[MF] During a Biz Trip To NorCal About 2.5 Summers Ago, I (34) Take 19 Year Old Barista’s Anal Virginity

So this happened during the Summer of 2014. I was going up to the Carmel/Monterey area for the Concours D’ Elegance Automobile weekend (fiasco). Those that have been know it’s about the best gathering in the world for fine/rare/exotic automobiles. 5 days of amazing cars, women, fashion and parties.

I wake up (Thursday) the morning after i drive up from Southern California a little groggy and still peeved after I was 6 hours into the 8 hour drive the night before and get caught doing 113 just trying to get to my damn hotel by dark (thank you CHP for not arresting me!) I am hungry so i head to this restaurant/brewery behind the famous Monterey Aquarium and post up for a drink and burger. As i’m sitting there at the bar, a guy about my age strikes up a convo and says he works for the DuPont Registry and just got into town as well for the weekend. Mentions he has an extra ticket or two to the Playboy party in the Harbor Thursday night on Al Capones old yacht. I’m thinking, this is a great start to the festivities. Take his num and told him I’d hit him up the next day, and head over to check into my hotel in Carmel and get some much needed Z’s.

I wake up about 7a and had remembered from the year before there was this cool little coffee/espresso place in town so i stopped in before i headed to one of the many auto auctions to get the cars ready that i had brought up to sell. As i’m waiting for my dry Cappuccino, i must had been half asleep and fixated on this brunette that had her back to me behind the counter, and was grinding some coffee beans. She had on a white sweatshirt and nice and form revealing blue jeans. As I’m gazing at her amazing ass, said girl stops grinding beans, goes over to the espresso machine to steam milk, then turns around hands me my drink. I was pleased to see that the face was as nice as the ass :D

J: About 5’4″, Medium Brown Hair, Hazel Eyes, 120 lbs-ish, 34B-ish boobs.
Me: 6’3″, Sandy Blonde Hair, Blue Eyes, 170 lbs (lean/runners build).

I thank her, and ask her name, and she says Jamie (changed for this story). I decide to sit down to buy some time and figure a way to ask her #. After a couple minutes of this, i stand up when i see she is back to grinding beans and walk over. “Excuse me Miss, I just wanted to thank you for the great Espresso drink. And by the way, do you mind if take down your number? I’m only in town until Monday, but would love to take you out to dinner before i leave.” Surprisingly she responds, “Sure, that would be fun.” I grab my phone, and head off to the Hyatt Hotel to work the rest of the day.

It was not even noon yet and i was already thinking about J. So i decided to text her. She responded about 20 minutes later and said she was on her break, and that it was nice meeting me earlier. Eventually I got to ask her to the Playboy party that night. She responds, “Heck yea, that sounds awesome.” She then states, “You know I’m only 19, right?” Fuck, I knew she was young, but i didn’t think she was THAT young. I then call my new buddy that i had met the night before asking him if i could get 2 tickets. He said, “Yea, I got you.” He then texts me a pic of the tickets, and i notice the dreaded statement, “21 And Up.”

Now I’m in a predicament. Playboy party on Al Capone’s old Yacht or date with hot 19 year old local. (Insert, Choose Your Own Adventure book) I then decide to choose the adventure with the 19 year old local.

I break the news that unfortunately it’s 21 And Up, and she is bummed. So i go out on a limb and ask if she’s up for coming by my hotel and we’d go to dinner and look at some cars at the RM Auction at the Portola Hotel in Monterey. By this time it’s getting late in the afternoon. The Summer fog is starting to come in. She says, “Great, I am going to meet my girlfriend for dinner and i’ll head over to your hotel after.”

I leave the Hyatt a little late and stop by the BevMo in town on my way and get a bottle of Crown and a bottle of Coke. Sounded good on a damp Summer night. I drive the short drive back to my hotel, run up the stairs and it’s not 2 minutes i’m in my room, i get a call saying she just parked outside (it’s a small town & country type hotel with 2 stories). I was hoping to be able to shower atleast before she got there. She comes up and is in a really nice black flamenco-type dress, with dangly ear rings, hair down, with turquoise blue heels. (Dress: http://imgur.com/a/J6G09)

I invite her in, we exchange hugs, I am loving her outfit, and i tell her that i am going to hop in the shower and to make herself at home. I was surprised for a 19 year old to be carrying herself so well. Not ditzy, not overly outgoing, not shy, knows how to dress, etc.

I come out of the shower and she is sipping on a flask she brought. I was rather surprised by this, but didn’t necessarily stop her. I jump in some black chords, a brown long sleeve shirt, and tan/brown Cavalli shoe’s a sugar momma had purchased for me the year before on a trip to Rodeo Drive :)

We were at my room for a total for 15-20 minutes from what I recall (just enough time to exchange pleasantries, shower, dress, and guzzle a stiff Crown/Coke) before heading to the Hotel Portola around 730p.

(Album For Those That Like Cars: http://imgur.com/a/drTZ3)

We get there, and the lobby is filled with great cars, and beautiful people. We walk around for 30 minutes or-so, then i see my friend who works for RM. She waves us over and i ask if she has any passes for the auction inside. She hands us 2 and we walk in and look around for a bit. We had probably been there for an hour, and by this time i was getting hungry and craving Sushi.

I ask the local if she knows any good Sushi spots in Monterey and she says, “Yea, but hopefully they are still open.” If anyone knows Monterey, it’s a pretty sleep town.

It is closed so i look on Yelp and find a place that’s open til Midnight. I mention the name and she chuckles, “That place is kinda dingy, but atleast they’re open.” We drive the short drive and walk in. She was right, it looked like a restaurant you’d find in a back alley in Tokyo or something (black booths, fish tanks, cooking supplies and to-go boxes all over the place), but hey, it was 10p at night, and the only thing open, and i was with a fun and hot 19 year old. I could care less.

I was drinking Sake and had a couple drinks at the Portola, so i was feeling pretty good. As we sat across each other in the dim lit booth, we were having good conversation, getting to know each other, and our families, upbringing etc. Then she mentions that her mother is quite a bit younger than her dad and they are still happily married. A little light went off in my head. I think, “Okay, that is probably the reason why she didn’t have a problem with the age difference when i asked for her number.” Although I have been told numerous times that i could pass for being in my mid-late 20’s.

By the time were were done eating, we were both pretty tipsy. She had finished her flask and i was 4-5 cocktails in. The topic turned to sex, and we were talking about our experiences, likes/dislikes etc when the topic of anal came up. I forgot exactly how, but i think i just briefly mentioned that i enjoyed ass fucking and asked if she had ever tried it. Her eyes got big, and she said, “Noooo”. BUT, still had a little grin on her face like she wasn’t offended that i asked it. We didnt’ talk too much about it, but i knew all i needed to know. …………………………………………………………………………………..

By this time it was 11ish I’d say so we asked for the bill and headed back to her car at my hotel. When we got closer, i asked if she’d like to come up and she said, “Sure, why not, you’ve shown me a good time tonight, but i can’t stay the night because my mom will wonder where I am.” Wow, okay i thought.

We head up the stairs and it was basically right to business. She sat down on the bed, tossed her purse off, and I whipped off my belt. Not sure of her experience, i pulled down my boxers. Now this night couldn’t go perfect all night right? And i hit a little snafu. While i wasn’t thrilled by her bj skills, i wasn’t getting hard. Sake dick had kicked in. Not wanting to waste this holy experience, I pressed her back on the bed, lifted up her dress (to expose the nude thigh-highs she had on, which I particularly enjoy on women), slid her thong to the side and started eating her out. It was one of the nicest shaved pussies i had seen in a minute. When she started moaning, i felt blood rushing to my cock, and after about 5 or-so minutes of eating her out, i was ready for action.

I picked her up and moved her a little further back on the bed, and mounted her Missionary and she told me to go slow because, “You have a big cock.” I dont think i’m that big, but i’m a thicker 6.5 to 7 inches, so i took it as a compliment. After she got used to me thrusting in and out, I did what any sensible guy would do and flipped her over Doggystyle. Now atleast in my books, there are not many visions better than a 19 year old in thigh-highs and heels, face down ass up on a bed.

I started fucking her from behind enjoying every second of it. I grabbed her by the hair and started fucking her a little harder and i heard her wimper, “Yes, fuck me harder.” So i began to thrust harder, and her moans got louder. I started pressing her asshole with my thumb to see if she was comfortable. No protesting. After she got used to that, i started slowly pretty my thumb inside her ass expecting some protest. Nothing. After a minute or 2 my whole thumb was basically in her asshole. I started feeling like i was going to cum, so I told her, “I think it’s about time to get fucked in your asshole, what do you think?” She responded, “Yes, do it.” I pulled out and my cock/condom were so wet from her pussy, i didn’t feel the need for lube. I started pressing my head against her asshole and felt the pop. She yelped a little, but nothing crazy. I took my time and pressed my self all the way in paying attention to any discomfort she may be having (guys alot of times rush things or dont do anal properly, and it sucks because it ruins it for the rest of us that do. Sometimes i feel compelled to write a book on the topic: The Art of Anal). She was doing well, and before she knew it, all 7 inches of my cock were filling her ass. Once i was in, i started thrusting harder asking her how she felt, and she responded, “God that feels good, so full but so good.” Her deep moans were turning me on so much that after a few minutes i was feeling the urge to bust, but i didnt’ want to yet, so pulled out and switched condoms and started fucking her pussy again.

I put my thumb in her again while i was fucking her and this was when i started to hear/feel her tense up. If only i knew what was coming next. She started squirming, ass/hips twitching up and down and she lets out loud yelp/moan/yell and i feel her asshole pulsing around my finger. She had just had a crazy orgasm and i pulled my cock out to see a stream of fluid shoot on the comforter. Her hips were still shaking, and i was so turned on, that i stood up on the bed, ripped the condom off, and told her to get up on her knees under me. It took her a few seconds to get her composure, and by the time she was under me, tongue out, I blasted her face and tits with a 4 day old load. Covered. Her eye-shadow over her eyelids looked so classy covered in cum, i’ll never forget it.

I collapsed back down on the bed, we both laid there laughing and cuddling and were probably both realizing what a night we had just had and how crazy it transpired to be.

By this time, it was 1 or 130 and she had to get home true to her word, so we cleaned up, i showered, and got in bed still thinking i had just dreamed the past 18 hours. I texted her to make sure she got home alright and she did, and she snuck in to make sure she didn’t wake up her parents.

The next day, back at the Hyatt, i was daydreaming most of it away, thinking about the night before. We were texting and i still couldn’t believe i took her anal virginity. So i asked her again, “Are you serious, that was the first time you had anal sex?” She said yes, i promise. I’ll probably never know 100% but i have to take that at face value. Either way it was an amazing way to start Concours weekend 2014. I have not been up since 2013 and 2014, but i may be back up this August, but it is hard to imagine i could top 2014.

I had a lady friend that had planned to come up Friday night from SD and stay Friday/Sat night but i didn’t tell J that. I didn’t think I’d probably see her again. But low & behold, i get call from her about 630p the next night. I was getting ready to go pick up my friend from the Monterey Airport because her flight got in around 730p i think it was. J said she was with her girlfriend and was wondering if i wanted them to stop by on their way down to a party near or in Big Sur area i think it was. I couldn’t believe it, I was trying to rush out the door and this girl wants to come by with one of her friends. I didn’t want to tell her i had another girl coming up for the weekend, so i just told her my Aunt was coming up for the Shows and she was really into cars and we had to go to a party in Carmel that night. She sounded disappointed and said something like, “Oh, okay well i guess i’ll talk to you later.” I was so mad. I was mad at a situation i could not change, and i probably wouldn’t see this girl again.

As i pulled up to the airport, i was so agitated that i wanted to kick a hole through the firewall of my car. My friend got in and while it was good to see her, I could not get the thought out of my head that i could be back at my hotel with TWO 19 year olds, very likely having my way with them. Apparently she could tell something wasn’t right because 5 minutes from the airport she said something to the effect of, “Are you okay? You seem like something is bothering you.”

If she only knew.

Source: reddit.com/r/gonewildstories/comments/5u31f0/mf_during_a_biz_trip_to_norcal_about_25_summers