[MF] Sundress Story Part 2 – Losing our Anal Virginities

Disclaimer: Everyone in this story is over 18

If you want to skip to the more “gone wild” part, skip down to the line.

If you want to go straight to the anal part, go to the asterisks further down

[Part 1](https://www.reddit.com/r/gonewildstories/comments/vaq6wq/mf_my_summer_with_soph_the_sundress_story_part_1/?utm_source=share&utm_medium=web2x&context=3)

Once we got home, I set out to quickly clean the house, and make a bed for myself. At this point I was unsure whether she was comfortable sleeping in the same bed as me, while we had slept together before, this was different, and we would be spending a lot more time together than one night.

“Are we sleeping in the same bed?” I asked

“Of course” She replied “I want us to cuddle every night!”

I was hoping for a positive answer, and I was happy that I got one. She was still wearing her sundress from earlier, and I sat down next to her on the couch, laying down, and putting my head on her thighs. She jokingly put she dress around my face, and I turned my face around into her, kissing her thighs. She laughed again, and raised the skirt off of my face, bending down to give me a nice long kiss.

I sat up, and we broke off, looking at each others faces, quickly bringing them together for another deep kiss. I moved my hand down to her waist, and cupped her face with my other hand, passing my fingers through her hair in the process.

She got up, saying “lets go to the beach” whispering in my ear as she added “I want you to wait some more”

I reluctantly agreed, and we got changed into our bathing suits. She wore a two piece, a simple bottom, that left little to the imagination, the black material contrasted with her pale skin. Her butt was so cute, it was perfectly round, and with every step she took it bounced up and down. She saw me looking at her, and twirled around.

“What do you think?” she asked

“It looks wonderful” I said, adding “However, you look best without anything on”

“hmm” she replied “maybe I do”

As she spun around, I saw the front of her, the top part of the two piece was a simple, albeit small bra, letting copious amounts of side boob revealed. Spotting the knot at the back when she turned around, I quietly approached her, and distracted her with one hand, slapping her bare ass, and sliding my palm against her stomach. With the other, I pulled on the string, undoing the bra and pulling it off of her. Her breasts fell out for the second time that day, and with the bra in my hand, howling with laughter I ran away from her, followed by her yelling at me as she chased me up the stairs to our room.

I quickly hid them before she came in, seeing her topless quickly made my dick hard, and as she entered I saw her eyes dart down to what was probably quite a large tent at this point in my swimming trunks.

“Where is it?” She said

“I don’t know what you are talking about” I replied

“You’re going to make me look for it are you?”

She looked around the room, slowly approaching me, until she was right in front of me. I looked down at her face, and she moved forwards more, pressing her bare chest to mine.

“This is what you want?” she smirked

I was determined not to budge, so she upped her game, stepping up to kiss me and with one of her hands, she slipped it in my swimwear. She pulled away from our kiss, her hand still down my pants and slowly worked her way down to my dick. She wrapped her fingers around my shaft, and let them stay there.

“I won’t do anything more until I have my top” she growled

I motioned with my head to a corner of the room, and she pulled her hand out of my pants, moving to the far wall. She put the bra back on and moved out of the room. I found her downstairs, and she kissed me.

“Haha, sneaky little shit” She laughed “Now I’m going to make you work for tonight, and you are going to wait all the time in the world.”

We got out of the house and made our way to the beach. She had put the dress back on over her bikini, and it waved around in the wind, this time she carefully had her hands down by her side, making sure that it didn’t lift.

As we got to the beach there weren’t many people there, it wasn’t fully holiday season yet, so families hadn’t started arriving, so we were able to find a quiet spot. We put our towels down, and I helped Soph take her dress off, taking care to run my fingers over her skin as I pulled it down off her shoulders.

“You look gorgeous”

“I know” She replied “I wonder what other people will think of these” pointing to the hickeys I had given her

“I’m sure there are some massive insects in these parts that can be blamed for that” I joked

I raced her to the water, and we quickly got in, cooling off from the beating sun. At this point I was enjoying myself in her company, and somehow wasn’t thinking too much about earlier that day. She jumped on me in the water, wrapping her legs around my waist, and we played a game of two truths and a lie. Slowly running dry of ideas, we played another game, which consisted at naming the capital of countries, and if we got it wrong the other was allowed to ask us a question of their choosing. She was brilliant at geography, and since you were only allowed to name a country that you knew the capital too, she won most of the rounds.

This was a nice ‘get to know’ each other moment, and we stayed like this for hours, talking to each other, lost in the moment. She was still wrapped around me, her arms now on my shoulders, and my hands laced together under her ass.

We finally decided to head back into town, seeing as the sun was setting, we looked around for some food, settling on a small takeaway meal and some ice cream. I had some fun drawing a little mustache on my face with the ice cream, getting her to laugh on our way back, before theatrically licking it all off. She also joined in, kissing me and taking some of the ice cream with her.

———————————————————————————————

I had spent a wonderful afternoon in her company, but as we neared home, I was reminded of our earlier escapades. Unlocking the door, and letting her pass through it first, I was thought of what we could do.

Placing the food on the counter I announced that I would be going to the shower. I stripped my trunks off in the middle of the room in front of her, and placed it in the courtyard to dry, walking myself naked to the shower.

I made a point of leaving the door unlocked, in order for her to come in if she wanted to. I turned on the shower, and pointed my head upwards, my back to the door. The feeling of getting all the sand off of me felt wonderful, and I didn’t hear the door slide open. I was surprised when felt hands on my shoulders, massaging them, I didn’t move, letting Soph work her way down my back. She kissed my skin, continuing down until my ass, at that point I was still underneath the shower head, and water trickled down around me.

She reached forward, still behind me and pressed her boobs on my back. At the same time, her hands moved around me and found my semi hard dick rising. She hadn’t taken off the sundress yet, and she turned me around, pulling me down to meet her lips, our wet faced pressed against one another.

Her hand was still around my dick, and she started pumping as we kissed more. I undid the dress, pulling it down, revealing her bikini underneath. I massaged her boobs, searching for the knot with my other hand, pulling on the strings as she continued to pump my dick.

I pushed the bra off, grabbing both of her boobs with my hands I pushed her back against the wall, my grip firmly around both of her soft breasts. She moaned a bit as I pressed into her with my hands, sensing I was going to cum soon, she pushed me back, and dropped to her knees.

She placed her face in front of my dick, pumping now with both hands and stuck her tongue out, liking my head. She placed a kiss on my tip, suddenly opening her mouth and taking my dick in her mouth, swirling her tongue. She deepthroated me, pushing further until her lips were firmly on my base, moving her head as she made gurgling sounds.

I grabbed her head and gently guided it as she bobbed up and down my dick, slurping and moaning through my dick. I let her go as I felt my cum building, and she took that cue to get rougher, almost violently sucking, passionately moving up and down my dick. The orgasm built until it reached a tipping point, I grabbed her head as I felt myself unload into her. She pushed me further into her, as I shot cum down her throat, further spurred on by her whimpering at each twitch of my cock.

She finally pulled back, flicking my head with her tongue, taking every last drop that she had, swallowing my load. She looked up at me, licking her lips, as I panted in the heat of the shower, still coming down from my high.

“Lets finish this shower and have diner, I’m starving for some food” She croaked

Her sundress was on the floor outside the shower, still dry as it had been kicked out earlier, and it was quickly joined by the rest of her outfit. We took our time in the shower, sensually passing our hands over each other, spreading the lotion over each other. After this, we stepped out the shower together, drying each other.

She passed the sundress back over her shoulders, and I slipped a fresh pair of shorts on, opting to not put a shirt on. She went upstairs and I heard her open her suitcase, unsure of what she was doing, I set the table and prepared our food. She stayed up there for a few minutes, I could hear her rustling around.

“Is everything alright” I yelled

“I’m coming, sorry!” she yelled back

I heard her come down the stairs slowly, looking back I realized she seemed to be in a bit of discomfort, but at the time I paid it no attention. We quickly had our diner, but as we moved onto dessert, I noted that she was fidgeting around a lot.

After cleaning up we moved up to our room, she once again slowly went up the stairs which I thought was weird. As she came into the room, she jumped on the bed, laid on top of me, and we kissed.

“Is everything ok?” I inquired, at this point I was a little worried about her

“Oh don’t worry, I’m fine” She said “I’ve just got a little surprise for you”

“Surprise? How so?” I asked

“That’s for you to find out” She whispered

Without letting me in on any details she kissed my face, and my neck, slowly moving down my body, making her way down my shorts. As she did, so I started to think about what the surprise could be, and looking back it should have been obvious, but I had never had an experience like this, so I wasn’t thinking about all the clues that were right in front of me.

She undid my pants and pulled them down as I lifted my hips to help her, in one swift motion she removed my underwear as well, and my limp cock flopped around. It had probably only been ten minutes since she had sucked the soul out of my cock, so I was still recovering.

Motivated by Soph’s hands and the sudden freedom from my boxers, I was back to full mast in no time. When Soph saw this she moved back up to me, and whispered a few magic words in my ear.

“I want your cum in me tonight”

Even through the haze of my horniness I was careful, having tested myself earlier that month, and I made sure that she was clean as well. She had actually been tested earlier that week.

“You did it just for me?” I chuckled

“No, just for us” she replied

With this she pulled the dress off her shoulders and sat on my stomach. Moving her legs back she lifted herself up and over my upright dick, grabbing it with one hand, and stroked it. She slowly caressed my cock until she was happy with it, and guided it towards her pussy.

Still, in her hand she moved it around her lips, teasing my tip by rubbing her juices on it. She started circling closer and closer to her pussy until she stopped at the opening. With this she took a small breath and moved her hips downwards, easily sliding into her, I felt the inside of her around my cock, and if she hadn’t given me a blowjob ten minutes before that, I would have cummed into her at the moment.

She moaned as she slid downwards, my cock slowly filling her up. I dirty talked with her, as she told me how good it felt to have my cock finally inside her, how she waited a whole week for this.

“Fuck I missed you” she moaned

“Not as much as I did” I replied

She leaned down, placing her hands on my chest, her boobs dangling over me, and she began to ride me. Moving herself up and down me she moaned, arching her head back in pleasure. She dictated the rhythm, and with each thrust I moved around a little, hitting the spots where she liked it the most. At one point she screamed loudly “Right there”, and I stopped moving around, matching her rhythm and staying in one spot trying to hit it where she liked it the most.

As she moved up and down, from time to time I would feel something hard touch my balls when she bottomed out, I once again paid it no attention. She was moaning how good it felt to have my raw dick in her, feeling my warmth in her. I felt her start to tense and guessing what was nearing I grabbed one of her boobs, twisting her nipples.

“Fuck I’m almost there” She exclaimed

I kept the same rhythm and brought my other hand to her head, grabbing her hair and pulling it as she tensed up and pushed into my chest with her hand. She trembled as she orgasmed, my dick still in her as I felt her squeeze around it, her juices flowing down my shaft and onto my balls. She let out a last moan of pleasure, collapsing on top of me, my dick still hard in her pussy.

She lay her head on chest, laying there as her chest pressed into my stomach, heaving up and down as I breathed. Placing her hands to my sides, she pushed off of me, and carefully lifted her hips upwards, letting her juices flow out of her onto my twitching cock.

************************************************************************

“Now for your surprise” and she moved upwards to my face, lifted her legs and turned around. She moved her ass towards my face, and she pressed it in my face.

“Can you feel it?” She said, turning her head back to me

I mumbled back “What?”

I was quite confused.

She put her head down, lifting her ass up, and spread her cheeks, revealing a beautiful glass plug in her ass. I was stunned, but she explained herself.

“I got this just for you” she smiled “I’ve never worn one before, but I knew that I needed to do something before you fuck my ass”

I was silent, completely and utterly surprised, I didn’t move at all, mesmerized at what was just in front of me.

“Well, what do you think? Say something!” I snapped back to reality

“You planned this, didn’t you? Making me wait, building me up all day, until you made me cum in the shower, so I wouldn’t cum when we fucked, just so that, in the end I would cum in your ass” Realization dawned on me, she had planned everything. She had completely played me, I was so predictable, and even though I knew it, I was still doing what she wanted me to do.

“You finally figured it all out” she backed away, “I’ve been waiting for this all week, ever since you slipped those fingers inside my asshole, I’ve wanted you to fuck my ass, and you get to be the first”

“You also get to be my first” I replied

She got off the bed, seeing that I was agreeing to this, and got some lube out her suitcase.

“You really brought everything didn’t you?” I laughed when I saw her get it out

“Oh absolutely, nothing is going to go wrong today” she replied

She got some lube on her hands, wrapping them around my dick, spreading it out. It was cold at first, and this made me draw in a breath. She got a copious amount on my dick, and satisfied with her work, stopped and got up. She lay down next to me, and I sat up, pulling her ass in the air with my hands.

I was quite inexperienced with any sort of toys at that point, so I opted to playing around the plug with my mouth, liking around it, and feeling its hardness against my tongue. Carefully I tried to get a grip on it, wanting to see her little hole spread open. I tentatively pulled at the start, not wanting to cause any accidental injury.

She was on all fours, and looking back underneath, she whimpered as I pulled a little harder.

“Please say something if I hurt you” I told her

She nodded, whimpering some more as I pulled harder, and I felt it slide out, slowly at first but as more of it went out, it slid out faster and faster. I finally pulled it out and heard Soph moan as it left her asshole, the ribbed edges of the plug pulling at her hole.

There it was, gaping in front of me, opening and closing as Soph tried to relax herself. She put her head up, pushing her ass higher up. I placed my hands on her ass, and brought my mouth to it, eating her, satisfied from her moaning as my tongue moved in and out of her. I quickly stopped, unsure of how long her asshole was going to stay open.

I guided my dick in between her cheeks, sliding it around her cute pink asshole, until I heard her ask me, practically begging me.

“Please, please fuck my ass”

I moved my head to her asshole, now smeared with lube, and gently pushed at first. Being as careful as I could, I pushed some more and Soph moaned through the pillow, but I didn’t manage to push through. I applied some more lube, and tried again, the tip of my cock now just about in, I pushed some more. Her asshole felt wonderful around the head of my dick, and Soph gasped as I slowly pushed further.

I was now a quarter of the way into her ass, and hearing small sounds of pleasure escape from Soph, I pushed further in. The rest was easier than the start, her ass tightly squeezing my cock. I pushed more until I was halfway in, and started to move back out.

Very slowly at first, I moved in and out, pushing more into her with every stroke. I could hear Soph whimper with pleasure with each motion, letting out smaller sounds of pain as well. I made sure that everything was okay, applied some more lube and slowly pushed further in.

As I did so, I moaned, pleasure coursing through my body. I told how her how beautiful her ass was, and how good her asshole felt, she replied by telling me to go harder. Nearing the bottoming out point, I felt her squeeze some more around my cock, tensing as I started a rhythm, sliding in and out, listening to her whimper louder. She gasped again, her back arching in pleasure.

I loved the moment, drowning in her sounds, hearing my dick slip in and out of her.

“You’ve wanted this all along haven’t you?”

“Yes, yes” she screamed in pleasure

I slapped her ass, and she flinched, doing it again, she didn’t move. I felt a now familiar feeling growing in my balls. Grabbing a fist full of her hair, I pulled her head back, lifting her back up, and with my other hand holding her against me. This position forced me to pump upwards into her, creating some more friction, but it only furthered the pleasure.

“I’m going to cum in your ass” I breathed in her ear

She squeezed her butt cheeks together, and with each motion, I saw her ass bounce against me. I held her against me with one hand, and moved the other down to in between her legs, rubbing her clit.

I was nearing ever so close to cumming, and as I continued pushing into her ass, Soph moaned loudly. This made me cum, and I pushed as far as I could into her ass, feeling the cum fill the space. I squeezed Soph against me, methodically working on her pussy, and feeling the cum in her ass, she orgasmed again. She lost control that time, and fell forwards into the mattress.

She whimpered loudly this time, bringing her head back to mine, turning to kiss me as my dick softened in her ass. I slowly pulled out, and we both looked at the cum drip out of her ass. We fell next to each other on the bed, panting from the effort, and cuddled until we fell asleep wrapped in each others arms.

I do apologize for any typos or such, feel free to point them out, as this is quite a long story I might not have caught them all.

Source: reddit.com/r/gonewildstories/comments/vbgx9b/mf_sundress_story_part_2_losing_our_anal