Ugly Ducklings Pt. 01

Ugly Ducklings

Pt. 1

"So how was your first year of college?" I asked River.

"Oh, fine I guess. How about you?" River frowned and I could tell that he was withholding a real answer.

"The actual classes were good, but everything else was like a repeat high school. I thought things might be different at college, but it was mostly the same."

"Still invisible Isabella?" River asked, cracking a slight grin. He knew I felt invisible sometimes and used to tease calling me "Invisi-bella" until I asked him to stop.

"Pretty much. What about you?"

"It was actually worse than high school. At least In high school I had my teammates and a few friends. College has been different. I had some trouble in the dorms, and I didn't connect with anyone. I joined some clubs and found a few guys to play pickup ball with, but it has been tough."

River was over 6 feet tall and skinny and awkward. His face was overly angular and masculine looking but it didn't fit his skinny body. His mom was proud that he had been varsity in football and basketball, but he was an average athlete and had no chance of playing in college. Like me, he was also a book nerd and was studying to be an engineer working with water. I was studying environmental sciences and economics, and we had some coursework in common. River had gotten top grades and earned a financial scholarship at a university on the other side of the state, so I hadn't seen him since spring break. We didn't have the money, and I didn't have the grades, so I was at the local state college and living at home.

"What happened in the dorms?"

"It's embarrassing."

"Come on River. Remember that time I bled through my white shorts at school. It can't have been worse than that?"

"It kinda was. There was this girl Kayla that lived downstairs from me that I met on the first day. She seemed friendly, but she also liked to tease me, especially about being shy. She was kind of mean about it, but I guess I liked the attention, and I thought she was cute. She had tiny boobs and always wore these tight shirts with no bra so that her nipples were always sticking out. I know I should be able to handle that and not objectify her, but I just found her confidence so attractive." River had this pleading tone in his voice willing me to understand.

"Anyways, one Saturday night, we were having this open house party between the halls, and she got high with a few guys on the balcony. When she came back in, she asked if I wanted to check out her room. When we got there, she closed the door and whispered in my ear that weed makes her horny. She then sat on the edge of her bed and without any prelude, she started opening my pants. I was super nervous and I was totally soft in her hand. She tried stroking it and I tried, but I was so nervous and, in my head, about whether it was ok to be with a girl when she was high that I just couldn't get it up. I am hard basically constantly, and I couldn't get it up for my crush who wanted me to fuck her. It was humiliating. She eventually got pissed and kicked me out of her room".

"Before the night was over, I heard the other girls giggling and looking at me differently. Word got around the halls fast and Kayla would make little snide comments or wave at me with a limp pinkie and stuff like that. It became a thing that she would get high and have sex with one of the guys on the floor. They started calling her the village bicycle."

"I don't know what that means?"

"It means everyone shares it and they have all had a ride." I frowned at this. It sounded degrading and judgie.

"They weren't being mean, she just liked sex and eventually they had all had sex with her multiple times. Everyone, but me. Somehow, I always heard about who she had fucked. The other girls tried to be nice, but they mostly ignored me. I guess the guys didn't respect me or were embarrassed for me. Nobody would look me in the eye so I stopped hanging around the dorm when I could avoid it. I wanted to transfer, but I have to put up with it and make this work."

"I am so sorry River. That girl sounds like a total bitch. I didn't get teased or anything but the guys I dated were total ass's and I also mostly struck out. Theres this one guy that I gave a few hand jobs."

River nodded listening patiently.

"There was this guy from one of my classes that was sort of cute and asked me out. We saw a movie and after, we started making out in his car. He went for my chest and I brushed him off. I guess he took that as a sign that I didn't want to be touched, so he took my hand a put it on his crotch. When I didn't pull away, he got his thing out and I just stroked him until he finished. That was only the 2nd dick I had ever touched. After that he would call me up randomly and we would watch a show or have some food and then he would just kind of get it out. I let that happen too many times before I told him to stop calling."

"It sounds like that guy is was a prick, but I can understand why he thought you didn't want to be touched."

"Just because I don't want my chest groped that means I am not interested?"

"Well yeah." River responded.

I sat glaring at him waiting for him to justify this male behavior.

"That's like the normal way." He tried to explain. "Girls won't tell a guy what they want or what's allowed, so a guy has to read the signs. It's like a custom for establishing consent without directly asking. If the kissing goes good, you touch her boobs. If that goes okay, you can go under her shirt. If she is still ok, you go over the pants and then inside them and then hopefully you take them off and you know. It all happens."

"But what if I want to skip the boob groping? I can't get any farther? I just wish these guys had the balls to try something beyond touching my boobs."

"Have you asked them?"

"No. Guys need to man up a bit and make a girl feel like they want her. They are supposed to try." I said exasperated.

"Come on Bella. With all the messages we get about consent, most guys are trying to get signs from girls that won't tell them what they want or if it is ok. The kind of guys that gets a 'no' response on your boobs and decides to aggressively go for your crotch should be a red flag."

"I just wish guys weren't such wusses. Geez, we have screwed you guys up, haven't we?"

"Yeah, I guess. I don't know. It's kind of late. I think I am going to head to my room."

I only realized as I was headed to my own room that what I had said about boys needing to 'man up' probably hit a little too close to home for River and I had hurt his feelings. Like every year, our families were together for a vacation. This year it was Miami. River was the only person I knew that was my age, so I hoped I would be able to make it up to him tomorrow.

---

As I walked down the hall, I thought back to that first penis I ever touched. It was Brad, the first chair trombone in the school band. I was 2nd chair flute. It was our summer band trip for the graduated seniors. We had travelled to a theme park in some big vans. In exchange for doing a 1-hour set each day of movie themes and other pop song medleys, we got to visit the park for 3 days. Most of us were 18 and the chaperones were chill. It was a lot of fun. I felt so lucky that mama had saved enough for me to go.

On the way home, Brad and I were sitting in the back row of the 12-passenger van. The van was stuffed with instruments so it was just the 2 of us on the bench seat. He and I had been flirting through the trip, but nothing really came together. As we endured the 4-hour drive home he crept closer to me until we were touching and I rested my head on his shoulder. I wanted him to kiss me, but our top halves were in plain sight and that would be so embarrassing.

I had a sweatshirt over my lap to keep my legs warm. I was surprised at first when he put his hand on my thigh lightly caressing my skin, but I liked it and opened my legs so that he could move higher. Soon he was touch me all the way up to the tops and starting to rub my pussy over my shorts. I did the same and soon I was rubbing his hard penis through his shorts.

He then whispered in me ear, "That's chafing, is it ok if I get it out?"

I was so nervous, but also curious and excited so I nodded yes. He soon had his shorts and underwear pulled down enough that his penis was out in the open. He wasn't circumcised and I hadn't seen many pictures of dicks like that, but I could see that the head was starting to emerge from the foreskin and the tip was shiny with some clear fluid. I wasn't sure what to do, so I did the obvious thing and started lightly stroking him the way I imagined guys did themselves. I tried to sit up and look normal as I jacked him off. He reached down and adjusted my grip and pace and just whispered, "Like that yeah."

The skin of his penis was surprisingly soft and pliable feeling like a loose jacket over a hard rod. I was surprised that it seemed smaller than I had expected, but I didn't really have any grounds for comparison. I tried to pay attention to every detail of the way the head gradually emerged as I rubbed the foreskin and felt the ridges in his hard shaft on the underside. Before I knew it, he grabbed my sweatshirt and came into it. I was taken by surprise as his dick pulsed in my hand as he shot into my sweatshirt.

I hadn't expected that it would smell, but the scent of his cum quickly filled the van and someone cracked a window. I heard a girl up front mutter, "Fucking seriously? In the van. SO gross."

I was so embarrassed, but Brad wiped himself off and tucked it away and I put my sweatshirt in my bag hoping to contain the smell. For the rest of the drive, we cuddled, but the moment passed. I thought we would hang out over the summer, but he never called. Fucking asshole. The same shit just keeps happening.

---

As I walked into the room I was sharing with my mom and little sister, Scout, they were getting ready for bed. She asked, "You are back early. How's River?"

"Sounds like he had a rough year at school."

"Becky alluded to that, but she doesn't know the details. What happened."

I didn't really want to break his confidence, but I didn't see the harm of giving her some high-level details. "He had a date with a girl from his dorm and it didn't go well. She told everyone about it, and he kinda got bullied. It sounds like it sucked."

"His mom figured it might be something like that. He is so shy. She tried, but she ended up with a mama's boy. Sounds like you guys talked about your dating lives. Did you guys... connect at all."

"It's not like mom. Can you imagine River trying anything!? He is kinda cute and tall, but he is so shy and awkward. Besides, I only attract creeps and neck beards. He wouldn't want me." I had gone through a series of phases in high school with goth and anime and hanging out with the video game guys, but I always felt like I was larping. Lately, I reverted to trying to figure out how to be a 'normal' girl. My mom was thrilled and trying to help, but it felt hopeless that I would meet someone that wasn't a jerk.

I was old enough to know that I was no prize. I have frizzy brown hair that was currently in a poorly chosen short cut which didn't fit my face. My face is fine, but plain and I usually don't do much for makeup. The doctor says my boobs are in the "normal range of variations" and mom showed me pictures from the internet of women with boobs like mine, but I am embarrassed about them. They are small and narrow and asymmetrical. The nipples are big and pointy. My areolas are puffy and the same color as my skin, and also freaking huge taking up almost half of each boob. They look nothing like the pretty girls I see basically everywhere. I generally hide them with padding and oversized shirts and sweaters. Then there is my butt. I love playing tennis, and I have strong legs, but they are too thick. My butt and hips are wider than my shoulders giving me a pear shape. I feel like my boobs are from a Picasso painting and my bottom half came from a completely different person and I was put together by accident.

"Becky and I thought that maybe you and River would fool around and learn from each other a bit.", my mom continued. "There's no harm in some innocent fun. That's why we have never fussed about you spending time together on these trips. River has always been a good friend for you and a nerdy boy like River would be thrilled to get some female attention. He is there for you if you are interested."

"Mom, you have seen my boobs and my body. Guys don't want this."

"Bullshit Bella. That is utter bullshit. You are smart and funny and have a good firm butt and a tiny waist, nice hips, and a cute face. Boys will like you for who you are AND how you look. You just don't do anything with your gifts. Boobs aren't everything Bella. You won't listen to me about your hair or makeup or clothes or anything, because you want to hide. Boys don't want invisible girls Bella. It's just how it works."

I just glared at her. Tears streaming down my face.

"Aren't you tired of this?" she asked. "Won't you let me help you?"

"Help how?" I sniffed. "You always pick tops for me that make me feel exposed and pants that are so tight I can barely sit down. I don't want to look like that. It's not me."

"You are right. I have pushed too hard in the past. I can dial it back, but I want to help you see what other people see." She paused and took a deep breath, "I wasn't ready to tell you about this, but I will make you a deal. If you let me help you with clothes and makeup, you go to the gym with me three days a week, and take my advice on boys for the next year, I will pay for you to get the boob job next summer."

I was stunned. It was something that I desperately wanted, but I thought it was years before I would be able to save enough, "Mom, we talked about it after the last consultation. I want it so bad, but we can't afford it."

"You know how when grandma passed, nobody could find her will and your Uncle Bob has been doing all that paperwork for months? All her stuff has been tied up in a legal process called probate. It took months for Uncle Bob to figure out her bills and bank accounts and everything. You know how secretive Grandma was about money."

"We thought she was broke, but it turns out that that she was doing okay. My share won't be crazy, but it will be enough to pay off the car and the bills and set aside some money for Scout for college. We will be better off than we have ever been, and I can help you out more. You will have a few options. You can move to the university after next year and invest the money in school, or you can stay at home and finish at state and get your boobs. It's going to be a few months still, but you will need to choose."

I broke into tears, "Are you serious. We can really do it?"

"Yes honey. We can really do it, but you heard my conditions. I get veto on clothes and you follow my directions on makeup and boys for the next year." I cried nodding my head in agreement.

"I will try mama."

"So, here's the first thing. We are here for 3 more days. Becky and I will get you a chunk of time each day together before you take on kid duty for the evening. I'm not gonna to tell you what to do with your body and a boy, but I think you and River could help each other get some confidence."

"You want me to throw myself at River? That would be so embarrassing!"

"You don't have to throw yourself. Just put yourself out there a little. Show a little interest and see how he responds. If it is awkward, it will be over in a few days, and you can laugh it off before you see him again. On the flip side, you might have some fun. Have you seen his uncles?

"Yeah."

"Are they shy and scrawny and awkward?"

"No. They are scary."

"Honey, those men are hot. Sure they are brutes, but they are hot. Odds are that River is going to fill out and look like them in a few years. He is smart, tall, athletic, and will eventually be muscular and hopefully successful. He needs a big dose of confidence, just like you. He will always be a mama's boy, but that's not so bad for a strong woman."

I knew there was no arguing with her about this, so I didn't try. River wasn't interested, so it wouldn't be too big a deal.

"Ok. We can try. What do I have to do?"

"That's my girl! In the morning, we need to go hit the store and see if we can find a reasonably priced swimsuit and grab a few things."

---

The next morning mom and I went out and bought me a new swimsuit and a few other items. I had planned to spend the afternoon at the beach with River, and she insisted that I wear the new bikini instead of my usual board shorts and swim top. We couldn't find the same pattern for my top and bottom, so the pieces didn't match, but we found some complementary colors that I liked. The top had lots of structure, so I didn't feel like my little boobs were on display. The bottoms were normal bikini cut, and covered me ok with some adjustment. Because of the shape of my butt, as I walked they gradually wedging themselves between my cheeks and I had to readjust frequently or put up with it. At least it wasn't a thong.

I messaged River in the morning and asked him if he wanted to hit the beach after lunch. I comforted myself thinking that with all the beautiful women on the beach, he would be distracted and might not even notice me. I could hide on my towel if I wanted and watch the cute guys strut past.

When we got to the beach I took a deep breath and removed my cover dress, River tried hard, but he totally stared.

"What I asked?" panic clearly in my voice. "Does this swimsuit look bad? My mom picked it out. She pretty much insisted I wear it at least once on this trip." I explained by way of an excuse as I spiraled.

River saw the panic building on my face, "No. It looks great! Sorry, I mean you look great. Like terrific. I just haven't seen you in a normal swimsuit for a couple of years." He stammered. It was so super awkward but I felt better.

He then took off his shirt, and I was surprised to see a full six pack of abs and some definition to his pecs. He was still skinny, but there were more muscles than last year. He was better to look at than I had remembered.

My mom had insisted on a few things for today, I had to wear the new swimsuit, she got to put some subtle makeup on me, and I had to ask him to help with my sunscreen. At first, I thought she meant 'everywhere' and I was scandalized, but she clarified that just having him sunscreen my back would be plenty.

As I got out the sunscreen River said, "Oh I totally forgot. Can I borrow some of that?".

"Sure" I said, "but only if you do my back."

He waited and tried not to stare, but I had his attention as I slowly did my legs and arms and butt and then my belly and chest and face. I felt embarrassed and thrilled to have his attention on me. I then turned my back to him and said, "Back please." I was nervous to have him touch me, but this was going like exactly the way my mom had said it would. I hate it when she is right.

The cream always feels so much colder when someone else does it and I instantly broke out into gooseflesh despite the heat of the Florida sun. He slowly massaged the cream into my skin taking longer than was strictly needed. His big hands felt good rubbing my back. As he finished up, I asked if I still had any white spots on me.

"A couple." He said.

"That's not helpful. Can you get them?"

"Um ok." He responded.

He bent over and rubbed a few spots on my calf and then a spot on my thigh and then a spot on my butt that was partially covered by my suit. I was so surprised when he touched my butt that I jerked and stumbled back into him. He caught me by the waist and shoulders, but my back had pushed into his crotch. I was pretty sure I had felt his hard penis briefly press against me.

I said "Oh my god, I am so sorry that I ran into you, you surprised me!". As I turned around, he confirmed that he had an erection, because he immediately turned away and bent at the waist to hide the bulge in his shorts.

I pretended I hadn't noticed. "Want me to do your back?" I didn't wait for his response and immediately started lathering his back. I felt a bit mischievous taking my time to explore the surprising amount of muscle in his shoulder and arms. I wondered if my touching him was keeping him aroused. The moment I finished he plopped down onto the sand and covered his lap with his towel and did his sunscreen from a seated position while I fussed with my hair. I smirked to myself about getting River excited.

There were plenty of attractive people for us to ogle on the beach. We enjoyed the people watching and making up stories for them as we listened to some music. It was just like every year, River and I enjoy each other's company. I loved the warm bath temperature water and spent way too long splashing and enjoying the calm waves. As the day wore on, I forgot to be embarrassed about my swimsuit. I enjoyed how bad River was about checking me out and trying to act like he wasn't.

As it got hotter in the late afternoon, I suggested that we go to my room for a cold drink from our fridge before we met up with the family at the pool. As we walked into the hotel, River said, "Bella, that swimsuit really fits you and you look great. Why do you usually choose suits that have more coverage?"

I blushed and said, "I usually don't like feeling exposed. I get embarrassed and self-conscious."

As we got to the room, he continued. "Oh, yeah that makes sense. It's personal choice. But you look really good! I don't think you have anything to be self-conscious about."

I know he was trying to be nice, but I couldn't stop myself from tearing up. "Thanks River, but this top is a lie. It's all padding to give me the look of boobs I don't have."

"I think that is pretty normal. Lots of girls wear pushups and padded tops."

"It's not just that. I don't really want to talk about it." I was really embarrassed about this turn in the discussion.

"I told you about my dick not working and then being mocked for it. It can't be worse than that!" he insisted pushing the issue.

I thought about that for a moment as I grabbed a couple of diet 7-Ups and poured them it glasses with some ice from the ice bucket. It was time to be brave.

"Do you promise not to laugh or judge or tell anyone or even talk about this again if I show you?"

"Sure. You can trust me Bella. Besides, who would I tell?"

"I am serious River. Nobody ever."

"Sure Bella. We have known each other our entire lives. You don't have to be embarrassed with me."

"Ok. So, like my boobs aren't normal." I started. "The doctors say they are in the normal range and I have seen pictures, but they aren't like most normal boobs, and I don't really like them. That's why I like to stay covered up."

I looked him in the eye and decided that I could trust him so I decided to bite the bullet. I pulled my coverup over my head and then reached back to unclip my top. Once I had it unclipped, I held the cups against my chest and said more aggressively than I intended, "Remember, you promised River. No teasing. Not ever about this!"

As I pulled my top away, River was the first boy to ever see my breasts. He saw that they were small but one was noticeably bigger than the other. He saw that they were pointy ending in large nipples. He saw my areolas were puffy and huge. I am sure he saw why I was gross and would finally understand.

"Oh!" he said. "I've seen boobs like yours before."

"You have?" I was shocked.

"Yeah, I mean not in person. In real life, I have only seen my mom and a girl at the water park last year, so not really a range for comparison. But there is a Reddit for girls with puffy nipples and a lot of the girls have boobs like yours. Some guys are really into it."

"How is that even a thing! Can you show me?" I asked. I had seen some pictures, but I didn't realize that there was a full Reddit for weird boobs.

"Sure, I guess." River kind of shifted around as his erection became more obvious. He looked so uncomfortable. I grinned to myself thinking that he must be sore from spending so much of the day hard.

River adjusted himself again and sat on the side of the bed and started searching on his phone. After a minute he had pulled up Reddit and handed me the phone. I scooted over to look at the pictures with him. He seemed uncomfortable to be looking at these pictures with me, but I want to share this with him.

"Some of the pictures will have more than just boobs, but you can scroll thru and see what I mean." He warned.

As I scrolled, I saw dozens of girls with large puffy areolas and nipples just like mine. Some of the girls were asymmetrical and quite a few were pointy or pendulous. It was like the pictures from the doctor or that my mom had found, but more real because there were dozens. Probably hundreds of girls that looked just like me that had posted pictures of themselves looking sexy. I also saw more than a few naked girls with bare bottoms and waxed pussys and one girl who had posted a picture with herself fully spread open with her fingers.

I paused on that one and passed the phone back to River. "Do you like these photos?"

He looked at the photo and blushed deeply, "Yeah, I mean of course. These girls are hot. I like looking at all kinds of pictures of girls." This whole time, my boobs were still on display, and River wasn't sure if he was still allowed to be looking or trying to be polite and not stare. It was cute and ridiculous considering that we had just shared a moment looking at some girls spread cooch.

"Would you like to touch them River?" I asked.

"Are you sure?" He asked the nerves quaking in his voice.

Remembering my mom's advice I took on a gentle but firm tone, "River, if I ask you to do something, it because I want it done. If I tell you to stop anything ever, you do it. Now come on and cowboy up." It came out more direct than I had intended, but River responded immediately by turning and softly cupping my breast, touching each one in turn. He traced around my areolas and ran his rough thumbs over my nipples.

"Gentle, my nipples are really sensitive." I said. At first, I was so self-conscious that I didn't really feel his touch, but as I settled down, I realized it was nice to have a guy touching me, even if it was just River. As my nipples started to get harder, I felt tender and overly stimulated, so I brushed his hand away and grabbed my swimsuit top and slipped it back on. He looked at me trying to understand what was going on.

"Your turn. Will you get it out for me?"

"I am hard. Are you..." he started once again to question my request, but I gave him a stern look with raised eyebrows and he cut himself off. He stood and undid the ties on his swim trunks. As he dropped his trunks his mostly hard dick popped out, bobbing about two feet from my face. The tip was dripping with precum.

I reached out and grabbed it as a handle, pulling him closer, and then started stroking it. I had some practice with this, and I figured he would finish pretty fast. As I touched him, he started to get soft.

"River do you not like girls? What is it?"

"You said no teasing." He said clearly upset. "Just stop it, Bella. It is no use."

"Is it ok if I just touch you a bit? Tell me what's going on when this happens?" I asked.

"Seriously, I really, really, really like girls." He pleaded. "Touching your boobs was amazing, but I just get so nervous and in my head. And I worry about what might happen and I worry if I will know what to do, and I worry that 'this' will happen and I will be a disappointment. Every time this happens it gets worse."

I continued to fondle his floppy cock exploring his balls and tracing my finger around the head. The skin was so soft and velvety and he wasn't very hairy so I didn't mind touching him. "I know you got hard touching my boobs. And I felt that you were hard when you put sunscreen on me. What else caused you to get hard today?"

He didn't respond looking mortified.

"Come on River. I have your cock in my hand. Tell why you got hard today."

"Well, umm touching you and doing the sunscreen was nice and when you did my back that was good too. Do you remember when you walked down to the water the first time? As you walked away, your bottoms rode up and your butt wiggles when you walk. The way your hips sway is really sexy and I was looking at your bottom and that got me hard and I had to wait a few minutes before I could come out and join you." I was surprised by that. I had expected him to describe some other girl at the beach or something. I never thought that boys would like my big butt.

"What else. Did anything else about me get you hard today?" I could feel that River was starting to firm up in my hand and I resumed stroking him. I liked hearing him tell me I was sexy.

"Well when we got back from swimming, you were sunning on your back and you had your legs parted. With the swimsuit all wet, it clung to you and kind of outlined the shape of your um you know."

"You mean you could see the outline of my labia? You like looking at girls pussys River. Is that what you are into?"

"Um yeah. I knew I shouldn't stare, but I had a hard time looking away. You are so feminine and pretty." River was now rock hard as I stroked him. I had only touched two other dicks, but River's seemed perfectly normal. It was basically the same size and shape as the other guys I touched. He wasn't too big or small anything, and I liked that he was circumcised.

"Tell me when you are going to cum so that I can catch it with my hand. We can't get any on the bed."

"I am close. Oh, ok now." He said and immediately starting throbbing in my hand. I knew from getting hit in the face previously to shield the tip with my hand at first. I stroked him lightly though his orgasm catching the cum in my hand. By the time he was done, my hands were coated in jizz.

"That was really great. Thank you." He said looking dazed.

"You are welcome River. Now maybe you can avoid embarrassing yourself at the pool. I told my mom we would meet them down there for snacks about 5 minutes ago. It's ok if you look at my butt, just don't be obvious ok?"

---

Once we got downstairs, we were immediately charged with managing my and River's sisters so that our moms could hit some bars and go dancing. The girls were both 8 years old and loved these annual trips. We all played in the pool into the late evening and then we shared a pizza. We walked to a nearby shopping area and got ice creams and the kids played hide a seek in the plaza. We knew that our mothers wouldn't be home until late and they would almost certainly be drunk unless they met someone in the bar and found something else to do. They sometimes would call River to come walk them home if they were too drunk to be alone. We got the girls to bed together in my room and then hung out chatting in River's room. I cuddled against River in my comfy sweatshirt watching TV until around 11 when I headed to bed.

The next morning, we met up and got the kids some pancakes at a nearby diner while the moms slept in. Around noon, the women were mostly recovered from their hangovers and ready to take over kid duty.

As I was getting ready to head over to River's room and come up with a plan for the day, my mom and I shared the mirror. "Bella, how did it go yesterday? Did he notice your makeup and the swimsuit?"

"Mom, he is a boy. There is little chance he realized the makeup was different, but he definitely noticed the swimsuit. Actually, I liked it too." I paused and then admitted. "You were right. Everything you said would work, worked."

She took the acknowledgement and didn't rub it in. "Did you guys 'do' anything?"

"Not much." I blushed than I blurted out. "I let him see my boobs and he was really nice about them. He got so hard seeing my tits that I helped him with my hand."

"That's great honey! You were brave and it worked out. Did you want more?"

"Not yet."

"See honey. A boy like River is glad to see any boobs. If you set expectations, boys are less picky than you would expect. I am so happy for you! What's the plan for today?"

"Probably take a long walk down the beach and look at the stores on the way back. What time do we need to be back?"

"How about 7 pm? I have a couple of bucks in my wallet if you guys want a cold drink while you are out. We will be out of the room pretty quick if you don't want to rush out right away. I picked out your outfit already. Now let's see about your makeup."

"Mom!" I started to complain. She was acting like I was the same age as my sister.

"Nope. You can shut that. The deal is I get to help with your makeup and pick out your clothes." She said sternly. "If you get bored of River, I am sure you can walk down the beach and find plenty of boys that want to chat."

"Yes mam." I conceded. This deal was going to be tough.

Once we were ready, I walked with my mom and sister over to River's room. I could hear his sister singing loudly with the TV and I was glad I didn't have to join them for the craft activity they have planned for today. River was ready and pushed out the door the second he saw me.

"You ready?" he asked.

"Sure. Actually, I forgot something at my room. Mind if we go by there real quick?"

I was wearing the same swimsuit, my only bikini, with a loose strappy tank top and some cotton shorts. The shorts weren't cheeky but they were short compared to my usual choice. They were cute and had semi-usable pockets.

When we got to my room, I sat on the side of the bed and asked River to come join me. "I was thinking about what you said the other day about how I am giving mixed messages to boys." I was pretty embarrassed, but I also wanted this to work.

"If I wanted to tell a guy that I didn't want my boobs touched, but it is ok to touch me on my underwear inside my pants, what would I do?"

River was struck dumb but recovered after a moment. "I mean, the clearest thing would be to say something like 'Hey, I don't like having my boobs touched, but other things are ok." He responded.

I stared at him like this was the stupidest thing a boy ever said, and he slowly continued, "If you didn't want to actually say something out loud that was clear and easy to interpret, I guess you could just move his hand from your chest to where you did want it. That would probably work."

"So, let's say your hand was on my boob right here." I reached out and grabbed River's right hand and put it lightly on my chest. "But I didn't want you touching me here, I could just move you hand down here, and you would probably get the message?" I slowly guided River's hand down until his fingers were just inside the elastic waist band of my shorts.

"Yeah, that seems pretty clear." He sort of croaked.

River scooted closer and I leaned back onto my elbows making it easier for him to access inside my shorts. He tentatively pushed his hand down until he met the smooth fabric of my swimsuit bottom. River spent a few minutes lightly caressing over the top and along the edges of my swimsuit exploring the contours of my labia and rubbing over my clit. His lack of experience showed, but it was still nice. River cautiously moved up and kissed me softly on the lips as he continued to rub me. Before I knew it, we were both laying back making out while I ground myself against his hand. I reached down and held his hand in place curling his fingers so that his palm was firm against my clit and labia and his fingers were pressing the fabric of the swimsuit against my vulva. I ground against his hand like this for a minute and then I moved his hand so that I could pull the gusset of the swimsuit to the side and I guided his hand back so that his palm was pressed over my clit and his first two fingers were just inside of me teasing my vulva. I showed him the pace and motion I wanted so that he was pressing and rubbing my clit and labia and penetrating my vulva with his fingertips. "Yes. Just like that. Press hard. Ok. Yeah just like that." As I felt my orgasm approaching. I clenched my legs arching my back holding his hand in place driving his fingers deeper as I ground into him. Finally, I let out an embarrassing low moan as I came.

"Wow. Are you ok?" he asked as I panted.

"Oh, I am good River. I needed that. Thank you."

After I calmed down for a minute, I started to get really embarrassed that I had basically masturbated with his hand, so I said, "I want to get out and walk on the beach a few miles, but we can't go out like that!" I said pointing at the tent in River's shorts. I sat up and motioned for him to take off his shirt and then untied his trunks and pulled out his semi-hard dick. River was much less nervous than he had been yesterday and stayed mostly hard. I slid off the bed and crouched in front of him as I started to stroke him. River probably expected the same basic hand job as yesterday, but I had other ideas.

"I haven't done this before, but I have seen a lot of videos. Just tell me if I need to do anything differently." I said.

I dropped my head into his lap and began licking the sides and length of his shaft. He smelled clean like the hotel soap. When I got to the head I licked the drop of clear precum that was continuously pouring from the tip. As I continued kissing his shaft, I tried to figure out what his precum tasted like. I decided that I couldn't place the flavor, except maybe something briny but I didn't mind it.

"Lay back and enjoy this." I directed.

I then put my hand around the base of his shaft and popped the head into my mouth and tried to coordinate bobbing down on the head with my mouth while stroking the shaft with my hand. I read that I was supposed to use my tongue and to try to suck a little bit, but I also needed to be careful with my teeth. It was overwhelming trying to coordinate all this stuff, so I concentrated on using my lips and tongue on the head and tried to not gag myself. I have no idea how girls take a full penis in their mouths. The flavor of his precum became more pronounced and I could feel him getting bigger and harder. He was hot and hard in my mouth and it was a bizarre experience but also really intimate.

After just a brief minute, River said, "Oh I am close."

Since he was nice enough to warn me, I decided to keep my mouth on it. My mouth was partially filled with his cum when I pulled off and stroked out the rest of his jizz. It was even more than yesterday and the first couple of pulses shot further than I expected coating his chest and belly. Once he was done and so sensitive that he asked me to stop, I swirled the cum around in my mouth trying to get the full taste of it before I swallowed.

'Not great but not horrible' was my first impression. It was a little bitter and salty and maybe weird like raw oysters, but I didn't mind too much except that it really lingered on the palette. In our house, I learned to eat plenty of things that weren't always great. Considering the mess, I kinda wished I had taken it all in my mouth because now I was worried that I might have some on my clothes. Note to self for next time.

"Come on River. Get yourself wiped off in the bathroom and go pee if you need to, then let's get out of here." I washed my hands and rinsed my mouth grabbing a stick of gum from my bag while he wiped himself off.

---

We initially had a lovely day strolling down the beach. We stopped for a bit to watch two mixed pairs playing beach volleyball. The girls and guys were both super good looking and I didn't mind watching the game for a bit. I could tell that River wanted to play, but there wasn't an opportunity. After 2 hours of walking, we stopped to share a can of iced tea from a market then headed back. About halfway back to the hotel, we ran into a pair of young guys playing catch with a nerf football. They were both shorter than River but cut and athletic looking. River caught a wayward pass as we were walking by, and they invited us to play some 2v2 touch football. I could throw a Nerf ball ok and River could catch anything. Despite the guy's effort, the game was close.

As the game went on, the guys started getting handsy with me, 'accidentally' grabbing my butt and that sort of thing. They were also talking some shit to River but making it seem like they were kidding around. At first, I thought it was fun, and River hadn't noticed them grabbing me, but I started to feel uncomfortable and told River that it was time for us to get back.

"Last point!" River called

I pitched the football to him, and he made a catch running 25 yards to the "end zone" they had marked in the sand. Instead of letting it go, the defender tripped River from behind causing River to face plant into the beach. "Take that bitch!" the guy yelled kicking sand in River's face. I guess he didn't like getting beat and wanted a fight.

At the same time, the guy defending me made like he was going to tackle me and grabbed me around the waist and started pawing at my chest trying to pop my bikini top up over my boobs. I was stunned but then started to struggle against him and screamed as loud as I could, "Don't fucking touch me!"

Pulling himself up caked in sweat and sand, River turned his face to see the me being held. In just an instant, River was up and crossed the distance to us. The guy holding me let go as River flew at us. He took a swing hitting River in the jaw and neck, but River dropped his shoulder and plowed into him slamming him to the ground and then stomped on the guys arm with a sickening crack. The other guy was just a few steps behind River and River immediately took a kick to the ribs and then deflected a punch using his reach to tie the guy up. They grappled for a bit but River gradually got him into a choke holding the guys feet off the ground as he pulled an arm bar across the guys throat. The guy rapidly went from elbowing River and trying to hit his face to turning purple and panicking as River strangled the life out of him. River was shaking him and crushing his throat with his full strength. His friend just laid on the sand clutching his broken arm screaming unaware that River was about to kill his stupid fucking friend. I stood stunned for just a minute before reality slammed home.

The guy stared at me his eye bulging and his face turned a bright purple except for the spittle around his mouth. I thought to myself 'fuck you!' but then I thought of River and that he didn't want to do this.

"River, let it go. Come on River it's over. Let him go." I yelled at River. As the guy went limp, River finally heard me and let the guy go shoving him to the ground where the asshole lay wheezing and retching.

"Come on River, we need to get out of here."

"We are going the wrong way." River looked around dazed. I think we were both in shock at how the situation had turned violent so fast. A group of people had been watching but nobody reacted or had tried to help us.

"I know", I whispered. "We are going to take some detours just in case. You fucked those guys up and there were a bunch of witnesses. The police might come looking."

Once we got a few hundred yards up the beach I led us out to the street and we paused to put on our clothes to change our appearance. We looped back in the correct direction and headed through a shopping district cutting through stores and trying to get lost in the crowd.

"I am sorry I freaked out River. That fucking asshole was trying to expose my tits to humiliate me. I kind of lost it. Are you ok? They hit you a few times."

"It's ok Bella. You did exactly the right thing standing up for yourself. If someone is assaulting you, you always scream for help while you can." River pulled me into a side hug as we walked. "Yeah, I am ok. My jaw is sore and my ribs really hurt, but nothing feels broken. Just bruised." He then said quietly, "Thank you for stopping me."

"Yeah. Do you think you would have...", I didn't finish.

"I don't know. Maybe? I was so angry. I hate bullies so much."

We walked quietly for awhile. He eventually said, "Did you know that my mom was attacked once? I found out about it last year. I was asking about my grandparents and Uncle Charlie thought it was time I knew the full story. This guy beat her up and raped her. They never figured out who it was."

We walked quietly for a bit as I processed.

"I was born 9 months later."

I felt so disgusted that something like that could happen. A wonderful woman I love was violated and then she carried that baby. River had that monster as a father. I had no idea how this must make River feel.

"Her parents guilted her into keeping me, because of the church you know. But they always acted like it was her fault and they treated her like shit. They never helped us or wanted to see me. That's why my mom and uncles won't see them. Anyway, your mom got pregnant with you as soon as she found out, so that my mom wouldn't be alone. Uncle Charlie said that your mom was an angel." He said quietly.

"No." I corrected him. "My mom always told me that I was a happy accident." I started to cry, I was so confused. My mom had lied to me but had been so incredible for her friend.

"My mom is kind of a slut, she's no angel." I tried to joke through a sniffle, but it didn't land.

"Bella, it wasn't an accident. Your mom knew what she was doing and why. When I talked with my mom about it, she said that having your mom go through it with her and having babies together saved her life."

"Why do you think she never told me? I mean my Dad is a deadbeat, so she didn't really need to keep this a secret."

"When we were little, do you think we would have understood?"

"No, I guess not."

We finished our meandering trip back mostly in silence walking hand in hand.

---

"River, we have a half an hour before we are supposed to meet the family downstairs. Will you come to my room?"

I could tell that River's jaw was hurting him and he was moving stiffly from the sore ribs. When we got to the room, I turned the bolt on the door and then pulled River into a hug.

"Not too hard on the ribs" he winced.

I let go and looked him in the eye. "River, the way you stood up for me today was incredible. I never expected anyone would.... Well. I want you to know that I really want this. Would you go to bed with me? I know this is weird and a crazy day, but my period is probably going to start tonight or tomorrow, and I want this for us."

"Bella, what if it changes something?"

"I need to change. I think we both do, but I promise this won't break our friendship."

River looked down into my eyes to see my confident appeal, searching to make sure it was the right this to do. I felt so vulnerable asking for this and I was afraid he wouldn't want me, but then he scooped me into a big hug and deep kiss. After a moment, he broke the kiss and asked, "Which bed?"

"This one. I am going to put a towel down so that we don't get anything on the blanket."

I laid out a towel on the bed and then dropped my shorts and swimsuit bottoms to the floor. I took off my shirt and reluctantly removed my swimsuit top. I was standing fully nude in front of a boy for the first time.

"You are beautiful Bella." He said shyly.

River pulled off his shirt and dropped his trunks revealing his mostly hard cock. I climbed on the bed and centered myself on the towel.

"I am ready. Just get up here."

I could feel River's gaze as he took the view of my breasts resting on my chest, my big nipples hard in arousal. I saw his eyes trace over my lightly defined abs and continued to the top of my dark curly pubic hair that I kept trimmed around the edges framing my large labia. I could see the doubts starting to form on his face as the magnitude of the moment set in. His manhood started to drop as he stood paralyzed.

I watched this all play across his face and trying to keep the hurt from my voice I asked gently, "River, do you want me?"

"Yes, Bella. So much."

"Then get over here."

"But it is gone soft again." He pleaded with embarrassment.

"It's ok. Just get between my legs and touch me. Rub my pussy with your cock." I didn't really know what to do for River, but I hoped that having him touch and give me pleasure would give him some confidence.

River did as instructed and was soon crouched between my legs exploring my pussy. He rubbed the head of his penis over my labia and clit spreading my lubrication and building my anticipation for having him inside me. His cock felt some hot on my clit and I was nervous, almost trembling, but I found that I wanted him so bad I would do almost anything.

"Did my ass look good in the swimsuit today?" I asked.

"Yes. That swimsuit looks so good on you. I got really distracted watching you walk."

"Do you like the way my butt jiggles when I walk?"

"Yes, you are so sexy."

"Suck on my tits while you rub me. They are sensitive, so be gentle."

My tits were so tender and sensitive with my impending cycle, but River did his best to be gentle. The feelings were so intense, a mix of pain and electric pleasure pulsing through me as River did his best to get his lips over my puffy areola and gently sucked my nipple. I continued in a husky whisper, "You know what got me hot River? You stood up for me and protected me. I felt like you would have killed those guys if you had to. That was so fucking sexy River. It is the hottest thing I can imagine. I know this is your first time. Mine too, but I want this so bad."

While I spoke in his ear his body finally started to respond and he was soon getting hard. I felt it as he rubbed on me, so I reached down and placed his head in my entrance.

"Try to push into me. Go slow."

River had to use his hand to keep his dick from bending as he tried to push in, but I felt the head gradually stretching me open. He got progressively bigger and harder as he worked his way into my body. He was cautious and gentle pushing in a bit at a time before backing and pushing just a bit deeper each stroke. The heat and tightness in my core were overwhelming for me. He kept going slow and was sensitive to the resistance he felt from my body.

I had expected it to hurt, but initially it wasn't much different from my fingers or the handle of my hairbrush. His cock was hotter inside me and I felt fuller but it was comfortable and nice. I was sharing this with a boy that cared for me and it felt special. As he slowly pushed into me, I felt his warmth and intrusion stretching and hitting nerves I had never felt before. Gradually, I understood that this was different. He was penetrating my sense of being and I couldn't think about anything other than the feeling of my clit and that stretching hot pressure filling me up. My nose was full of his scent, and my body pinned by his weight holding his cock buried inside me. I hadn't realized until this moment that I was surrendering myself to him.

"Slow." I pleaded as it was suddenly tight and uncomfortable. He was deeper than I had ever had anything inside me before and suddenly my body resisted as his cock forced me to accommodate him. He immediately backed off, easing into me gradually giving me time to adjust. I looked into his eyes grateful for his patience and I saw his love and I knew I could trust him. With a last small push, he was fully inside me and our bodies joined. As he bottomed out, a pain almost took my breath away causing me to squeal slightly. It was too tight, too deep. I needed him to back off. I reached down and guided his hips back slightly.

"It's ok, just pull out just a bit. Not so deep. Try not to go all the way in, at least at first." I asked.

I put my hands on his hips and guided him out half an inch and then held him in place taking a moment to adjust to his body and take in the experience as the pain passed.

"Ok you can move a bit. Go slow."

"I don't know how long I can last." he said looking worried.

"That's ok. I don't need it to last this time. Just be gentle."

I tried to guide River's hips as he started to move, pulling a small way out before pushing back into me. He was careful not to push too deep and I felt my body relaxing. As we found a slow rhythm I let him take charge setting the pace.

"I like that pressure of your hips against me."

I surrendered to this man on top of me and started to feel the pleasure his body was giving me. River experimented with rocking his hips to keep pressure against my clit while pumping himself into me. He got better as he found a rhythm. I was feeling a little sore and overwhelmed and I knew I wouldn't be able to cum this time, but I felt a deep satisfaction.

"I'm close." He said.

"Cum inside me."

Hearing this, immediately set him off and he buried himself into me deeper than before. I gave off a guttural moan as I was stretched with him pushing to full depth as he pulsed inside of me. This time it didn't hurt, but I was completely overwhelmed as I dominated by his body. This loving man had fully penetrated me to my core and was filling my womb. I had never imagined I would love the feeling of a man cumming inside me, but I was feeling a deep primal pleasure and inexplicable emotions with his orgasm. I felt satisfied and loved.

As his orgasm abated, I pulled him into me. "Stay like this." I ground my clit into him holding him in place experimenting for a moment with the depth of his penetration and I knew with a bit of practice, I would cum really hard. I then relaxed and let him hold me.

For just a moment my mind wandered, and I fantasized that he had just gotten me pregnant and what our baby would smell like. It scared me that it felt so right and easy to disappear into the idea. As he started to soften inside me, I shook off the fantasy and gave him a kiss.

"I am sorry you didn't cum too." He said. "Is there anything I can do for you?"

"It's ok. This was enough. You made me feel really good."

He rolled off of taking some breaths. Now that he was out of me, I felt empty and missed his presence. I could also feel his cum leaking out of me and I knew that we were expected downstairs soon. I hopped up and headed to the bathroom.

"Get up lazy bones. We need to get downstairs. Be ready to go in five minutes."

---

When we got downstairs, my mom took one look at us and gave me a knowing smile and then looked at River's mom and gave her a wink. "It's about time you guys joined us! We were started to wonder if you decided to run away."

We hung out a bit as I explained what happened with the guys on the beach. River's mom made a big deal out of it and said how proud she was of both of us. I soft sold the degree to which River had nearly killed the one guy, but they didn't seem concerned that he messed them up and the police might be looking for us. They agreed we should probably avoid the beach for the remainder of our trip which sucked, but at least there was a pool.

After dinner, I had a few minutes with my mom as she changed into her evening wear. "Are you ok honey? Were you scared when the guys were fighting?"

"I am fine. I was freaked out when that guy was grabbing me, but River was there so fast." I paused and confided, "He almost killed that guy, like for real."

"Did River scare you?"

"No. He would do anything for me." I blushed. I was thinking about how hot I had gotten seeing him defend me.

She gave me a knowing look nodding at my words. "So, how was it Bella? Was he good to you?"

"How could you tell?"

"A mother knows. You both had a glow."

"He was so gentle and kind mom. He made me feel good and it was perfect. Until this afternoon, I wasn't going to go all the way with him. But then I couldn't wait another minute."

"Honey, welcome to being a woman. That's how it is sometimes. Do you want to do it with him again?"

"Yes, but my period is probably coming."

"Well, that might be for the best. Take care of him for the rest of the trip, but you guys need to make a clean friendly break. You can't be trying to seriously date this year, school's too important."

"What if he meets someone else?"

"Don't worry honey. If you can stay friends and you will always be there for each other."