Ask Meredith!

I’m bringing this back for 2018! This week I’ll only be answering one of your reader emails, but in the future I’ll pick my 5 best questions of the week and answer them here. Your identity is kept anonymous and I hope my advice helps you guys out!

 

Q:  I love the hell out of my wife, and we have amazing sex…but I have 3 things where I’d like some improvement.

1- How do I convince her to swallow?  
She’s amazing at BJ’s, but she won’t even let me cum in her mouth.  She’s done it once or twice when I don’t let on that I’m close to orgasm, but she says the texture is disgusting to her.  She says the texture on her tongue is nasty.  She’s warned me to always tell her when I’m close, that she doesn’t like the surprise.  Truthfully, I don’t care if she swallows.  I just want to cum inside her mouth.
2- How do I convince her to start some ass play?  
She likes pressure against her asshole when we are fucking.  I just need to know how to get her started in letting me get a digit or the tip of my dick in her ass (by the way I’m just average sized).  What’s the best way to gradually, smoothly break her into this?
3- How do I convince her to wear lingerie?
I know she is self-conscious about her body, but I tell her all the time how much I love her body and when she dresses slutty.  She also says she doesn’t like to make a “big production” out of sex.  I love the fun and anticipation though.  I’ve bought her items in the past that she thought were too small on her…which made her upset.  Any ideas on how to approach this?
A: It’s normal to want to explore new things in your sex life when in a long-term relationship or marriage. And it’s really easy to fall into a routine when it comes to sex as you become more and more comfortable with your partner.
1- Personally, I don’t really get the texture issue (and I’m VERY particular about textures when it comes to food) because semen is really no different of a texture than a milkshake or thin smoothie. I CAN understand the taste being an issue, because sometimes it just does NOT taste good. This one will probably be tricky, and at the end of the day if it’s just something she is not comfortable doing, then that’s just how it’s going to be. Tell her that you love the way she gives you head and how great it feels and how it would mean a lot to you if sometimes you could finish the full experience in her mouth. Have a drink ready for her to chase it with quickly so the semen doesn’t spend much time in her mouth. If she is just completely averse to it, then leave it at that and don’t push her, maybe revisit on your birthday. Be understanding and okay with it if she says no.
2- Often times women (and men) are wary of ass play simply because it still seems a little taboo to them. If she enjoys the pressure during sex, get some good lube (Gun Oil brand is the best for anal/ass play) and start very slowly with just the tip of your pinky. Go slow. Starting with baby steps is the best way to build up to doing full on anal. Play the long game on this one, don’t try to do too much too fast, and focus on her pleasure. Knowing she is enjoying herself will make it better for you too.
3- I can totally relate to the way your wife feels about her body and lingerie. I am not a lingerie girl, I literally own like one matching set and I never wear panties so I always feel really self-conscious and weird wearing lingerie. This is another one of those conversations where you have to compliment her and let her know how sexy you find her and how much it would mean to you for her to dress up every once in a while. Men—I can not stress this enough—unless you know your partner’s EXACT sizes, don’t buy the lingerie for her, let her pick it out. It’s happened to me a few times too where a man thinks he’s doing something fun by picking out lingerie for me to wear and then I go to put it on and it’s like 2 sizes too small. Which, bless your heart for thinking I’m a size medium in panties, but it can be really humiliating and make a woman feel awful about her body. Pick it out with her. Or let her know some things that you like, hand her some cash and tell her to go pick something out to surprise you with. That way she has control and gets to choose something that she likes on her body, and it’s a total surprise for you. If she feels good and confident in it, that’ll make it even more fun for both of you.
Send me more questions y’all! About sex, dating, life, literally anything that you think I could give you some good insight on. I love talking to you guys and I really enjoy being at least somewhat helpful. Fill out my contact submission form or email me at meredith@meredithactually.com.
Have a great weekend y’all!!
Xoxo,
Meredith

The Lifeguard Stand

Tinder might not be good for a whole hell of a lot of things aside from a random hook up and a chlamydia scare, but occasionally you find a cool guy that makes you remember what dates are supposed to be like: FUN. Kyle was one of those guys. He’d super-liked me, which was flattering, and surprising since I usually only get super-liked by guys I wouldn’t go out with in a million years. Kyle was cute, dark hair, nice smile, and his profile mentioned space, art, and the fact that he wasn’t looking for a relationship so obviously I had to swipe right. His first message to me was nothing short of perfect:

“Hey Meredith, I’ll eat Totino’s and talk aliens all night with you. Just please let me take a picture in your Guy Fieri bathing suit.”

I couldn’t stop laughing. I’d made one of my Tinder profile photos a picture of me wearing a ridiculous one-piece swimsuit with Guy Fieri’s face on it and mentioned loving aliens and pizza rolls in my bio. I always appreciate when a guy pays attention to the goofy things I do and say and not just the way I look. I might not have been looking for a soul mate, but I’m a lot more likely to want to fuck a guy I can hang out and have fun with, and Kyle seemed like he was going to be a blast.

Kyle and I messaged back and forth only briefly before making plans to meet. He suggested oysters (how do all these boys know about me and oysters?) and asked if I knew of a place near me where we could go and that he didn’t mind coming to me since he lived close to downtown, which was at least a 45 minute drive from me in Playa del Rey where I was living for the summer. I suggested Playa Provisions, and he quickly gave me his phone number and said he’d see me there at 8. It’s always a fun feeling to actually be excited for a date. I like when a guy makes a plan and doesn’t waste time going back and forth deciding on a place and time. Our plans were made and set in stone within like four text messages. I was already a fan of Kyle at this point, so I threw on a cute black t-shirt dress and sandals and got ready for our date.

I got to Playa Provisions first and was seated in a corner. I ordered a drink while I waited, and just as the server brought it to me in walked Kyle. I loved his sense of style immediately. Great smile, and a trendy haircut, some fitted jeans and a vintage looking letterman jacket with the sleeves pushed up over a black t-shirt. I noticed the rose tattoo on his hand right away and was instantly like twenty times more attracted to him. “Meredith?” he said as he walked up to the table. I stood and greeted him with a hug, and we sat down and got down to business ordering oysters and rose’ and the conversation flowed as easily as if we’d known each other for years. Oysters and rose’. I swear, it’s like these guys are reading a manual on how to get in my pants.

After dinner we decided to grab another drink at the classic Playa del Rey dive, Prince O’ Whales. If you have ever spent any amount of time in Playa, you have definitely been to POW and you have definitely blacked out there. It’s the quintessential dive bar full of locals and Loyala Marymount kids drinking cheap beers and playing songs on the jukebox. I love that place, and it was the perfect next stop for Kyle and I.  We had a couple of beers and naturally I played Toto’s “Africa” on the jukebox (because duh, it’s my favorite song), and then Kyle went in for the kiss. He was an amazing kisser. We laughed and made out and were generally obnoxious at the bar for a little longer until Kyle suggested closing out and going out to the beach. It sounded like a good idea to me, so away we went down to the totally empty beach around 1am.

We took our shoes off and walked along the beach close to the water, then Kyle stopped, took his jacket off, and laid it on the sand for us to sit on. We started making out, and before I knew it our hands were all over each other. He was intoxicating. He had one hand in my hair as he kissed me while his other made its way up my inner thigh. I never wear panties, and I could see the surprise in his eyes when he realized I had nothing on under my dress.  He smiled and said “no panties huh? Bad girl…” as he started to play with my clit. This was beyond hot. A dark empty beach, the waves crashing in front of us and having the hottest make out session I’ve had in a while, I wanted more. He started working his way down my body and before I knew it I was leaning back on Kyle’s jacket as he ate me out right there on the beach. Fuck, he was so goddamn good at what he was doing, it took me nearly no time at all to cum like crazy.

“That was fun,” he said with a grin when he was done and it was all I could do not to tackle him in the sand.

“I want you to fuck me,” I replied, as he took, my hand, grabbed his jacket and led me to the nearby lifeguard stand. We went up on the stand and made out some more, while I helped him undo his belt and he dropped his pants. I reached down and grabbed his impressive dick that was hard and ready for me, and before I could even try to put it in my mouth, Kyle had me bent over the railing of the lifeguard stand.

“Do you want me to fuck you?” He asked playfully. “Please,” I answered, and he slid in with one hand on my waist and the other with a fistful of my hair.

Holy fuck. His dick was perfect. It felt so goddamn good, and he had just the just right amount of force and rhythm that I came right away. I don’t always cum from penetration and I rarely cum when getting fucked from behind so I was impressed as hell. It didn’t take long before he pulled out and came too, and I was left nearly speechless. We kissed again and all I could really manage to say was “Goddamn.”

While I was still catching my breath, Kyle stripped off his shirt and said “I’m never out here by the beach, I gotta jump in” and he took off, completely naked, toward the water and jumped in. He was so much fun, the exact kind of guy I needed on my roster. Fun and spontaneous with a dick game straight from heaven. I gathered his clothes and waited for him to come back from the freezing water, he jogged up laughing and then used his shirt to dry off before throwing his jeans back on.

He kissed me again. “Can I give you a ride home?” he asked. I laughed and said “yes” and we were on our way. “I had a great time,” Kyle said as we pulled up to my place, “can’t wait to do it again.” One more kiss and I was off to bed, still buzzing from the sex, my serotonin levels so high it was like I’d popped some molly and I drifted off into a deep post-dick-down slumber.

Kyle and I went out a couple more times. I’ve never done heroin or anything, but I imagine it must feel like sex with Kyle did because that shit was amazing. Our between-date conversation was limited to making plans for our next dates, where each time it was as fun as the first. Drinks, great conversation, incredible, animal sex. It was fun and light and the exact perfect kind of friends with benefits situation I needed. After a while I stopped hearing from Kyle, our schedules were both really crazy and I was traveling a lot, so I didn’t really pay it any mind until I heard from him a month or so later.

He apologized for falling off the face of the earth, which to be fair I kind of had too, and said that he’d started seeing someone so he needed to behave. I fully respected that and there were no hard feelings. As most things do, our relationship had run its course and I was happy to have been able to experience it. But you better believe I’m keeping Kyle’s number just in case, because spectacular sex with a really fun guy doesn’t come along every day.

Meredith Actually is coming back in 2018!

After taking a couple of months off it’s time to revamp and reboot Meredith Actually!! Starting on January 1st, I will be bringing it all back and this time it will be better than ever!

-Ask Meredith posts every week: each Friday morning I’ll be answering your top 5 questions on my blog. Sex, dating, life, work, beauty–anything you want to ask me! You can email me at meredith@meredithactually.com or fill out my contact submission form here on my website. Your questions will always be kept anonymous and I’ll answer everything that I can!

-Bi-weekly sex and dating stories! I know you love my personal stories of dating and sex fails and triumphs and I’ve curated tons more stories that I can’t wait to share with you all! Look for the first story of the New Year on Monday morning to help heal your New Year’s Day hangover.

-Bi-weekly think pieces–I’ve got opinions and experiences and I want to share them with you! Something you’d like to see me write about or talk about? Email me your topics, I want to get conversations started!

-New Merch–I’m updating my merch store in 2018 and as always you can shop official The Meredith merchandise here and use my code MEREDITH for 15% off your order!

What else is coming in 2018?? More hoe tips, more dirty jokes, more stand-up shows and a podcast!! Keep your eyes and ears peeled, I can’t wait to share all of this and more with all of you, my little basuritas!

Happy New Year!

Xoxo,

Meredith

Sam

Being  somewhat of an Instagram personality, I get guys in my DMs (that’s “direct messages” for those unfamiliar) pretty much on a daily basis. The majority of the messages are some form of flirting, but usually from guys that, I’ll be perfectly honest, I’d probably never go out with. Truth be told, half the time I don’t even read my messages because I’m almost positive they’ll be something weird, a dick pic, or some foreign man asking to see my “bobs and vegana.” But then, every once in a while I’ll see a message from a guy who looks like there’s a chance he could be attractive, so I stalk his instagram account (if it’s public) and determine whether or not I want to answer.

 

Bro tip: if you slide into my DMs, make your profile public. You’re far more likely to get a response that way.

 

After a disappointing couple of days being let down by a couple of men I’d been interested in, I resolved to spend the Fourth of July alone on the beach, which was equal parts depressing and liberating as I love fireworks but people can be annoying. I was scrolling through my messages when a DM from Sam popped up. He was drunk and partying with his friends in San Francisco, but he lived in the South Bay near me and wanted to take me out for drinks when he was back in town. Naturally, I played hard to get and engaged in some playful banter while I carefully and methodically stalked his entire Instagram account to determine if he was cute or not. He didn’t have a ton of photos of himself and the few he had were mostly him making ridiculous faces, so I really couldn’t tell much other than he had the bald and bearded thing going on and appeared to be in shape, but I figured why not. At the very least I’d get some free drinks out of the deal and maybe a dinner and a friend.

 

Once Sam was back in town he asked if I wanted to go to Strand House in Manhattan Beach at 8pm. Not really my vibe, and since 8pm could be a drinks time or a dinner time, I casually asked “are you feeding me or should I eat first?” Sam laughed and said he’d be happy to feed me and suggested going to Fishing With Dynamite instead. Considering that’s my favorite restaurant in Manhattan Beach and I love oysters, Sam was already winning some points, so couldn’t help but respond so politely with:

 

“So are you actively trying to fuck me, or…?’

 

He laughed and said “well, yeah obviously” and we agreed to meet at 8. I never really get super excited about dates, perhaps out of self-preservation or just because I’m a bitch, but I was at least looking forward to oysters and possibly some dick. I threw on a casual beach dress and headed to the restaurant, which I arrived to early but Sam had the foresight to make a reservation so they seated me right away. I sat down and ordered a glass of sparkling rose’ (because I can’t be TOTALLY devoid of my basic bitch tendencies) and waiting for Sam to arrive. Just a few minutes passed and he walked in with a huge smile on his face. Sam was cute, not totally my type but I could see he had a couple of tattoos and seemed to have a cool chill vibe about him and the conversation began to flow as easily as it had in text messages. We ordered oysters and a bottle of the same sparkling rose’ I’d been sipping on to get started, and then another round of each, and then more food, and then when we were already tipsy and probably had no business continuing to drink we made the (probably) ill-advised decision to go to Manhattan Beach’s loveliest dive, Shellback’s Tavern.

 

Two pitchers of Kona Big Wave and my rousing rendition of Toto’s “Africa” while it played on the jukebox later, we began sloppily making out at the bar. Gross. I HATE when people do that. But also, when Meredith has had *just* the right amount to drink, her drunken alter-ego Jackie appears and Jackie gives even fewer fucks than Meredith does.

 

Hoe tip: Give your drunk self a different name so you can blame your bad behavior on your alter-ego and not take any responsibility.

 

The bar was emptying and I decided I was going home with Sam. Sam called us a Lyft and we were headed to his place in Redondo. As we’re on our way I begin to ask Sam about his living situation, like if he was in a house or an apartment or had roommates or what.

 

“Um…about that…”

 

Oh god. This was where the ball was going to drop. Not knowing where this was going next he began explaining to me that his lease had ended recently and he wasn’t moving into a new place for a couple of months so he was currently living at his grandmother’s house.

 

Yes. He was bringing me home to his GRANDMA’S HOUSE.

 

What the fuck. He explained that it was a split level house and he has his own entrance and total privacy but he was basically sneaking me in and out like we were in high school. Sober me probably wouldn’t have been too excited about it, but Jackie was drunk and horny and didn’t really give a fuck. So away we went to Sam’s grandma’s house.

 

Once in his room we picked up where we left off and began making out aggressively. As I was only wearing a dress with nothing underneath (I almost never wear a bra or panties) I was naked before I knew it and he was going down on me. I always appreciate a man who gets me off first because I’m not one of those women who regularly cums from penetration. Once I came it was sort of whirlwind of Sam getting undressed and we commenced the sloppy drunk fucking. Sam was pretty average size wise, but I was really too drunk to care either way and as we went from position to position Sam started with the ass play. I was totally down to get weird and gave him the green light, and just like that, we were doing anal on the first date. It wasn’t long before Sam was ready to cum, and I guess Jackie was really taking over that night because I told him to cum in my ass…so he did. Anal creampie on the first date, my mother would be so proud.

 

After the awkward cleanup that is always associated with an anal creampie, it was definitely time to pass the fuck out. After some solid drunken sleep, we woke up around 8 or 9 the next morning and Sam kindly offered me a ride home and some breakfast. I mean, a gentleman always buys a lady breakfast after cumming in her asshole, right? That like some kind of etiquette rule I think. I don’t know, cotillion was a long time ago. After sneaking me out past grandma and taking me to breakfast, Sam took me home and we agreed we should do it again sometime.

 

My summer schedule was all over the place and we were both in and out-of-town quite a bit, so we never really made it happen again and the appeal faded, but we’re still in touch and always laugh about the first date anal. While the majority of the guys who slide into DMs on Instagram are usually weird, creepy, or just not cute, don’t count them all out because every once in a while you find yourself a cute guy like Sam who takes you out to an expensive dinner, fucks you in the ass, and buys you breakfast the next morning. That’s modern romance, y’all.

 

Accidental Handjob

Back in my former life before memes and telling blowjob jokes on the internet, I used to work in sales in the craft beer industry. One of the many perks I had was getting to travel all over the United States for meetings and trips to our breweries, and my first big girl business trip was to a place I’ve grown to love so much, Portland, Oregon. Portland is basically just like my hometown, Austin, but with cooler weather and mountains in the background, so naturally I fell in love with it as soon as I arrived. It was gorgeous June weather and my coworkers and I immediately began exploring the city and hitting up local breweries. I’d only been single for about 6 months and I was excited to be on my first real business trip, so I hopped on Tinder just to see what I could find. I absent-mindedly swiped here and there for a day or two and came across a handful of viable options, including a super cute hipstery looking guy named Michael. He had sandy brown hair and blue eyes and looked so quintessentially Portland I had to message him when we matched.

 

I had some previous standing dinner plans later that night but Michael was really cute so I thought, why not go back to back and meet this guy for happy hour. I was down for something super laid back with good beer, so Michael suggested a bar called Momo’s and our date was set. I went on with my work day, stopped back by my hotel room to change, and I was on my way. When I arrived at Momo’s Michael was as cute in person as he was in his photos, and had a great and charming personality. He made me laugh, we drank a few beers, and I was laying on the flirtation heavily. You see, most all-day long work meetings can be pretty boring. But when you work for a brewery, you’re drinking during them. So I was definitely around 5 beers deep when I began the heavy petting. What can I say, I’m a classy girl.

 

We began making out a little at our table and I asked Michael if the bathrooms here were single-person ones or ones with multiple stalls, and he said it was a single-person one. I smiled with a look that I can only imagine would either strike fear in the heart of my mortal enemies or give them all intense boners, and said

 

“Perfect. Meet me there in 2 minutes.”

 

And like he’d been using stop watch, Michael showed up to that bathroom in exactly 2 minutes. I locked the door behind him and we went after it, making out, running our hands all over each other and he pushed me up against the sink. I was wearing panties for some odd reason (I rarely ever do this) and he reached up under my dress to pull them down. As he smiled and began kissing my thighs, I propped myself up onto the sink. Michael slipped my thong off, spread my legs and dove face first into my freshly waxed pussy and went to fucking town. It was so hot, the idea of getting caught, propped up on this bar bathroom sink, getting eaten out by this insanely cute guy. It wasn’t long before I was cumming in Michael’s mouth. Fuck, it was so hot.

 

Naturally, I went to return the favor, as is only the right thing to do. I undid Michael’s pants and pulled out his hard dick. Average in size, although not that it really mattered since I was just blowing him at this point. I put him in my mouth and it seemed like MAYBE a minute before he was cumming. I thought, either I’m just that goddamn good or this guy cums quick as fuck. I could tell he was a little embarrassed so I made no mention of the speed or anything, we got ourselves put back together and made our probably very obvious exits from the bathroom and got one more drink before I went off to my dinner plans. Michael was great and I really wanted to give him another shot before I left, so I suggested he stop by my hotel room sometime the next day for another round.

 

The next day, Michael came to my hotel room. Still cute as ever, and this time he seemed very ready to go and roll around a little now that we had some space. We made out for a while and he slipped off the shorts I’d been wearing around my room. Michael was apparently a pussy eating prince and dove in again. I laid back and enjoyed his tongue skills and after I came I reached down to warm him up before sex. Only, there would be no sex.

 

I pulled Michael’s already hard dick out, and within two tugs of a half-assed handjob, his body shook and my hand was full of cum.

 

I hadn’t given a handjob to completion since I was a teenager, nor had I ever experienced a man cumming THAT quickly and easily. I thought he was embarrassed but he just kind of laughed it off and said “oops.” What was this? Some kind of hipster retro handjob sex thing? Damn, hipsters really do have to do everything before it’s cool, including cumming apparently.

 

I awkwardly went to the bathroom to wash my hands and when I came back he was dressed and said “well, have a safe trip home.” I hugged him and said goodbye, and he left. Naturally I told my girlfriends IMMEDIATELY about the accidental handjob I’d just given, and started getting my things together to head home.

 

Maybe Michael cums quickly on a regular basis. Or maybe it was just me. But at least he was cute, funny, and he made sure I came first so I really can’t complain much. We’re still in touch and talk from time to time, he’s still cute, still funny, and still loves eating pussy.

 

Hoe tip: make sure you get yours first, ladies.

 

Jack

I grew up in Austin, Texas, but when my mom remarried when I was around 25 she moved to the Ft. Worth area. Visiting her is nice, but I hardly know anyone there so I get pretty bored during a long visit. That’s where Tinder and Bumble come in handy. I debated whether or not I wanted to swipe right on Bumble on Jack for a minute before ultimately saying “fuck it” and going for it. We were a match, and since Bumble requires the woman to make the first move I went ahead and sent a pretty generic “hey how’s it going” message, and he responded almost right away. It turns out Jack was also visiting his family and just as bored as I was on a Monday evening, and after maybe a few minutes of conversation we decided we both needed to get out of the house and get a drink.

 

Jack wasn’t exactly my type, I’m not usually into bald guys, but he had a great smile, had the whole cute Italian thing going for him, and he looked like fun, so I was game. I met Jack at a bar not too far from my mom’s house, close to Texas Christian University campus (oh the irony), and he greeted me with a huge smile and hug. I could tell he had a good energy about him as we started to talk and get to know each other. Jack was a professor at a pretty well-renowned university who would be spending a few months writing his first book this winter, so we shared war stories of the writing process, and commiserated over the struggles of writer’s block. I told Jack all about my Instagram and my blog and he was enthralled with my dating stories.

 

“I’m gonna do what it takes to make the blog,” Jack said with a smirk.

 

I wasn’t sure if he meant he’d do something terribly embarrassing or if he meant he was going to blow my mind, but either way I was excited to find out.

 

We decided the bar we were at was a little too dead so we needed a change of scenery, so after one beer we hopped in the car to find a more lively spot. After cruising around for a little while, laughing and realizing more and more that we were both total insane people, we pulled up to a dive bar that I can’t remember the name of and parked across the street. It was Monday, so everywhere was pretty dead, with nobody walking around, and before we got out of the car Jack said “I need to kiss you first.” We made out in the car like teenagers for a few minutes, and I knew the rest of the night was going to be fun.

 

Once we finally stopped acting like we were 16 and on a date to the movies, we went into the dive bar and had a couple more drinks. I almost never wear a bra or panties, and this night was no exception. Jack noticed and ran his hand up my inner thigh under my dress, right there at the bar. I tossed back the rest of my drink, looked at him and bit my lip. He smiled, leaned in to kiss me, and kept going with his fingers, teasing me under my dress, and then asked the bartender for his check. It was most definitely time to go.

 

We hurried to the car where we got in and realized, oh shit. We are BOTH staying with our parents right now. Jack was driving his dad’s car, and we couldn’t go back to either of our places, so we had to improvise. Jack drove to a dark parking lot nearby and we crawled into the back seat. It was only at this point that I noticed that the radio had been on this late 90s alt rock station, which only added to the high school nostalgia of the entire thing. Jack and I started going at it, aggressively making out, and he laid me down and pushed up my dress and started devouring me like I was his last meal. It was so hot, and just as I thought I’d cum soon he ripped off his shorts, revealing quite an impressive package and he slid in. He was just the right amount of rough, pulling my hair, lightly choking me and pretty much fucking my brains out. I came hard and as soon as I did, so did he, without missing a beat or even pulling out. While I realize getting cream pied on a first date isn’t exactly the smartest or safest thing I’ve ever done, it was so fucking hot I didn’t care.

 

Hoe tip: if you’re gonna make reckless decisions, at least make sure they’re fucking fun.

 

The windows of Jack’s dad’s Honda Accord were fogged up, R.E.M.’s “Losing My Religion” was on the radio, and I was getting railed out in a back seat in a dark old parking lot. If that doesn’t bring back some teenaged memories, I don’t know what does. We fucked a couple more times (shout out to Jack for having outstanding stamina), and then decided it was getting late and we needed to get home. Jack drove me back to my mom’s house, which just so happened to be in the same neighborhood his parents lived in. We pulled up to my mom’s house, Jack kissed me one more time, and as I got out of the car I said “oh, you made the blog.”

 

Jack drove off, and I snuck back into my mom’s house with cum dripping down my inner thigh, really rounding out my trip down memory lane. I hopped in the shower, and laughed at myself the entire time in there, grabbed some water when I got out and crashed. Jack and I are still in touch, and I’m sure we’ll see each other sometime when we’re both home for the holidays. Can’t wait to make another mess in the back seat of his dad’s Honda Accord.

Andrew

There’s something hot and exciting about a cute guy on the other side of the country wanting to fly you out for a weekend getaway. Promises of nice dinners, maybe a day at a spa, and lots of hot sex—sign me up! That’s what Andrew had offered me repeatedly, but since I only knew him on the internet, I declined. I mean, sure, I’d flown halfway across the country to meet a guy for the first time before, but I took my time vetting Andrew to make sure he wasn’t some sort of Patrick Bateman about to murder me. Andrew followed me on Snapchat for a long time, messaging me here and there, always flirtatious, and I would flirt right back. He was cute, but not really my type—a little too clean cut for me—with blonde hair and blue eyes. The kind of guy who definitely wore pastel Polo shirts with khaki shorts and loafers, but he had a nice body and I won’t lie, his bulge pics were impressive. He regularly asked if I’d like to come visit him in Boston, but I took my time getting to know him.

 

Over the course of several months I learned that Andrew was an accountant for the Navy, lived in a nice area in Boston where he had moved to from Virginia. He and I added each other on Facebook and he offered up any information I asked of him. I began to feel comfortable with him as a person and started to consider his offer to go to Boston. I figured I would make sure everyone knew where I was, and if I began to have a bad time then I could always leave or make friends in Boston and explore the city on my own. I was no stranger to enjoying a city on my own or meeting new people, so I thought I’d roll the dice and take him up on his offer. Andrew and I agreed on a weekend in July and he booked my flights for me. He told me that we would go out to Nantucket or Martha’s Vineyard one day and that we’d have a great time. He also said that he may have to work a little bit one day, so he’d gladly send me to a spa while he was busy. I was totally excited about my weekend trip and when the day came for my 6 hour flight I was more than ready for an adventure.

 

I arrived in Boston on a Thursday night and Andrew said he was outside waiting for me in his Audi. Nice car choice, Andrew. I was nervous and excited as I walked out of the airport and quickly spotted him. He was a little shorter and skinnier than he’d appeared on Snapchat and in his pictures, but I guess we all know our angles. He helped me with my bag and we were on our way to get dinner. It was a little awkward, he wasn’t outwardly affectionate, but he was very complimentary, telling me how sexy I was and how he couldn’t wait to get me home. We finished dinner and headed back to his place. When we walked in the door I noticed it was a pretty big space and he mentioned that he had a roommate. I asked if his roommate knew I would be there and he laughed and said “Shit I probably should’ve mentioned that to him.”

 

I thought it was weird he hadn’t told his roommate that he’d have some girl staying with him for the weekend, but maybe they weren’t close or maybe he knew he wouldn’t care. I don’t know, I was just ready to have fun. We went into Andrew’s room and got situated and he started to kiss me. We began to make out, which was decent, and he started to feel me up a la high school make out, before moving on to removing my clothes. As things started to heat up and we lost more and more clothing, I noticed that his dick wasn’t as big as it had appeared in his bulge pics.

 

This, my friends, is called cockfishing.

 

The dick didn’t match the pics, but it was relatively average. Andrew grabbed a condom and we got down to business. We pretty much just stayed in missionary and the sex didn’t last all that long, but I did manage to get off so it was fine. Almost immediately after finishing and tossing the condom, Andrew fell asleep. I was still on west coast time and it was only like 9pm so I was bored and just messed around on Instagram until I crashed out too.

 

The next morning Andrew woke up early and went to get breakfast for me before he had to go into work for a little while. I didn’t mind because I was a little jet-lagged and needed a nap, plus I had some work to do on my computer. It was raining in Boston so it wasn’t like I wanted to walk around the city, but Andrew was kind enough to leave me some cash just in case I felt like going to do something solo. Because of the weekend’s weather, we were no longer going out to Nantucket but he said we’d do fun things in the city. I was a little bummed, but I couldn’t do much about the weather. Later in the day he was finally headed home and asked what I’d like to do that night and if I wanted to get dinner and drinks. I said yes.

 

Andrew got home and seemed a little off. I was ready to go to dinner and he was quiet and not as complimentary as he had been the night before. Finally he asks me, “What did you snapchat today?”

 

I looked at him with confusion and racked my brain. I hadn’t snapped anything crazy, just a few shots of me with stupid filters on saying that I was in Boston. He told me not to snapchat from his house anymore, which was confusing and weird. I asked what was up.

 

“So, I’m dating someone. And it turns out, she follows you. She recognized my bedroom in the background of your snaps.”

 

Motherfucker.

 

He quickly tried to do damage control and tell her that I’m just a friend crashing with him for the weekend and that it wasn’t anything to be worried about. But then he told me what her snap name was and said not to open any snaps from her if she messages me. I asked if it was exclusive or what the situation was, and as he tried to downplay the relationship to make me be cool with things. I began to realize that no, this guy is obviously a liar, and this wasn’t okay. He then proceeded to go into his living room and ignored me for three fucking hours, like as if somehow any of this was my fault.

 

Hoe tip: when a guy gets caught cheating on his girlfriend, it is HIS fault.

 

I had received several messages from people in Boston wanting to hang out and I got on Bumble and said fuck it, I’ll find someone else to hang out with this weekend. As a few hours went by a guy I’d talked to several times in recent days, Jay, offered to pick me up and at least give me somewhere else to crash for the night since it was late at that point and Andrew hadn’t even had the common decency to feed me dinner (after feeding me bullshit, that is). I texted Andrew from the next room and told him I was leaving. Andrew came into his room and asked if I was sure, and I told him that I was really uncomfortable and didn’t want to be there anymore. He gave me a half-assed apology, Jay showed up, and I was on my way.

 

Jay took me for a drink and a bite to eat with his friends, and gave me a place to crash for the night. He showed me around Boston a little the next day, and then we went our separate ways. I set off to meet a guy or two from Bumble, after, of course, Jay decided to go out of his way to tell me that I don’t contribute anything to society and that I’d be cuter if I took better care of myself. Like completely unprovoked, he felt the need to pinpoint everything he thought was wrong with me. The next guy I met in Boston, Adam, was all fun and great and invited me to drinks and dinner with his friends, but ditched me after drinks to wander around south Boston alone. I got myself a room, had a good cry, and crashed out.

 

Finally it was Sunday and it was time for me to go home. I couldn’t wait. I got to the airport, got on the plane, and got shit-faced. Andrew had bought me an upgraded seat that included complimentary alcoholic beverages, and I took full advantage by drinking all the prosecco they had on the plane. As I was crushing drinks I thought about all the people I had encountered over the weekend. Every guy started out with promise and just wound up being a typical, immature dick. What kind of vibe was I putting out there that I was attracting these guys? I mean, sure I portray myself in a certain way, but that doesn’t mean I’m not still worthy of respect as a human being. Andrew probably assumed that because I’m a sexual and open person, I would be okay with facilitating him cheating on his girlfriend. And Jay probably thought that I somehow needed his advice on how to live my life because I’m a woman and therefore inferior to him (I almost sprained my eyeballs rolling them so hard). And as for Adam…well I think he just got drunk and forgot how to treat people. At the end of it all, these men were immature and lacked respect and that wasn’t my fault.

 

I don’t think I’ll ever be making it back to Boston. Although I’m sure there are plenty of lovely people there, I only met Massholes.