So for a little back story, my name is Jacob but I always go by Jake and I was always kind of shy and quiet growing up and have stayed that way even into adult hood. I never really had any fetishes or anything that I knew of when I was younger, that is until I met my girlfriend. I'm 5'9" about 150 lbs and have blue eyes with curly blonde hair. I've also always been a little self conscious about my penis. I'm about 4.5 inches hard but when I'm soft it's extremely small, maybe 2 inches on a good day and I have a lot of foreskin that still hangs off even when I'm hard. I never even wanted to have sex in my younger years because I was afraid of a girl thinking it was too small and laughing at me and just leaving.
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But then I met my girlfriend, Ashley, I was 21 and she was 24 when we met which was about 3 years ago now. She came up to me and asked for my number cuz she thought I was cute, so I of course gave her my number. She is about 5'8" and long brown hair with a cute innocent looking face and a great body, of course I'd give her my number. When we first started dating there was a lot of making out and me fingering her and eating her out but after 2 months together she had still never seen me naked. So she asked about it one day,
"Why do you never let me see you naked? You've never even me give you a hand job before."
"I don't know, I guess I just don't want you to think that I'm not enough down there or something…"
"Baby, I promise I won't think that. Did one of your past girlfriends say that?"
I didn't say anything as I just stared at her, as she didn't know that I was a virgin until just this moment.
"Oh.. wait.. other girls have seen it haven't they?"
"I guess I should've told you sooner…"
"Oh my god! Baby! You're a virgin!?!"
"Yeah…" I said while looking at the ground.
"Why didn't you tell me!? That makes you even better! I get to be your first! Oh my god, that makes me so happy baby!"
"Really???" I asked, knowing that she's been with multiple other guys.
"Yes baby, I'm seriously so excited to be your first!"
So we made plans to have a date night at her house that same night and I got all dressed up and went over to her place. We had a really nice dinner together then we went to the living room to watch a movie. Some marvel movie I think. About 15 minutes into the movie she starts making out with me and I get super nervous knowing that she's going to see me naked tonight. My blood is rushing as she puts her on my crotch to start feeling my dick but when I'm sitting it kind of gets sucked in, so she can't feel it and instead she just shoves her down my pants. I feel her go to grab my dick but she kind of opens her eyes in confusion when she can only get two fingers on it. She pushed me back and climbs on top of me and when I lay down my penis comes up a little more and she can get her whole hand wrapped around it as I'm now rock hard. But she still looks confused.
"Are you still soft baby?" She asks.
"No…"
"Oh ok, just making sure is all." She says in a reassuring tone.
She gets up and pulls my pants down and finally looks at my penis for the first time. It's standing straight up, pointing to the ceiling with my foreskin hanging off the tip and she just looks at me.
"I'm sorry, I told you it wasn't very big.." I said to her.
"No no baby! It's so cute! I love it. You don't have anything to worry about. I love it, I promise!" She was so reassuring, it was almost confusing. She then takes her clothes off, "Well at least we won't need a condom, since I'm on the pill and I definitely know you don't have any STD's!" She says with a little chuckle.
She goes to climb on top of me and I'm trying to put it inside but I'm having a little trouble, so she grabs it with two fingers and guides it inside of her. The very second she sits completely down on it I feel like I'm going to explode. She starts to grind, as she can't really bounce without it falling out and I immediately explode inside of her.. I begin moaning so loud, I don't even know where it came from. I just couldn't hold it back. She looks down at me and says,
"Aww baby, that was so cute. You moaned so much, I've never heard a guy moan like that before."
"Oh umm.. I'm sorry.. I didn't mean to."
"No, I loved it!"
"Oh ok, and I'm sorry that was so quick.. it just felt a lot better than I thought it would.." I said while just looking down as she was still sat on me with my penis inside of her.
"No no! It's ok! I promise! I knew it would probably be a little fast since it's your first time. I'm sure you'll get better the more we do." She says while giving me a silly wink. "But umm.. do you think you could help me to finish off since I'm still, you know.. pretty horny." She says with a laugh.
"Of course! I'm sorry, I didn't even think about it."
"It's ok baby, let me just lay down."
She goes to lean back and my penis comes out of her and is still standing straight up but now completely soft and she is covering her pussy as she lays down on her back and then she spreads her legs open and holds her knees up. "Come eat me out baby."
I'm not going to lie, I was a little confused as I just came in her and thought it would be kind of gross. But I honestly just didn't know any better. This was my very first sexual experience of any kind, outside of just fingering her and eating her out. So I thought, ok maybe this is just something people do after sex. I go to kneel between her legs and I begin eating your pussy. Surprisingly it tastes just it always does.
"Does Mommy's pussy taste good baby?"
"Mmmhhhmmm" I mumble while still licking her warm pussy. That was the first time she's ever called herself that. It was a little weird but not really that crazy, considering girls call guys Daddy all the time, right? I look up while my tongue is deep inside her to look her in the eyes and she looks down at me then grabs my head and pulls me tight into her pussy. I then see her flex her stomach and all the sudden all of my cum that was inside of her fills my mouth. It just flowed in and I couldn't move to spit it out.
"Swallow it all baby, I want you to taste all of our juices together." She says.
I quickly swallow my cum so that I can at least get it out of my mouth. I got back to licking her pussy as she is still holding my head tight against her and she then begins grinding her pussy against my face. Rubbing herself all over my face from my forehead to my mouth, over and over and over. Until finally she has a massive screaming orgasm on my face. Once she cums she finally lets go of my head.
"That was amazing baby, you did such a good job for me." She says.
The words actually filled me with so much joy, "Thank you baby, I just wanted to make you feel good!"
"Oh I know, don't worry. I'll make sure you always make me feel good." She says with a little chuckle and a wink. She then looks down at my penis that's now even smaller than what she seen before. "See, you don't have to be big to make me orgasm. I like your cute little guy baby."
That was like a dagger to my confidence… But she was right. As long as she's happy why should I care?
"I bet you could fit that in my panties even! Actually! Why don't you just try them on! Come on, it'll be funny!" She's now sitting up and grabs her g-string she just had on and hands it to me. "Here! Let's see!"
"Ummm I don't wanna put on girls underwear.. that kinda weird.." I say hesitantly.
"Baby it's fine! It's like anyone else is gonna see!" She encourages.
"Ok fine, but you better not tell anyone." I take the pink size small Victoria's Secret g-string and slide it up my legs. Oh my god.. she was right.. my knew I was small, but just putting on this tiny little g-string it's like it just disappeared.
"Awww!!! You look so cute baby!! Look at that booty!! Keep them on!!"
"Babe…"
"Please please please!!! Just for tonight! For me!! It's not like we're going anywhere anyway. Plus, I'll make it worth your while in the morning." She again winks at me.
"Ugh.. fine.. but just for tonight."
"Yay!!" She bounces with a little clap.
I go to lay down on the couch so we can finish the movie and cuddle but she goes into her room and comes back out in a full set of pj's with long pants and long sleeves.
"Hey! I thought we were gonna stay naked!" I begin to argue.
"I know baby, I just get so cold. You stay like that though so I can see that cute little booty! Here, come cuddle up on me and I'll keep you warm."
I'm now even more embarrassed than I already was. Completely naked in a g-string while she's fully clothed.. she lays back on the couch and opens her legs and arms for me to lay on her. I go to lay on her she rests my head on her perfect little boobs and as she begins rubbing my back with one hand and she puts the other hand on my butt and pulls on the g-string a little bit while giggling. We fell asleep right there on the couch.
I definitely was not prepared for what the coming weeks, months, and years had in store for me…
(Come back for part 2 when the cucking begins.)
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