bigmuthac
Member
Posts: 27
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This is the story of my first gf and younghood sweetheart. My name is David. I’m 5’6’’, medium build, and fairly decent looking. At the time of these events I was a few inches shorter and kind of scrawny. Jess is a redheaded, green eyed girl. She has a few freckles and, in my mind, the most beautiful girl I knew. Josh, who will be later introduced, is a dark-complected Hispanic. He has dark eyes and was built lean but muscular.
Chapter 1:
Jess and I first met in 2nd grade; both of us were kind of the nerdy kids in class and didn’t really connect with our classmates. So we instantaneously became best friends and were connected at the hip all throughout school. Our friendship started out innocently enough, we did everything young kids do like play doctor, though she was always the doctor, and played about. At 10 we had our first real kiss and became bf/gf. Nothing really happened being as we were both fairly innocent and Jess was extremely self-conscious. When we were both 11, Jess began to fill out. What was once an ugly duckling became a fairly womanly tween. She didn’t grow much taller and cut off around 5’3’’ but her breasts got really huge (DD’s) and her body filled out into an hourglass. To say the least, she wasn’t pleased. She became ever more self-conscious and began wearing loose fitting clothes to hide every part of her body; hating the initial attention she was getting from the other boys.
But, while she was seemingly growing up, I stayed very much a boy. It was around then that my classmates started talking more and more about sex. So, over the next two years, I made it my goal to lose my virginity.
In middle school, Jess and I labeled ourselves as outcasts. In the small, religious town we came from, that meant going out of our way to find trouble. While still severely nerdy, we did befriend a guy named Josh who had dropped out of university the year prior. He was 21 and able to buy us ***** which we richly enjoyed. The three of us hung out all the time after school and, to say the least, we worshipped him like an older brother. Josh even took me under his wing; he taught me all about sex and bought me dirty magazines. He knew I was trying to get into Jess’ pants and gave me all his secrets to get laid. Unfortunately, they never worked and I became increasingly frustrated. I hadn’t even seen Jess’ bare breasts yet after nearly 7 years. At 14 I finally was having my fill, the guys at school would tease me about being a virgin and I was going crazy. I was tired of just making out. Josh told me that if she wasn’t putting out that I should find another girl and, soon after, I told Jess that we were done.
She was devastated and we didn’t talk for weeks. Josh and I continued to hand out and he coached me on picking up girls. But, even at 14, I still hadn’t fully bloomed. I was a scrawny, nearly hairless kid and all the girls at school new that. After a few weeks of failure and silence, I called Jess to see if she was okay. We decided, even though she was still hurt, that we should still be friends. She even told me she had found a new bf. I was extremely shocked and rather jealous but decided to not let it show; instead playing suave and talking about imaginary girls I met at another school. We ended the phone call friendly enough and promised to get together the next day at Josh’s apartment.
At that time, primarily because Jess matured before I did, she and I didn’t have any classes together. While she was in the gifted classes, I was stuck in the lower level normal classes. She texted me before the last period telling me that she was bailing out of class and to meet me outside. Unluckily enough, I was caught by my teacher and had to stay in for the last hour. I told her I was sorry and that I’d meet her up at Josh’s after school.
When I got there I knocked on his door and he called me to come in. To my surprise and horror I found Jess sitting on Josh’s lap while watching TV on his love seat. She turned to me and said hi while taking a swig of beer. I, in a stutter, asked what was going on. Josh said that they had gotten together a few days after our breakup. He asked if it was cool and that Jess had told him we had decided on still being friends and that he figured that since I had apparently hooked up with another girl, it was all good. Not wanting to seem like a loser, I shrugged it off and lied again about my imaginary girl. I sat down on the couch next to him and we chatted awkwardly about the day and how I’d gotten caught by my teacher before escaping.
I noticed Jess was wearing a short skirt, something she never would have worn, and a wife beater. I asked where she got the clothes and she said Josh had bought the skirt for her and that the shirt was his. “Yea”, Josh said, “I prefer her in these than her old clothes, it gives more access”. As he said this he was fiddling with the skirt and rubbed her inner thighs. Jess seemed to squirm at the touch and closed her eyes for a second. They then asked me how I have progressed with my “girl” and I filled them with macho lies. Out of sheer horror, I asked how they had gotten together without even thinking.
Apparently a few days after our breakup, Jess was hanging out by a local river. Josh found her crying and tried to console her. He told her not to be upset and that this was all a part of growing up. They began to walk and talk before getting a little flirty. Josh jokingly pushed her and she inadvertently landed in the water. Being a cold day, she needed a change of clothes. Her jeans were soaked and she could barely walk so Josh gave her his shirt. Josh, being 6’2’’ had a big enough shirt to cover her head to toe which allowed her to take off her bottoms. Jess got really red faced at this point and told me that, in order to not get his shirt wet and under his wish to not have to throw it in the dryer, he made her undress completely first before putting on the shirt. I, scared out of my mind, asked how she was able to do that without him seeing. He had teased her for being a prude and commented that he had seen many girls naked before (he was considered a player) so her nudity was completely normal to him.
I was completely shocked; I had never seen Jess naked yet Josh, who wasn’t even her bf yet, got to see the goods. She then proceeded to take off all her clothes, to Josh’s taunting. When completely in the buff, Josh teased her further but not giving up the shirt. “I couldn’t believe she was a natural redhead. I have to admit, that was a first for me. I couldn’t help but need to get a closer look!” Jess pushed him a little on the couch teasingly before continuing, “yea, right! Then why’d you grab my boobs too? You must’ve seen hundreds of those by now!” I muttered “too?” and jess must’ve heard me because she replied, “He wanted to feel what my pubic hair felt and, instead of stopping there, he tried to put a finger in me! I stopped him, though, and managed to get the shirt on.”
“What happened next?”
“We walked back here and he put my clothes in the dryer and… yea…”
“Yea?”
Fidgeting a little as Josh continued to massage her thighs, “Like a gentleman he offered me a hot shower to warm up. Not like a gentleman, he joined me.”
“I couldn’t help myself”, Josh inserted, “plus, being so young, I wasn’t sure she was able to wash herself”.
“I’m 14! I don’t need someone 10 years older than me giving me a scrub down!”
“You did enjoy it though”, he slyly replied, giving a sensual kiss on the neck.
“Yea, I did,” she sighed. “Do you mind we’re talking about this? I mean, we’ve shared everything for years…”
“No, no, I don’t mind”, I squeaked, “I already told you about my girl”.
She seemed to get a little excited about this and sat up with her legs across one of Josh’s legs. I could see that the skirt wasn’t covering underneath her and laid out just enough to hide herself as she moved closer to me. My stomach had a lump realizing that the only thing between her and Josh’s leg was her panties.
“I know it’s kind of weird since we used to date and you were the only other guy I’ve kissed but I always hoped we’d share our sexual firsts with one another. And, while I thought those would be with you, I’d still like to share them because you matter so much to me. We’re family the three of us and should be open.”
I halfheartedly agreed and allowed her to proceed. Josh now had a huge grin as she spoke, “Well, you already know that I’ve seen your penis and that I always liked it and thought it was really cute”. My heart sank. “But, honestly, it’s a lot different with someone older. I was so scared when he got into the shower and couldn’t look at it for the longest time”.
“I didn’t mind too much”, Josh interrupted, “It gave me a chance to scrub her down. She didn’t put up too much of a fight. I gotta say, I haven’t felt up a girl as young as you guys for a long assed time. I forgot how tight teen pussy was!”
“God, you’re such a pedo!” Jess teased, “He insisted that we wash each other down or he’d put a finger in me. So I just gave in and he scrubbed me down to a really unnecessary length and I scrubbed him. While I was washing his… down there… he pulled me in and we kissed.”
Jess was looking down at the floor blushing as Josh took charge again with the conversation. “I hope you don’t mind, bro. I had to step in after you guys broke up. You’ve got to bend the tree while it’s young, like I told you. Anyway, she stopped it after a while and got out before any more could occur. After that we just hung out while her clothes dried.”
“Yea, except you kept pawing at me and even after my clothes dried, you didn’t let me put them back on. He now says if I want to hang out here I can’t be dressed. It’s only because of you that he let me put on a t-shirt and skirt, thank God!”
“Bullcuckolds brownie, she enjoys prancing around here naked. I think she thinks it makes her grown up. Hell, I have a hard time keeping them on her!”
“Oh, shut up!” Jess exclaimed before falling back against his chest and giving him a long lingering kiss. I felt my stomach turn when their lips met, staring in horror as my first and only kissed a guy 10 years our superior. “So that’s how we got together. And I kinda want to watch tv, were missing good tv.”
With that we proceeded to watch some show I can’t recall and take a few beers. Jess served Josh every time he finished on off and would give her a slap on the ass as she got up. After an hour or so they got pretty connected in their cuddling and Josh began whispering in her ear.
Jess turned to me and asked if I felt uncomfortable with their pda and I told them I was cool with whatever they were doing since she and I did a lot of making out with him around. That followed with some heavy regret as they got into a pretty heavy makeout session. Jess sort of rapped her body around him as he rubbed her backside and squeezed her ass. Once in a while he’d pull up her skirt a bit and she’d half to pull it back down telling him no. This lasted until both of us needed to head home.
When it was time to go Jess got up and asked Josh where her clothes were. He replied, “in the bedroom” and proceeded to follow her in. I heard a bit of scuffling and giggling in the other room, there was a thump as if someone had fallen on the bed and a squeal before Jess yelling at him to, “give it back”. Josh came out of the room holding a pair of purple panties and threw them on top of his bookshelf.
“I’m keeping these”, he said as Jess poked her head out the door.
“I need them to get home! It tingles when I don’t have them on…”
“But I told you no more panties! You can wear your usual outfits when you have to go home but I won’t have you wearing these. No panties inside or outside my apartment. I let you get partially dressed because David was coming over but I can’t accept this.”
“You weren’t wearing panties?” I asked realizing that she had been sitting bare on Josh’s lap the entire time.
Jess blushed, “No, I wasn’t. I had to argue enough to get him to wear anything while you were here. Look, I’ll be right out. Let me put on my jeans.”
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bigmuthac
Member
Posts: 27
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Chapter 3:
“Hey bestie”, I heard over the phone, “you get home safe?”
“Yea, mom had dinner ready but I told her that we ate already.”
“Oh, so you told her we made up?”
“That’s what she assumed anyway.”
“Awesome! I’m so relieved. Josh and I don’t have to worry so much anymore. You really are great, David.”
“So what do you want to talk about?”
“I was hoping to catch up some more. It was an entire month that we didn’t talk. Did anything interesting happen to you?”
While I really didn’t want to talk at all, I still gave her an account of my classes, the girls, and Josh trying to give me pointers. She laughed about Josh, saying how he’s such a player in his mind but really is just a cuddly teddy bear inside. Unfortunately there wasn’t much to say on my part so I turned the topic to her month.
“After what I’ve already told you we’ve mostly been hanging out in his apartment. I just come over, strip down, and either help to tasks around the apartment or fool around. Actually, it was the weekend after we got together that he took me to the mall to get some new clothes. He chose everything, of course, and had me show it off for him. It was kind of exciting because he had me try on these really skimpy skirts without any panties. He even inspected to make sure that I wasn’t wearing any by making me bend over when nobody was looking. I kept a pair on when we changed stores so he could reach in while we were looking through the racks. I felt really naughty having him finger me I the stores.”
At this point, out of much sexual frustration, I gave in and began to massage myself. I was as hard as I’d ever been listening to her talk and giggle about being worryed in the mall, something that she wouldn’t have done in a million years with me. To be honest, I was curious and new very little about sex and neither did she. Looking back, I can see that we were still exploring our sexuality together even though it was her sharing the experience with me. A part of me was, in fact, happy to know she was happy and excited. Hell, I was excited to hear more. In my mind, I was still technically her bf to everybody else, albeit a pretend one. I encouraged her to continue.
“I think you’re starting to enjoy this!” she teased, “well, after some shopping and parading around for him, we went and saw a movie. I know we kissed a little in the theater but I actually gave him a hand job! I was convinced someone would see us which made me really wet and I came like 5 times. Josh had to kiss me real hard to keep me from making too much noise. Though, he didn’t get to cum in the theater so he had me go down on him in his car. It was really funny because his windows got all foggy which gave us enough privacy to get in the back seat so we could 69. That was the first time he tasted me. He says I taste like honey but I don’t believe him because he had me suck his finger and didn’t taste a thing. But it was still really nice especially since we came at the same time. All I remember for the last bit was the slurping sounds of us sucking each other. The closer I came to cumming, the more I focused on swallowing his cock until we both had this huge spasm and held on for dear life not wanting my mouth to leave his pulsating head. Fuck, that was fucking fun!”
I was really surprised, and horny, hearing that they were doing so much. I interrupted her for a minute asking if anyone’s caught her in her new skirts.
“Kind of, Josh likes showing me off, especially in front of his college buddies. We’ve hung out with them a couple times now. The first time was the day after he got me the new clothes. My parents left town that weekend so I didn’t need to worry about getting home early. We drove into the city and met up with his friends. They were nice enough and kind of stayed away for the most part. I think they were surprised by me and my outfit. I was wearing this black v-collar shirt with no bra so my boobs kind of hung out. They asked me how old I was and I said 14 which they made fun of Josh for. They said he was robbing the cradle. That annoyed me a bit and I tried to tell them off saying babies don’t have DD’s. They continued joking, saying I was obviously stuffing my bra, even though I wasn’t wearing one, so I flashed them! You should have seen the dumb looks on their faces. Josh just smiled as they ended up congratulating him for getting such a fine teen.
“The next couple hours we walked around town, Josh kept on dropping things on the ground and asking me to pick them up. At first I said no but after a while I got tired of it and decided that it was easier just to bend over and show my ass. We eventually got to a park and sat around the grass. Trying to get even with Josh, I sat right next to him and opened my legs for his friends. They all just stared and couldn’t talk so I asked them if they were enjoying my tight teen pussy. I figured Josh would’ve stopped it there but he didn’t so I reached down and started to play with myself. I got really wet knowing these guys were watching me. Then I asked them how old they were while I began inserting a finger. All of them were around Josh’s age except a guy named Chad who was in his thirties. Knowing I was fingering myself in front of a guy that old pushed me over the edge and I came right in front of them!
“God, I came so fucking hard! I loved showing myself off to them; they’re eyes on my most delicate parts…” Jess began to moan a little as I asked her what happened next. I was stroking myself and was harder than I had ever gotten.
Jess laughed, “Josh punished me… Well, actually, we went to his apartment and made me take off all my clothes in front of the guys… On the way back he told his friends that they could look at me all they wanted and to enjoy my company as they pleased. Of course, if they touched me down there, I’m sure Josh would ******* them but so far he’s been cool with them giving my tits a squeeze and slapping my ass. I can tell they really enjoy giving me hugs goodbye cuz’ their hands always cup a feel of my butt. Not that it’s bad, I really like the attention.
“Anyway, I had to do a little strip show for them too which included me in the middle of his living room to a ‘v’ for victory. That’s when a girl lays on the floor and tries to get her legs up to her head. I actually got it up really high until my butt was in the air. They really cheered when I did that so I spread my pussy lips at the same time so they could get an eye full. One of them called it a ‘w’ which made me laugh. So, after that I just hung around naked and showed off some more. When we’d be sitting around I’d gently stroke myself and stick a finger inside. By the end of the night they all had tents in their pants. I really loved teasing them and shaking mah bootie at them, poking it out so they could see my holes.”
“You don’t mind being nude around a bunch of strangers? I mean, you had clothes on when I saw you earlier.”
“Well, like I said, it’s different with you. We have a history that means something, these guys just see me as a piece of ass; which is nice because I feel like the center of attention for once. They’re like pals who I can be nude around without worrying about their feelings.”
“I guess I understand… So anything else happen?”
“Not really, I’ve just been getting used to being naked around guys and practicing my cock sucking s*******s on Josh. It’s been a huge adjustment, no pun intended, but he’s been a really good boyfriend. I don’t think anyone would’ve been better fit to get me out of my shell and teach me about all this. He’s just so grown up and knowledgeable and mature and sexy. I get tingly whenever I think about him and his…”
She was panting again before telling me it was time to go to bed. I said sure and we said our quick goodbyes. I laid in bed for the entire night thinking about what she had told me, imagining her beautiful lips against Josh’s, her tongue flicking across his cock, and sharing the body that I never had. Eventually I fell arelax but only to be quickly awoken by my alarm. It was time to get up for school.
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bigmuthac
Member
Posts: 27
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Chapter 4:
Getting up, while difficult, was at the very least heightened with the curiosity as to what could possibly happen next. I hurriedly got ready, ate breakfast, and started my walk to school. It wasn’t long before I heard a cry of “hey, honey” and Jess ran up behind me, giving me a kiss on the cheek and holding my hand. Obviously seeing my startled look, she nodded her head to some of the other kids also walking to school. To try to clear that up I moved in to give her a kiss and she backed off before reminding me that this was all for show and her lips were now Josh’s.
Holding her hand made my heart beat right out of my chest. It gave me an unfounded hope that what we had was real and that she’d come right back to me. Unfortunately my newfound glory disappeared when she asked if she could run into the bushes to change. When she came out she was once again in a short little skirt without, as she reminded me, any panties and a lower cut tank top. While I knew who it really was for, some of the guys gave me proud looks for the slutty outfit, giving me some additional false confidence.
We spent lunch together pretending to be back together and behaving like any other couple would, minus any kissing or heavy petting. Getting to touch her hand, while not much, was still the world to me. And even though we were pretending, I couldn’t help but begin to believe the lie. Before separating our ways in the school hallway I asked her what she was doing after school. She winked and told me she was going to “practice,” leaving me to think about her going down on Josh as I went to class.
I had figured that I needed to walk her over to Josh’s since we had to keep up our presence as a couple but didn’t find her in the parking lot after school. Instead I took a lonely walk home and went into my room to play video games.
After about an hour I got up the gumption to pick up the phone and give her a call. I figured I’d make sure she was okay and get the details about Saturday which was the very next day.
She answered with a muffled, barely audible hello.
“Hello? Jess? You there?”
There was a small popping sound before Jess responded with “hey bestie, what’s going on?”
I told her that I was playing video games and checking up to see if she was okay. As I was saying this I heard odd muffled sounds before hearing another louder pop and her replying that Josh had picked her up in his truck and that she was currently at his apartment before taking a breath and making a light slurp sound.
With this I asked her what she was doing.
A smacking sound followed by a little giggle, “practicing”.
“Practicing?” I blurted, dumbstruck.
“Yea, silly, I told you I was practicing today! Josh wants me to master my deep throating s*******s, it takes a lot of practice.”
“Oh…” I fell into shocked silence while the slippery sucking sounds continued on the other end.
Another pop and gasp of air rang out at the other end. “Yea, he didn't let me stop even when my mom called. I had to tell her I was eating noodles, I figure it sounds about the same. So is there anything else you called for?”
The sounds of her mouth got even louder; she was panting and gagging on the other end, as I asked her about the movie plans.
“Oh, yea, Josh can tell you about it. Hold on.”
I heard her tell Josh what I was calling for as she passed it to him.
“Hey, bro, sorry about the interference. Uhm, the movie starts around 1 so if you could bring Jess to the theatre at 12 that would be great. I’ll be paying, of course, and afterwards we’ll stop by a store to buy some beer and head over to my place. Jess said you wouldn’t mind waiting around while we consummated the relationship. So after that you can take her home. I really owe you one, dude“.
I was in a complete daze as I replied, everything was hitting me. All of this was becoming a reality and I felt sick to my stomach. “It’s cool; you’re already paying for the beer and everything.”
“You don’t even know. I owe you beer for life. Jess is such a sexy little minx, I’m in fucking heaven. Anyway, she’s getting really good at this so we gotta go. See you tomorrow.”
He hung up the phone before I could speak. That night I lay shivering in bed until sunrise. I watched television until 11 when I figured I’d go pick up Jess. With little hope I left the house and entered the light of day.
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