Teasing my old high school friend [FM]

This is a LONG confession so I apologize in advance!

In the past, I never noticed, but my friends were always telling me that I naturally teased guys with the stark contrast between my sexy figure and my genuine innocent personality. My figure made regular clothes very sexual, and I wasn’t really aware of it until recent. I would be happily sucking away and deepthroating on popsicles with happy sighs without realizing what I looked like (don’t laugh!). I’d bite my lips and moan in frustration when working on problems. I’d even get down on the floor (face down ass up) to grab things with no consideration as to how my ass looked. I was really naive. Like so naive that if you didn’t know me, you’d think I’m just messing with you.

Despite all this, I thought they were full of shit. I still had major body confidence and self esteem issues, and I thought they were saying that to just make me feel better. Me, sexy? A tease? HA! I wished. I did continue to wonder though. That’s why this past summer, I came to the conclusion that I needed to go a little outside my comfort zone. I decided that I was going to take a baby step and try some simple intentional teasing. Maybe my friends were right. I just needed to put things to the test.

Since I was back home, I found the perfect target. It was one of my old theater friends from high school that we’ll call Mike. He’s always defended me since middle school because he really appreciated how I always stuck up for him when so many people bullied him. He is super sweet, real dark sense of humor, and just a nice guy overall. It’s a shame I’m not attracted to him at all, but he’s just not my type. He invited me out to hang out with him, so I said sure!

Now he has a really nice circular pool and it’s blazing HOT, so I wanted to go swimming when he offered. However, I realized the day of that I left all my bikinis in storage (stupid I know) and didn’t really have time to get a new one. He would be here real soon. I was super bummed. It’s not like I could go swimming in my bra and underwear, right? Wrong. Oh so very wrong.

Mike picks me up a couple minutes later. He surprises me by taking us out to this delicious breakfast spot. He knows how much I love food. We chat and eat for about an hour before we head to his house. It’s the moment of truth. I’m extremely nervous, but tell myself to just stay calm and enjoy myself. When we get to his backyard, I start taking off my clothes. Underneath is my lacy black thong that left nothing to the imagination with my tannish floral push up bra suffocating my boobs. Mike turns around and his eyes widen.

Mike: “What are you doing?”

I look at him with a confused look. My theater skills are coming back to me.

Me: “What do you mean? I’m taking off my clothes to go swimming.”

Mike: “Um…. what are you wearing? It looks like you’re in your bra and underwear.”

I had anticipated for this.

Me: “Oh Mike, I’m such an idiot. I left all my bikinis back at college, my sister is on vacation so I couldn’t borrow hers, and I didn’t have time to buy one at the store. I really wanted to go swimming so I just put on my old middle school bikini. You know how I am. I know it doesn’t fit very well and it looks like lingerie, but it’s not.”

This seemed like a logical explanation coming from me. No one would ever doubt that I wasn’t being honest.

Mike: “Oh ok. Sorry about that. I guess I’m just not used to the style. Let’s jump on in!”

He waves me over with that goofy oblivious smile of his as my plan goes well. He was staring at my body the entire time while we just played with his cute dog in the water. I was dying of laughter and it was just really fun. I teased him the whole time. I always wore things that covered me up in high school, so this must have been a drastic change for him to see. I would make sure to bounce in the pool so my boobs would jiggle. Biting my lips and sighing from how nice the water felt. When I left the pool to get something, I would make sure he could see my ass perfectly. He started off really well.

Mike: “Hey… umm… I think you have a wedgie because your ass is all out. I just wanted to let you know.”

Me: “Oh that’s so embarrassing! Thank you Mike. You’re great. I really am sorry. I knew this was going to be too small for me. Let me know if it happens again.”

I pull on the thin fabric to adjust it against my ass only for it to dive right back into my ass crack. He didn’t remind me again.

A dog toy fell out of the pool and I was trying to reach it. It was in this weird spot, and I strained to reach it. My ass is quite literally wiggling out in the open as I’m bent over the pool.

Mike: “Here let me help you.”

Me: “No. I got it! I’m a big girl. You just stand there and watch.”

And boy did he watch. It must have been a wonderful view. After I got the toy, our conversation was pretty normal. At least normal in terms of speaking to Mike.

Mike: “Hey, do you have a boyfriend?”

Me: “No boyfriend.”

Mike: “Oh. Then do you have a girlfriend?”

Me: “Haha. No girlfriend either. I’m not bi or a lesbian, but thank you for not assuming I guess. Why do you ask? Do you have a boyfriend or girlfriend?”

Mike: “No. No one likes me and I don’t have time. I don’t have any friends. I… I want to explore things with a friend, but I don’t have any.”

I started to frown. Mike has always been an outcast that I and the other popular kids in high school always protected. It always pissed me the fuck off how rude people were to him. Making friends has never been easy for him, so he decided to just shut everyone out.

Me: “Well Mike. I’m sorry. That sounds like it sucks and your feelings are totally valid. But you can’t shut out people. Yeah high school sucked, but you got to leave room for college to be different. There are people out there who would love to hang out with you and date you. And you’ll always have me as a friend, ok? :)”

I swam over to him and gave him a big hug with my chest pressed up against him. He smiled at me.

Mike: “Thanks. I didn’t really see it like that. I guess I gotta try harder. Always knew how to make me feel better. Let’s start heading out so we can watch Star Wars.”

Yay! He was back! And I could finally get to see Star Wars. I got out and started drying off when he asked me a question.

Mike: “What are your thoughts on nudity? Do you think it’s weird?”

Now, for anybody else asking this question, it would immediately be surprising and weird. However, Mike has always been the kind of person to ask sexually explicit and invasive questions without seeing any problem with it. It was always odd, but my classmates and I got used to it.

Me: “Not really. I walk around naked or half naked all the time in my dorm or at home since it’s always just been women. Some girls are weird about it, but not me. I mean we all have vaginas and boobs, so it makes no difference to me. I don’t really mind guys seeing me in my bra either because it’s the exact same thing in my mind as me in a bikini (lol what I’m doing now). It’s just waterproof lingerie haha. Does that answer your question?”

Mike: “Yeah it does…..Does that mean you are ok with walking around my house naked? Neither of my parents are home. I wouldn’t mind.”

Of course he wouldn’t mind. I giggled and politely told him no. It was pretty bold of him, but I didn’t think much of it.

He then offered to help me take off my “bikini” top. He gave me a towel and told me to wrap it around myself. He proceeded to unhook my bra. I was surprised but then he told me it was to dry it on the hang line (it dried so quickly and I didn’t have to go home with wet clothes: genius idea). I removed my thong under the towel and hung it up. As I was hanging it up, I started to blush as I looked at how soaked in my juices they were. I liked this more than I thought.

I wanted to take a shower so I asked for some lotion. He gave it to me and I started reading the ingredients in the hallway to make sure I wasn’t allergic to anything in it (I have a lot of allergies). As I was doing that, my towel was slowly drifting downwards and you could see my nipples peeking out very clearly. I didn’t attempt to fix it. I wanted to see how far I could push my comfort zone.

Mike: “Um… your nipples are showing.”

Me: “Oh they are? Ah that’s fine.”

Mike: “Well in that case, I can take your towel.”

Ok maybe not THAT far outside my comfort zone.

Me: “You’re so silly. That would leave me naked Mike. That defeats the purpose of a towel. I’m fine.”

30 seconds later…..

Mike: “Are you sure you still want your towel?”

This boy was persistent.

Me: “Yes I’m still sure.”

He must have been so confused with all the mixed signals I was giving him. Honestly, I was confused too. I didn’t like him but I had a desire to entice him, make him desire me.

I started thinking to myself about more ways that I could torture this sweet innocent boy and an idea sparked up. I realized that we were in the pool for so long that my advising phone call was about to happen soon. So I used this opportunity to just start freaking out about this really important meeting to him and told him I had to hurry. He was adjusting the water and when it got hot I just ripped off my towel and dashed in the shower. I guess I didn’t mind him seeing me naked as much as I thought.

Mike: “Umm… Do you need help?”

Me: “All good in here. Thanks!”

Mike: “Ok… Well I’m going to change.”

I love taking a shower. The feel of the warm water touching my skin as the water droplets caress me. It just makes me involuntarily sigh and moan with happiness. Naturally, I was not being quiet.

Mike: “Are you ok? Do you need anything?”

Sweet Mike. Maybe he could help me.

Me: “……Actually Mike yeah. My sister or roommate usually washes my back for me (complete BS). Can you wash it for me?”

Mike: “Sure! How do you want me to do it?”

Me: “Just squirt the soap in your hand and rub it all over evenly.”

Now, my face is to the wall. The bathroom is really steamy and I don’t have my glasses, so everything is blurry. Next thing I know, Mike is behind me INSIDE the shower NAKED. I tense up and freeze. I don’t dare turn around. This is not what I meant at all, but didn’t I push this? Was this a bad idea? He presses his hands on me lightly and I feel my body relax. I remind myself that this is Mike. He won’t hurt me. He’s always protected me. He’s just doing what I told him…kind of. Why is my pussy getting wet in this situation? Probably because I’ve never been this close to anyone naked before in my life. It felt….nice.

Me: “Make sure you wash it well ok?” I try my best to say in as regular a voice as possible.

Mike has really strong, big hands. It felt good as he massaged the soap into my back and shoulders while caressing the outline of my body. He rests his hands on my waist. I wonder what other things they could do….

Mike: Can I…. go lower?”

He’s touching me and it feels so warm. A mans touch is so comforting.

Me: “Hmmm. Yes you can. You’re doing a great job.”

He started to rub just above my ass, and I could have just melted. I’m trying to stifle a moan. After about 2 minutes, he’s done. He finished after that, got out, and told me he’d be in his room.

I got out of the shower shortly afterwards, and looked at the clock. I still had some time. I position the towel so that it’s only covering the front of me.

Me: “Mike. Can you come put lotion on my back?”

He comes back with a towel around his waist. He starts to rub my back while descending down to my ass cheeks. He lightly grabs them as he massages the lotion in. I can feel him breathing heavy. I realize I’m the one doing this to him. I am desirable. I don’t even try to hide how much I like it.

Mike: “You took good care of your body even after track. It’s all soft and firm. It looks nice.”

I smiled and thanked him when he walked out. I had my advising phone call and changed. I was wearing shorts that were basically underwear and a top with no bra because I forgot one (bikini bra was the only one I had). When I left, Mike’s door was halfway open and I saw him naked. He didn’t see me, but I stood frozen. Mike was the first cock I ever saw in real life. It wasn’t very big, but his balls were huge and he was hard. I didn’t know how to feel, so I just sprinted down the stairs and waited for him to come down.

We didn’t have time for Star Wars:( so we just talked. I didn’t have time to do my morning yoga, so I asked him if I could do it while we talked and he said sure. Downward dog. Cat-Cow. Chatarunga push up. Happy baby. Shoulder stand. Puppy dog. Did I mention that I was in a braless shirt and booty shorts? I eventually finished and me and Mike started talking again.

Mike: “Are you a virgin?”

Me: “Why yes I am.”

Mike: “Why? Are you waiting for marriage since you’re Catholic?”

Me: “Oh heck no. I’m just waiting for the right guy. I don’t need to be married or in love with the guy. I just want it to be with someone who cares about my wellbeing but will also make me feel good. Are you a virgin?”

Mike: “Kind of. I’m surprised that you’re not waiting till marriage or love. You’ve always seemed like the type.”

Me: “Well, that may have been true in high school, but I’ve changed. There’s a lot you don’t know about me. You’d be surprised.”

I had to go volunteer at the Boys & Girls Club, so we got in his car for him to drop me off since it was really close. About two minutes away while we were jamming to musicals, my outfit of choice dawned on me.

Me: “Oh no! I cannot show up there in this outfit. I will be eaten alive by my supervisor. I need to change right now.”

I started to remove my clothes.

Mike: “Wait! You can’t just change in the car! People will see you! **I** will see you!

Me: “Who cares? It’s just strangers who I’ll never see again and we’re friends.”

I proceeded to put on a bra while changing my pants and shirt. Mike’s protests stopped.

We got to the club. I turn towards him.

Me: “Thank you so much Mike for a great day. I always enjoy spending time with you, and I got so many new songs. Let me know if you need anything before I leave town okay?”

Mike: “Ok. Thank you for spending time with me today. You’re fun to hang out with. And thanks for all the advice.”

I hopped out of the car and waved as he drove off. I still couldn’t believe it. I was a tease! My friends were right! A couple hours later, I get a text from Mike. We start talking and it leads to him telling me about his sexual awakening as a bisexual male and his first blowjob and rimjob. He tells me he wants to give pleasure to a friend like one did to him. He then asks if he can have sex with me! Always straight to the point with him lol. I told him I wasn’t ready, and I truly wasn’t.

Mike was really important to me because he was the first guy to make me realize that my body could be desired. He was the first man to open my eyes to a whole new set of possibilities for myself. I’ve come such a long way since last year, and I owe it to him.

Now, I have it set in my mind that once I lose my virginity, if Mike is still a virgin when I see him again, I am going to fuck the life out of him since he’s such a great guy and would be caring. I can’t stay a tease forever. After all, what are friends for?

Source: reddit.com/r/gonewildstories/comments/ft9fg7/teasing_my_old_high_school_friend_fm