There is a fair amount of backstory and set up to this story. I hope you’ll read it but if you want to skip to the naughty part scroll down until you see ##########.
When I was 25 I went through a really tough break up. I had been with my ex for about 8 months and I was head over heels in love when out of the blue (to me at least) she dumped me. Her name was Natalie. She was very religious and I am not. She was very fit and a vegan and I am a bit of a chubby nerd with self esteem issues who at the time didn’t even know how to cook. Now that I type it out… I probably should’ve seen it coming.
The love that I felt probably had more to do with the fact that sex with Natalie was the best sex I’d ever had. We met through a dating app and she was the most conventionally physically attractive girlfriend I’d probably ever had except for maybe my high school girlfriend. She was really fit with short blonde hair and perky little A cup titties and a round athletic ass.
If you follow my posts you will see that I’ve had a lot of experiences but in reality they were all a lot of one time experiences. I had the occasional girlfriends and while I certainly found them attractive, they were in my league and Natalie was probably a little out of my league. Or at least that was my thought process at the time.
Me being someone who is very experienced, Natalie still found ways to blow my mind. I explain this to illustrate just how crestfallen I was when we broke up because this isn’t a story about Natalie. This is a story about Hannah…
After Natalie and I broke up I was really depressed and indulged in some unhealthy behaviors. I was sitting at my desk at work day after day literally holding back tears so as not to freak out my coworkers. I texted former friends with benefits to try and find some comfort (some who were mentioned in my previous posts) and they were either not interested or had boyfriends. So I decided to turn my online dating profile back on.
About 2 weeks later I got an alert on my phone while I was sitting at work that I’d received a message on the app. I checked the message and it was this girl named Hannah. She was 28, had a nice smile with long brown hair, and I could tell from her photos that she was on the chubby side. I want to make it clear that it didn’t bother me at all. As I stated, I’m a chubby guy myself. The reason I specify this point is because our shared experience over our insecurities and body image issues was part of how Hannah and I bonded.
Also, I like a nice face and a nice smile and she had that. It didn’t hurt that I’m a “boob man” too and Hannah appeared to be gifted in that department based on a photo in her profile that prominently displayed her cleavage. Kind of a busty Aidy Bryant if you want a celebrity reference.
We started chatting and it was a welcome distraction from my post break up depression. We had good texting chemistry. She had a great sense of humor and her meme game was on point. She had recently moved to the area and had been going to a local trivia night to meet people. A few days later we decided we should meet up for an in person date and she suggested we go play trivia at this place she had found.
My post break up depression would come in waves and a few days before our date I legitimately accidentally texted my ex. I know it sounds like I did it on purpose but I swear it was an accident. I mean to text my other friend and didn’t realize I had made the mistake until I received the response from Natalie. We chatted for a few and I tried desperately to convince her it was truly an accident and she probably still doesn’t believe me. I was mortified and sank into a really low depression. My depression was bad enough that I messaged Hannah and explained that I thought she was really nice and that I was looking forward to meeting her but that I’m still dealing with really profound sadness over my break up and that I didn’t want to lead her on because I was a mess.
It was really important to me that I make clear to Hannah that this had nothing to do with her and that she had done nothing wrong so I went as far as telling her how I’d just accidentally texted my ex and how the embarrassment had sent me spiraling. Hannah kindly said she totally understood and that she appreciated me being honest with her. She told me she hoped I would feel better soon. Then she told me since she was new to the area and didn’t know many people besides her coworkers, she would love to keep chatting as friends. I said that’d be nice (but I assumed we’d probably never talk again).
A few days later I received a text from Hannah with a meme that referenced something we had joked about previously. I replied with a joke and we chatted a bit more and then the conversation ended. It was a perfectly pleasant interaction.
A few days after that she sent me a pic. It was a selfie at the bar where she played trivia. She had come in third place with a group she had met there and wanted to brag about it. I replied and told her if I had been there we would have won first place, guaranteed. We chatted a bit longer that night. The conversation was a bit more flirty but still pretty innocent.
Things went on like that for a few weeks. She would text me and we’d chat and the conversations got longer and longer. We started sharing stories and getting to know each other better and one night she got the nerve to ask me about my break up. I told her the whole story and about how blindsided I was.
“Do you mind if I ask what was it about her that made you fall so hard?” Hannah asked.
At that moment I struggled to give a good answer. Natalie wasn’t, like, super funny. We didn’t share a lot of interests. So my answer was kind of more broadly about how I felt being with her. In hindsight it was as if Natalie was more of a status symbol for me being an insecure chubby guy because we really didn’t have anything in common.
Hannah just replied, “Interesting.”
Then she asked, “So she was like super religious?”
“Yeah, very big into Jesus. Not really my bag but I didn’t mind that she was into it. She was very politically liberal which we did have in common,” I answered.
“Sooo was she one of those waiting for marriage types?” Hannah asked.
“Not at ALL lol,” I replied.
Hannah texted back, “HAHAHA, those repressed church girls can be pretty wild or so I’ve heard.”
“You have NO IDEA,” I responded.
“What? Was she a dominatrix or something?!” Hannah asked.
“No, nothing like that. Not sure how to elaborate without sharing details you may be offended by lol,” I texted back.
“I won’t get offended!” Hannah insisted.
“Are you sure?” I double checked.
“Positive,” she replied.
I then recounted to Hannah how, “a few weeks after Natalie and I started having sex and we had become an official couple, Natalie insisted we both get STD tests because she hated condoms. I have always been pretty good about using condoms and don’t have a lot of experience of sex without them. I didn’t object to getting tested and there weren’t any issues with either or our tests. Since she was on birth control we started having sex without a condom. That being said I always pulled out when I came because I thought that was somehow being extra safe. One night we were having sex and when I was getting close I warned her I was going to cum and she said cum inside me and insisted I not stop fucking her. It was really intense. I’ve never cum inside a girl while not wearing a condom. Probably not that wild by most people’s standards but it was an intense experience for me.”
“Wow…” Hannah texted.
“TMI?” I worried.
“Not at all! I can see how that would be intense,” she assured me.
“Ok glad you aren’t offended,” I said, relieved.
“Eh it would take more than that to offend me,” Hannah replied.
“Have you ever had that intensity with someone?” I asked.
“Soooo… can I tell you something and you promise not to judge me?” she responded.
“Of course,”
“I’ve actually never had sex before…” Hannah admitted.
“Really?” I replied.
“Really,” she confirmed.
“Why would I judge you for that?” I asked.
“I don’t know. Just didn’t want you to think I’m some kind of weirdo,” she explained.
“I would never think that. Everyone has their own path. If you don’t want to, you don’t have to,” I assured her.
“Well it’s not that I don’t WANT to, I’ve just never really had a boyfriend,” Hannah texted back.
“You’ve never had a boyfriend?”
“I mean I went out with a guy in high school and I’ve done the dating apps for a while but most guys don’t go for me and the ones who do are creeps,” she elaborated.
“I’m sure lots of decent guys would go for you,” I insisted.
“Most guys want some tiny little princess and I’ve always been a bigger girl. I think they just aren’t attracted to me,” Hannah said.
“I’m certain that isn’t true. I think you’re very attractive. Everyone is different. I felt that way about myself for a long time but I eventually realized I wasn’t really putting myself out there. I expected everyone to magically come to me. Once I started putting myself out there I started having much more success in dating. I don’t know if that’s helpful or not,” I replied.
“Well I feel like I HAVE put myself out there. I mean, I messaged YOU on the app,” she followed up.
“Well I’m sorry that is how you feel. From my outside opinion, I think you are very nice, I think you have a great smile, and you are blessed with rocking cleavage!” I said playfully.
“Lol how do you know I have rocking cleavage?!” she asked.
I screenshot the profile pic that showed her cleavage and sent it to her with a “😳” emoji.
“Lol oh yeah… I forgot about that,” she said bashfully.
“I mean it’s a good thing we didn’t go on that date. I’d be thinking about motorboating you all night. I wouldn’t be able to concentrate!” I teased.
“Omg shut up! Lol” Hannah texted back.
“Also you don’t need a boyfriend to hook up. You went to college. Haven’t you ever gotten drunk at a party and hooked up with a guy in a closet or something?” I asked.
“Well…” she replied.
“I KNEW IT!” I shot back.
“Ok ok. We didn’t have sex or anything but a couple years ago my college roommate got married. I met a guy at the reception and we got super drunk and I ended up going back to his hotel room,” Hannah said.
“Oh yeah? Care to share any of the lurid details?” I asked.
“Soo he was sharing a room with another guy who he traveled to the wedding with so we ended up getting interrupted before things could go too far,” she explained.
“Are you comfortable sharing how far it DID go?”
“Sooo… we made out and he was rubbing my clit over my panties,” Hannah elaborated.
“Is that all?” I asked.
“Annnnnd I jerked him off,” Hannah finally confessed.
“Hannah you SLUT!” I teased.
“I know, I know but he lived on the other side of the country so it was a one time thing,” she said.
“Just to be clear I was totally kidding,” I clarified.
“I know, silly 😜,” she assured me.
After that conversation we started talking a little more often. The conversations would always start out innocuous but would quickly turn to focus on sex. I want to be clear we weren’t sexting. Just talking about sex. She would ask me all kinds of questions and I would tell her stories, some of which I’ve posted here. She would even tell me about other guys she met through the app. She told me how she was planning to wear her “fancy” bra for a date with a guy who was going to meet her for trivia named Alex. She even texted me a pic of her fancy bra laid out on her bed. I teased that my fancy underwear were Superman themed.
“That’s hot,” she said.
The day after her date we were texting again. She told me they did really bad at trivia but that they had a nice time.
“See I told you if I was with you, we’d win first place!” I joked, “Did you take him home and knock boots afterward?”
“You keep saying that but I don’t think that’s true. And no we did not knock boots lol,” Hannah replied.
“So nothing happened? Did he kiss you goodnight?” I inquired.
“We made out in his car a little bit 🤷♀️,” she revealed.
“Well that’s something!” I insisted.
“Eh I don’t know. Wasn’t really feeling it,” Hannah said.
“Well that’s fair but hey look, he was a decent enough guy, right? Sounds like he was into it,” I pushed.
“Yeah he did ask what I was doing this weekend so I might go out with him again,”
“Well good. I hope that works out. Also, yes it is true. If I were on your team for trivia we would dominate and take first place, I guarantee it,” I followed up.
“Yeah sure I’ll believe it when I see it. You’ll have to come prove yourself sometime. Just as friends of course, no pressure,” Hannah texted.
“Yeah maybe we’ll do that,” I said.
“But anything less than first place and you will have let me down,” she teased.
We kept texting throughout the week and all of our conversations continued to quickly turn to the topic of sex.
“Do you watch porn?” Hannah asked.
“Doesn’t everyone?” I replied.
“What kind do you watch?” Hannah texted back.
“Oh I’m pretty basic. I like a good POV blowjob,” I said.
“POV?”
“Point of view so like from the guy’s point of view looking down at the girl,” I explained.
“Oooooh, duh!”
“How about you?” I asked her.
“Nothing crazy. I’m a girl so I enjoy a little more focus on the lady than most stuff that’s out there. I also like to watch anal sometimes,” Hannah revealed.
“Oh wow, that’s a little more advanced than I was expecting,” I said, “Is that something you actually want to try at some point or do you just like watching it?”
“I definitely want to try it someday,” she said matter-of-factly, “I’ve only ever experimented with toys.”
“Well Alex is a lucky man! Hope he’s ready for you!” I teased.
“Haha probably not,” she answered, “Is there something you haven’t done that you want to try?”
“Oh man. Don’t judge me. I’ve always wanted to face fuck a girl and cum on her face. I’m not talking like super aggressively or anything. I know it’s kind of porny but I’ve never done it and I’ve always wanted to try,” I responded.
“No judgment from me. Why haven’t you done it?” Hannah asked.
“I’m too embarrassed to ask. I don’t want to offend the girl or scare her off,” I answered.
“How very gentlemanly of you,” Hannah teased.
Hannah had a second date with Alex on Saturday and texted me that night afterwards. She told me he was nice but he was super boring. She said she tried flirting with him but he was really awkward and she didn’t feel any chemistry. She said he wanted to hang out again but she politely declined.
“I’m sorry it didn’t work out but remember you are absolutely desirable and there are more where he came from who will definitely be interested in you,” I said.
“Aww thank you. You’ve been so sweet. I’m really glad we stayed in touch. I’ve never talked with anyone else about the things we talk about. You make me feel comfortable and I think it’s helping with my confidence. Just want you to know I appreciate you,” she said earnestly.
“The feeling is mutual. Having someone to talk to has really helped take my mind off the break up. So thank YOU,” I replied.
“Of course! I’m glad I could help,” she responded, “But now I have a real problem…”
“What’s that?” I asked.
“Now I don’t have anyone to go to trivia with me this week!” Hannah said, clearly hinting.
“Hannah, I’m not sure it would be a good idea for me to go with. You are doing such a good job getting out there and dating. If we play trivia together and I inevitably win us first place no other man will be able to compare to me in your eyes!” I joked.
“You keep talking a big game about your trivia skills. I’m starting to think you are bluffing!” she shot back at me.
“Oh I don’t fuck around when it comes to trivia. I play to win!” I said playfully.
“You’ve built it up too much now. If we don’t win first place it’ll be a let down,” Hannah replied.
“Oh I guarantee a first place victory,” I insisted.
“You guarantee huh? What happens if we don’t win first place?” she asked.
“If we don’t win first place I will send you a picture of me wearing my fancy Superman underwear,” I answered defiantly.
“Haha well now don’t incentivize me to throw the game!” Hannah teased.
“You wouldn’t dare!” I responded, feigning indignation.
“That’s true, I wouldn’t but you can’t welch on me if we come up short,” she insisted.
“I’m a man of my word,”
The following Tuesday we met in person for the first time at the pub where Hannah liked to play trivia. Trivia started at 7:30pm but we arrived around 6pm. When we saw each other we greeted each other like old friends and hugged. Hannah wore an open button up shirt with a low cut tank top and jeans. Her tits looked much bigger in person. Her photos had not done them justice. We grabbed a table and ordered some food and drinks.
The conversation began with us recounting our workdays. The drinks arrived and we made small talk about what kind of beers we liked. We had two beers before our food even arrived. When our food did arrive we ordered another round. Over the course of the next round of beers she told me she had been nervous to finally meet in person.
“What do YOU have to be nervous about? I’m the one who has to send risque photos if we finish anywhere other than first place!” I laughed.
“This is true. If we don’t win first place you will forever be shamed. You’ll never be able to show your face at another trivia competition and I’ll be making your Superman undies my wallpaper on my phone. Considering we are a two person team and that team over there has four people and that team over there has five, it’s pretty much a foregone conclusion,” Hannah joked.
“Oh ye of little faith,” I replied, “How about this… If we DON’T take first place, I will send you a pic in my superman undies. If we DO take first place, you have to send me a pic in your fancy bra.”
Hannah gasped, pretending to be shocked and offended. She looked around the room and thought about it for a second, “Ok Mr. Smarty Pants, you’re on.”
By the time trivia started we were each 4 beers in. It was us, the four person team, the five person team, an older guy by himself, and another couple. I wasn’t worried about talking a big game. It was all in good fun and I wasn’t nervous to send her a pic if we lost but now I had a big incentive to win. At the halfway point the host read the scores and we were in second place behind the team of four. The second half didn’t go so well and I was sure we were probably falling behind a bit. Didn’t really matter. We kept drinking beer and having a good time. Then we arrived at the final. The host read out the scores and sure enough we had fallen to third place. However, we weren’t completely out of it. We weren’t down by much and for the last question we were allowed to wager as many points as we had. The host gave us the category which was “movie soundtracks.” I got really excited because I am good at both movies and music trivia so I told Hannah we were going all in.
“What if I chose to throw the game and refused to wager any points?” Hannah suggested.
“You gave your word you wouldn’t! And besides, wouldn’t it be epic if we got it right?!” I pleaded.
“Ok fine!” Hannah gave in.
I nearly lost it when I heard the question. It was asking for the song title and artist who performed the theme song from that movie Phenomenon with John Travolta that came out in the 90’s. I immediately knew the answer.
“Sorry, Hannah. I have bad news…We are going to win first place!” I told her and I wrote down the answer… “Change the World” by Eric Clapton.
“Are you sure?” she asked.
“1000%” I said, “Are you sure you can handle paying up?”
Hannah looked at me skeptically and said, “Ok you MIGHT be right but even if you are, one of the other teams could be right too,”
“That’s possible,” I replied, “But the chances of us taking first place just became VERY real so I’m just making sure you aren’t going to welch.”
“I’m no welcher! Now go turn in our answer before we run out of time,” she shot back at me.
I turned in the scrap of paper and returned to my seat and waited anxiously. A minute later the host came on and made the last call for teams to turn in their answers and I could see the five person team was still debating their answer which I took as a good sign. Upon receiving the last team’s paper the host proceeded to tally up the scores and announce the answer.
To Hannah’s chagrin, I was right. She scowled at me as we both anxiously awaited the final scores. In last place was the five person team with zero points. They had bet it all and came up empty handed. In second to last place was the four person team who had been in first place and bet just enough to stay ahead of the five person team should they have doubled their points. The other couple came in 3rd, the old guy by himself came in 2nd, and Hannah and I came in first place! Despite our little competition, Hannah was elated at winning and we both cheered and banged the table.
“That was fucking amazing!” Hannah said as the host dropped off the gift cards we got for winning, “I’ll be right back. I have to go to the bathroom.”
I sat there by myself for a few minutes playing with my phone while I waited when all of a sudden I received a new message from Hannah. I opened it and it’s a picture of her sitting in one of the bathroom stalls with her shirt open, her tank top pulled up and her bra exposed.
“Congrats. Enjoy the spoils!” Hannah said in a follow up text.
I was still staring when Hannah arrived back at the table.
“If you keep staring you’re going to go crossed eyed!” Hannah cautioned.
“Just taking it all in,” I said playfully. “I’ll be right back,” I added as I stood up to go to the bathroom.
I decided to return the favor since she had been a good sport. I walked into the bathroom stall and pulled down my pants. My dick was already hard and poking at the front of my Superman underwear. I took a picture and sent it to Hannah with a text that said, “Now we’re even.”
I went back out to the table and didn’t say anything. She didn’t say anything either. The waiter came by to see if we wanted anything else. I asked Hannah what she wanted to do and she said she wasn’t ready to call it a night but that if she drank anymore she wouldn’t be able to drive home. I pulled out my credit card and gave it to the waiter. Hannah hastily retrieved her wallet from her purse to offer to split the check but the waiter was already gone. She went to put her wallet back and noticed a new message on her phone. I watched as she opened the message.
“HELLO!” she exclaimed dramatically, “Someone is excited!”
“Sorry about that. He has a mind of his own,” I joked.
“Well thank you. This will make a wonderful wallpaper,” she teased.
The waiter brought back my credit card. It was about 9:30pm at that point.
“Are you good to drive? Do you need me to follow you home?” I asked.
“If you wouldn’t mind. Promise you aren’t a murderer?” Hannah asked jokingly.
“I promise,” I answered.
I walked her to her car in the garage and then went and got mine. I pulled up behind her and followed her out of the garage and on to the street. About 5 minutes later we pulled into the parking lot of her building. I parked in a visitor space and got out to say good night.
“I have some really good cider. Did you want to come try some?” Hannah asked before I even had the chance to say goodnight.
“Oooh I love cider,” I said genuinely excited.
##########
I followed Hannah into her apartment. It was a one bedroom on the first floor. She gave me a quick tour that ended in the small dining room off the kitchen. I sat and waited as she retrieved two ciders from her refrigerator. There was a bowl in the center of the table that had a few odds and ends in it like a flash light, some spare change, and a deck of cards. I pulled the cards from the box and started shuffling them.
“You keep these cards handy for all the wild strip poker parties you throw?” I said jokingly.
“Sometimes I like to play solitaire the old fashioned way,” she explained as she brought me my cider, “You know me, I’ve never played strip poker. Have you?”
“A few times,” I confirmed, “Want me to teach you?”
“Sure,” she said enthusiastically.
“Do you know how to play regular poker?” I asked.
“Not really. I could never keep track of all the different hands and which ones are better than others,” she admitted.
“That’s ok,” I said, “I was at a party once where we played strip high card because people there didn’t know how to play poker. All you do is draw a card and whoever has the lower card has to lose a piece of clothing. Want to brave it?”
“I get to cut the deck to make sure you aren’t cheating,” she insisted.
“Fine by me,” I replied as Hannah reached over and cut the deck.
I dealt her the first card and the second to myself. We both sat with our cards face down.
“On three,” I said, “One… Two… Three.”
We both flipped and she had a queen and I had a 4.
“How appropriate… a queen,” she gloated.
I kicked off my socks since I’d left my shoes at the door.
“Don’t get too cocky. We are just getting started,” I cautioned her.
I dealt us two more cards. We counted to three and turned them over. She had a 7 and I had a 9.
“See, that’s karma,” I teased.
“Yeah, yeah,” she replied dismissively as she pulled off her button up shirt.
I dealt us two more cards. We counted to three and turned them over. She had a 10 and I had a 3.
I begrudgingly took off my shirt.
“You are wearing more clothes than me. That’s not fair!” I protested.
“Hey, this is YOUR game. Should’ve thought ahead,” Hannah teased.
I dealt us two more cards. We counted to three and turned them over. She had a 6 and I had a 5.
“Fuck!” I grumbled as I stood up and pulled down my pants exposing my Superman underwear. One more low card and I’d be naked.
I dealt us two more cards. We counted to three and turned them over. She had a jack and I had an ace.
“Yes!” I celebrated.
Hannah rolled her eyes as she stood up and removed her tank top. Her tits were fucking huge and they were spilling over the top of her fancy bra.
I dealt us two more cards. We counted to three and turned them over. She had an 8 and I had a 2.
“Uh oooooh,” Hannah said, knowing I had to get naked.
I stood up across from her, my dick was hard and already straining against the fabric of my underwear. I took a deep breath and pulled my underwear down to my ankles, kicked them off my feet, and stood straight up for a moment with my hard cock on display for her.
“Well, hello,” Hannah said, acknowledging my cock.
I sat back down in my chair.
“So does that mean I win?” Hannah asked.
“Nope. We just keep playing,” I said playfully as I dealt two more cards.
“Oh is that so?” she said, not objecting to the cards I dealt.
We counted to three and turned them over. She had a 4 and I had a 10.
Hannah looked at me sideways then stood up, unbuttoned her jeans and slid them down to the floor before she sat down again.
“We’d be even if you hadn’t cheated by wearing more clothes than me,” I teased.
“I did no such thing,” she defended herself.
I dealt us two more cards. We counted to three and turned them over. She had a 9 and I had a king.
“So long, fancy bra,” I said, waving goodbye as she unclasped her bra in the front.
Next thing I knew, the biggest pair of titties I had ever seen in person spilled out from that fancy bra.
“What do you think?” she asked sarcastically.
“I think they are spectacular,” I responded.
“Shut up,” she laughed.
“Hannah, if you don’t realize you are gifted with amazing tits, I don’t know what to tell you,” I insisted.
I dealt us two more cards. We counted to three and turned them over. She had a 5 and I had another ace.
Hannah shrugged, lifted her butt in her seat and slid her panties to the floor.
“We’re even. Are you happy now?” she asked.
“Oh I’m pleased as punch,” I replied as I dealt two more cards.
“What happens now? We’re both naked,” she observed.
“You’ll see,” I said.
We counted to three and turned them over. She had a 3 and I had a 7.
“What the hell?! That was 4 in a row!” Hannah protested.
“The cards play no favorites,” I said, “I think I’d like to feel your boobs,”
“Oh you would, would you?” Hannah stared me down for a moment and then leaned toward the table and let me squeeze her massive tits.
“Good game,” I laughed.
“Oh my God,” she said, covering her face in embarrassment.
After about 15 seconds of squeezing, Hannah interrupted and said, “Alright, alright. Deal the cards.”
I dealt us two more cards. We counted to three and turned them over. She had a queen and I had a 3.
“Hmmm… I think I’ve got the hang of this. I think you should come suck on these for a little bit,” she said, gesturing to her nipples.
I came around the table, buck naked, and knelt in front of her and sucked her nipples. After a few seconds I teased her clit a little with my spare hand. She let out a light moan and a few seconds later I stopped and returned to my seat.
I dealt us two more cards. We counted to three and turned them over. She had a 6 and I had a 8.
“Hmmm, I think you should come here and suck on this a little bit,” I said, gesturing to my dick.
“That’s what you think, huh?” Hannah said, as she stood up and sauntered naked around the table.
“Yeah I do,” I said as she knelt in front of me.
“For how long?” she asked, looking up at me as she took my hard cock in her hand.
“Hmm… 20 times up and down is a good start,” I clarified.
Hannah took my cock in her mouth and began sucking. She was timid at first. If she was telling the truth, this was her first time giving head. I sat back and relaxed while her head bobbed up and down slowly.
About halfway through she stopped and asked, “Is this ok?”
“You’re doing great,” I reassured her as she went back to sucking my cock.
A few seconds later Hannah stopped and looked up at me with a smile and said, “Ok deal us some more cards.”
I dealt us two more cards as she stood up and went back to her seat. We counted to three and turned them over. She had a king and I had a 2.
“I’m embarrassed to say mine!” she complained.
“You are welcome to pass if you like. I certainly won’t be embarrassed to say mine if I win the next one,” I teased.
“Mhmm, I bet,” she said scowling, “Sooo, I’ve never had someone go down on me…”
“See now you are playing the game!” I said as I stood up and walked my naked self back around the table.
I knelt down in front of her. “Lean back and scoot forward,” I instructed her as I spread her knees apart.
Her pubic hair was neatly groomed. I ran my fingers along her labia and felt how wet she was. I leaned in and kissed her right inner thigh. Then I kissed her on her left inner thigh as I moved closer to her pussy. Then I went back to her right thigh and kissed her right next to her pussy. Then I backed down and kissed a little further down her thigh. Then gave her a gentle bite on her thigh. Not enough to hurt or anything. Then I came up and sucked on her nipples, flicking the tips of her nipples with my tongue. I squeezed her tits as I buried my face in them while sucking her nipples.
“Are you ready?” I asked as I paused to looked up at her.
Hannah’s lips were tensely pressed in anticipation. She nervously nodded her head as she allowed a soft mhmm to escape her lips.
I immediately moved back down to Hannah’s pussy. I traced my tongue along the outside of her labia, gently pushing them apart with my fingers. I then ran my tongue up and down along the insider of Hannah’s labia, tasting her wetness as it coated my mouth and chin. I teased around her clit to build her anticipation. I felt her whole body stiffen when my tongue would come close to her clit. Then I started to slowly and gently massage her clit with the tip of my tongue. First up and down, then I encircled her clit with my tongue.
“Oh fuck,” Hannah let out as I began to massage her clit more firmly with my tongue.
I decided to turn up the intensity and started very rapidly flicking the tip of my tongue up and down on Hannah’s clit using even more pressure. When I did that, Hannah grabbed me by my hair, pulling my face into her and started shaking uncontrollably. I kept massaging her clit as firmly and rapidly as I was physically capable. Hannah’s shaking reached a crescendo.
“I think I’m cumming!” she exclaimed.
I stopped licking her clit and started gently kissing her thighs as her shaking subsided. Her body spasmed once or twice more as I smiled up at her.
“Ok next round,” I said playfully as I got up and made my way back to my seat.
Hannah slunk in her chair as she caught her breath. “Holy shit,” she said as I dealt us two more cards.
When she was composed we counted to three and turned them over. She had a 5 and I had a jack. I stood up and walked back around to her. I took her hands and pulled her forward, guiding her to her knees.
“I want you to suck my cock some more,” I said as I presented my hard dick right in front of her face.
Hannah didn’t hesitate and immediately started sucking my cock again. This time with more confidence.
“Is it ok if I fuck your mouth a little bit?” I asked, not really sure of a nice way to word it.
“Mhmm,” she mumbled with my cock still in her mouth.
I put my hand on the back of Hannah’s head and began lightly thrusting my hips, pushing my cock into the back of her mouth. Hannah gasped for air between each thrust. I went a little more aggressively but was careful not to go too hard. It was such a power trip standing there fucking Hannah’s mouth. Then I went a little too deep and caused her to gag slightly and then cough so I stopped.
“Sorry about that,” I said feeling bad.
“I’m ok. I’ve gotta work on my gag reflex,” Hannah joked.
We got back in our seats and I dealt us two more cards. We counted to three and turned them over. She had a 8 and I had a 7.
“Hmmm,” she said, pondering, “I’m so bad at this I’m not sure what to say.”
“Do you want to officially lose your virginity?” I asked.
“No… well… not officially,” she replied.
“What do you mean?” I responded in genuine curiousity.
“Well… do you remember the kind of porn I told you I liked?” Hannah asked.
I scanned my memory for a moment and then I remembered the conversation we had a few days earlier.
“Oooooh I see,” I said as it dawned on me, “You think you’re ready for that?”
“Absolutely,” Hannah said emphatically.
“Ok,” I said enthusiastically, “I have a condom but I don’t have lube.”
“I have some,” Hannah said as she hurried into her bedroom.
A moment later she returned and handed me the bottle of lube.
“Have you ever handled a condom?” I asked.
“Nope,” she answered plainly.
“Here… I’ll show you how they work,”
I opened the wrapper and handed her the condom and walked her through putting it on me and rolling it down the base of my shaft. I was still fully fucking hard at that moment.
“Where should we do this?” Hannah asked.
I surveyed the room for a moment and keyed in on her couch which had a tall, padded armrest.
“Over here,” I indicated as I took her hand and walked her to the couch, “I’m going to start very slowly, ok? Tell me if I’m hurting you in any way.”
“I will,” she agreed.
I instructed her to bend over the couch. I stood up behind her and gave her ass a gentle smack. I then ran my hand along her pussy lips and teased her clit again for a moment. Then I stood up straight and moved closer to her. I spread her ass cheeks apart and ran my finger around her tight little asshole. I then put a little bit of lube on my finger and started massaging Hannah’s asshole. After a about 30 seconds I gently inserted the tip of my finger. I started pushing my finger tip in and out of her slowly. Then I progressively inserted my finger deeper and deeper as she adjusted.
“Do you like that?” I asked her.
“Yes,” Hannah whispered as she looked back at me over her shoulder.
“Are you ready for my cock to be in your ass?” I asked in an authoritative tone
“Yes… please fuck my ass,” Hannah replied in desperation.
I squeezed some lube into my hand and rub it all over my cock. Then I squeezed some more and rubbed it all over her ass. I edged up close to her and pressed the head of my cock against her.
“Do you want it?” I asked as I teased her ass with my cock.
“Fuck yes. Fuck my ass, please! I need your cock in my ass,” Hannah begged.
I pushed my hips forward and inserted the tip of my cock in her ass. My size is average but even with average size I know it’s best to go slowly.
“Oh fuck,” Hannah gasped.
I added some more lube as I started sliding just the first inch of my cock slowly in and out of Hannah’s ass.
“Fuck that feels so fucking good,” Hannah whispered.
As she acclimated, I started gently going deeper. After a while the full length of my cock was inside Hannah’s ass. As I withdrew I added more lube for each new thrust into her. It became easier and easier and I gradually started going faster. Before long I was fucking her ass without any reservation.
“Do you like that, Hannah?” I asked as I penetrated her deeply.
“Fuck. Yes. I. Do,” she answered in a stunted manner with each thrust I made into her.
“Good girl. Take my dick,” I said feeling bold in the moment.
“Call me a slut,” Hannah insisted.
“Yeah? You like that you little slut?” I asked, “Are you a slut for my cock?”
“Oh God, yes! Fuck my ass like the little slut I am!” she screamed as I pounded her from behind, “I love that big fucking cock in my ass.”
Her dirty talk really turned me on and started to send me over the edge. I push her shoulders down and started fucking her really hard and fast while I smacked her ass pink.
“Oh fuck. I think I’m going to cum soon,” I warned her.
“Oh fuck yes. Do you want to cum on my face?” Hannah offered.
“Oh my God, yes!” I exclaimed.
I pulled my cock out of Hannah’s ass and quickly discarded the condom. Hannah turned around and dropped to her knees next to the couch.
“Come on, baby. Cum all over my face,” Hannah commanded while I stood there stroking my cock.
“Of fuck. I’m gonna cum. I’m gonna cum!” I warned her as I leaned my hips forward to position my cock right in front of her face.
I felt a wave come over my body as my cock spasmed and shot warm streams of cum all over Hannah’s face. She flinched at the first to hit her face and started laughing.
“Aw fuck that feels so fucking good,” I said as my whole body quaked in release, “You are so fucking hot.”
Hannah sat crouched and laughing at the absurdity of the moment, one of her eyes closed to protect from my cum.
“Can you get me a paper towel or something?” Hannah laughed.
I scurried into the kitchen and got her a paper towel. Hannah wiped herself off and we both went and fell onto the couch exhausted.
Hannah eventually explained that since we weren’t boyfriend and girlfriend she wanted to save her vaginal virginity for something serious. We both confided how we just really needed this. I needed to get my mind off of Natalie and stop wallowing in constant depression. I felt isolated and alone and that is something Hannah and I shared. Hannah had felt very lonely living in a new area and was building a bit of a complex in her head between her lack of sexual experience and her body image issues. She said she felt comfortable and unreserved with me and that comfort gave her the confidence to try things she would be too timid to attempt with a serious romantic partner.
Hannah and I would make nights like this a regular occurrence for the next year or so. We treated each other like our own personal sex dolls with which we could experiment but I never fucked her pussy.
Source: reddit.com/r/gonewildstories/comments/ybwl17/virgin_friend_becomes_a_friend_with_benefits_mf
Amazing story, really enjoyed it