, which was of course the truth. Finding that third piece took months and came through a female friend, who had a mutual friend interesting in exploring with a couple. We all hung out in groups a few times at bars and parties. Then had a couple of two on one dates before the three of us finally ended up back at our place one night.

The first three-way I had with my ex was one of the hottest sexual experiences I’ve EVER had. It’s one thing to have a three-way with a couple of chicks you don’t know, but another to have one with someone you’re totally in love with, totally comfortable with have a vested interest in making sure she’s pleasured.

In the moment… any fears or walls either of us had completely vanished. So much so that in the midst of it all my ex turned toward the other girl and said, “Do you want him to fuck you? I think he needs to fuck you!”

Whatever you want, honey!

Oh, I fucked her alright… while my girlfriend licked my asshole, and the experience took our relationship to a place of intimacy and trust that I’d never had with a girlfriend before. Like not even close. The next day my ex and I were so tuned up from the night before, and so much closer to each other we fucked four times. We continued to have bi-monthly dates with the same girl, and eventually a few others, and quickly jumped into phase two: Sex in the same bed as a couple.

And that’s when things really became interesting.

To be continued….