How I Lost My Virginity to a Boy 

Great story... not only did you win your award you literally got your cherry on top!

How come I didn't get to experience any trips like this while I was in high school lol? Damn.

Don't listen to all the complainers ! You never can please everyone. I liked the story and certainly was not bored !

Thanks for being so open and honest about your experience. It wasn't boring at all in any way.

Just remember to keep condoms with you at all times that type of play while drinking is DANGEROUS.

That was a great video. Everybody’s first time isn’t the best. But look at it this way. You seemingly enjoyed the 25 minutes, so it wasn’t that bad. But it’s a great milestone. And also bottoming for the first time isn’t easy and you appeared brave. It didn’t really rob you being the worst time ever. And you’re safe and back home. You should feel good about your first time. It lacked passion, but it wasn’t horrible. Also, you have to imagine the other person’s feeling. That might have been his first time too. I don’t care what he told you. I’m new to your channel and place al of your videos into one of my binge fines so that I watch they all later. You have an innocence about you that I hope you never lose. So remember to continue to hold on to that. And never rush love. That person, your person, will come to you when you least expect it. In the meantime, I hope you have a wonderful long and happy life. You’re very handsome, and I’m sure your door is already being knocked on, for sure. One last thing, I love that bed you have and the very room looks large. I want a King Size bed, so finding a place to accommodate on is hard to find. My have to keep the Queen. On that, I absolutely love the place I’m in and don’t have to move. Oh, you want me to talk about my first time, I will,, but I don’t have a RU-vid channel. But it was a blissful threesome. And it was life altering. I stayed there for an entire weekend. I turned 18 on that Monday.

Had a similar situation happen to me at my ffa conference and it was when I was 17 too. It was just as special to me but it did make a definite stock in my growth to being the person I am. Stay yourself and stay positive.

Love how your stories are so detailed, that keeps them interesting...

A good job telling the story. Maybe a little too much repetition across the edits. You're coming across as sweet and genuine. Stay that way!

Ritchie, It's great that you won the first place. I suspect very few guys' first times are like what we hear about in about in romance, or pornagraphy. I'm glad your first serious time time with a guy was good, and safe. We all learn as we go

Richie, this is an incredible coincidence: I experienced my first penetration at a state FBLA convention/competition, too. That was in 1977. Not only that, I won my category, as well. Unfortunately, inexperience on both our parts caused me to suffer an injury that took weeks to heal. Of course, I could not seek medical treatment for it since I had to keep my sexuality a secret from my family.

Thanks for sharing that with us. I hope you will take your experience, and when you find a virgin you will explain to him what you know. So he will find his first time something he can remember the rest of his life, just like you did.

Thank you for being so open about your life. There is no shame to your experience and don't let the brain-dead church people out there make you feel guilty about your first experience with sex and being willing to share it with others. Just know that you are the stronger, you are living in the real world, you are courageous about your life. No shadows, no shame, a realistic attitude about sex which will be with people the rest of their lives. Being gay and having to hide it until my 50's within an 18 year marriage with four children makes me recognize what is real and what is based upon 15th century moralism. God gives sexuality to people and God is diverse and sexuality is diverse. Amen!

Oh the memories, never forget them because when they're good they're good... I like your story and the way you tell it, I feel that your such a genuine and kind person that you could probably tell a story about growing grass, and I would listen LOL.. although you are not my type really there is something very endearing about you. Thanks for sharing.

The story was quite interesting. Thank you for being so open and sharing. It is interesting the things people do in secret. You do you. That is the best you can be.

Neat story! So cool that you made it to that competition and won first place! Your hard work paid off...in more ways than one...hehe ;) What a great field trip :)

I remember my first time with a boy, at first I was shocked, and didn't want to speak to him again, I didn't know much about him in the first place. Long story short, a few years later I wondered about him, but he just faded away. I think he was just curious, but it was a one time thing for him.

Better than my first time keep your vids going x

It sounds like you won and you had a good celebration. Nothing to look back upon sadly. It’s a good teenage memory

Congratulations on both accomplishments! 🙂 I enjoyed the story and thought it was fun and easy to follow nice job! I wish I was forty years younger! 🙃

Hey, enjoyed hearing about your encounter. That's life. Enjoy it!

You are so relaxed and unproblematic that's actually unexpected

I really like the way you have decorated your bedroom!

I think you could say you marketed yourself

I want to hear the other guys ..story..lol...👨🏻‍🤝‍👨🏿

In lieu of your first time experience which was a great story by the way I'm very impressed of the award that you want and I hope that you are able to continue to strive for the best and all that you do. But I did love the hotel story LOL

You accomplished more than you expected. Great!

Well, i liked the story, the way you telling it, and you look cute. Guess I'm subscribing 🤷🏽‍♂️

Nice story that rekindled stories from my youth, albeit a long long time ago.

I give you so much for for being yourself.

Dude, that was a LONG drawn out story.

Like you, I lost my male bottom virginity at 17. I was a freshman in college (we met in speech class). He was a senior (21). Unfortunately, it was a short-term relationship (six weeks (at most)). I wanted longer; after all, it was my first, and I didn't know about one night or a weekend stand. Two problems were: 1) He wouldn't switch. 2) He only had boyfriends when specific girls weren't available. A girl means he drops the guy right away. (It was 1974, BTW.)

Hotel lotion?! Omg! At least you didn't just use spit, lol!

You have a great talent for making a short story long!

Your videos are so incredibly sincere - very easily one of the BEST parts of RU-vid. Fantastic!

Ngl... I wish Richie was my boy next door...

I love your story times

The story was fascinating but the actual experience sounds as if it might have been a bit of a letdown.

Sometimes unexpected things happen and it turns out to be not so bad :-)

do you think that boy will ever come across this video ? :D

I lost my Cherry in the back of a police car 1976 RIP Cherry

I am glad your vlogs are suddenly coming up on my feed. Well told story, enjoyed it. Had no idea you were from MD....I lived in Frederick County 1996-2001 and loved Maryland. One of my daughters still lives in the DC area. Best!

Thank you for sharing this with us

Amazing channel Richie!! We have just bumped into it! We have just sub! Loads of love from two fellow youtubers!

Hotel lube is the go to !!!!! 15 mins is, by the way, a long time playing around. You did good for a first time !!!!!

Love the ginger hair 😍😍

So why did your friend/roommate have his mother come and take him home?

Richie so young thank you for your story. Nice smile

Wow! That is an impressive award to have won Richie!! And what a crazy field trip experience you had. You were a bit of a wild man in high school.😊😊. I bet this kid has fond memories of this school trip as well. Great story!! Thanks for sharing it.

When you hung your head I cheered! We had to opposite reactions... 😂😂😂😂😂

Hi Richie you look great and your first time experience was very interesting and you probably looked back since and enjoy guys.

Thanks for sharing Richie

My first time was amazing the guy was a perfect gentlemen. And afterwards we cuddled for about 3 hours. Wish I could see him again

thank you for sharing your story ....you are so very handsome ...enjoy your day

Nice video explaining about himself

Similar story. I lost my gay virginity kinda young and was a gold star for a LONG time. Then I lost my straight virginity. It was okay. Kinda mundane. It didn’t have that electricity. I don’t think I am bi. I just say I am open.

Sound like a good field trip.

OK, let's be honest! How many of you (like me) had to fast forward before the ice in your drink melted?

He was levels above you…and used hotel lotion? 🤦🏻‍♂️ Trust, he wasn’t that many levels above you. Also, I forgot I was in FBLA until you mentioned it 😂😂

Hello thanks for your stories VERY NICE

And three commercials later...

hope since then things have gotten better for you

5:59 Details are great, forget the impatient.

How sweet. I've had a few virgins and I always show them a really good time and teach them

You stole something very precious from yourself that you'll never be able to get back. Very sad story.

I’m a red head too and you’re the first red head I’ve ever thought was so cute and handsome

Love this. Have you found the perfect bf??

Interesting story. Just want to point out - there can be only one time you can lose your virginity to a boy ( or girl ). Unless you are like me - I didn't lose my virginity, I mislaid it.

Did he wear a rubber at least?

8 minutes in, still hasnt got to the story

Good job !

Oh, congratulations on you winning, I guess you can teach us about the market and finance.

Nice that you flat out stated, who was in what position (vs leaving us hanging). I wonder what his opinion of the experience was? Was he safe, or just blow where he wanted, putting u at potential risk. interesting to hear ur details. I assume u guys were both H.S. age.

I guess the boy was the one that stuck.

Strange the same thing happened to me not exactly but my first time I bottomed did know how and it all went good in the final result but I to did not or did not wat to see the guy again. He was gentle like he knew it was my first time and he knew it and wanted to enjoy that reality...even though a couple times I pushed him off me because I had the feeling I had to use the toilet but was a false alarm finally it was he could go no more deeper, and we paused for a moment and I got so exceeded we both lost control of the situation and the act of two young gay men do together was done. We were there another 15 or 20 minutes in bed and I left thinking I really don't think I want to see this guy alone again and seen each other again just never hooked up again,

6:24 Quantity over quality now so there might not be too many grand hotels (Disclaimer: Spoken from ignorance).

Couple things - WHY THE FUCK was there 3 commercials for a 13 minute video - FUCKING RIDICULOUS @RU-vid Number two - Totally new this dude was the bottom soon as he opened his mouth...LOL Number three - How nice is that bed? and headboard? Number four - Who else fast forwarded to the last 2 minutes to get to the point...LMFAO??????

So, Richie, are you now an experienced cute gay guy? Are you still single?

YT genre: how I lost my cherry.

So I guess you never found out exactly why the guy left early under such odd circumstances? Great story all around though.

Well it’s out now.

Let me guess, he split you in two?

Please get to the point

So afterward u just went your seperate ways u didnt talk about what happened did u enjoy it or no

How the fuck did best ice hockey cross check videos lead me here?

Enjoyed your story

Take care of yourself.

Were you rambling? Yep...you were rambling a bit! 🙂

You know, this is only the 2nd video of yours I've watched and you have got to learn how to edit yourself. You take way too long to get to the point and people will lose interest and click off.

Why are there no bedside lamps?

9:14 ...Just a thought, what if he lied. Hooked up with someone who could take him back.

We need more talk about the sex part! How big was he? Did he go easy with you? Fortunately my first wasn't very big because I hadn't learned how to relax yet either and he was older but was very nice to me. Anyway, glad you put that big single bed to good use. I thought you were going to seduce your original roommate on the bed! So now I'm rambling just like you did.🙂

Which Maryland village did you grow up in? Somewhere on the Eastern Shore?

Yeah man...any trip where you get laid is always fun! Your hotel mate probably knew you where gay, was afraid and called his mommy. Not me, I would have been lovin that...sleepin next to a hot redhead. Things would have happened, lol!

Hope you were safe.

Seems like you won two prizes

Sadly No it wore out many years ago and it was discarded. Those wree good days.

Well that was 13 minutes and 31 seconds of my life I'll never get back...

Honesty is very sexy. And you've got it Babe. I wish I had a boyfriend just like you.

Too many ads.😕