So I was recently asked by a friend to start writing down the stories of my sexual experiences again. After doing some digging I found one of my old stories and have to admit I found myself aroused by what I read. I also remembered how much I enjoyed writing it as well as the feedback I got from readers. So here we go!
I guess I should start with a description of myself. I am in my early 30s. My natural blonde hair reaches my lower back. Green eyes, gauged ears, freckles, cute face. I am on the taller side at 5 foot 10 inches, and healthy weight at 175. My breasts are what I would describe as a handful, however they are one of the places I am noticing my Covid-19-idle-summer and unemployment weight is seeming to locate itself. I would describe my style as “metal head girlfriend”, wearing mostly black, and band shirts in varying state of decay.
So today’s story happened actually within the last few days. I have been seeing my current boyfriend for about 3 months. He checks off most qualities in men that I find attractive. Black hair, dark eyes, tattoos, good taste in music, about my height, some kind of crazy facial hair and what I like to call fat buff. We will call him Ralph for my stories. Ralph lives in an adorable little cottage nestled in an older neighborhood in our city about 3 miles from my apartment. I enjoy spending nights at his cottage as he has a nice kitchen for me to cook for him and it is much more quiet than my apartment which is right on top of a major highway. I adore him and am very much in love with him but we have yet to drop “I love you”s you eachother.
We have been having fantastic sex for a while now. I can never get enough of it, but it was always very straight forward. We make out, I start rubbing his crotch, clothes get removed, I suck on his cock while he fingers me, I get on top to ride him, I jump off just in time to suck him off and let him nut down my throat. Easy. 100% satisfied every time. The emotional connection that is there is so fulfilling for me that I don’t mind that at all.
Like so many other people right now I am not working and really struggling to fill my time. And also like a lot of people right now I find myself masturbating more and more to fill that time. I had just gotten myself off and knew I was going to be spending the night at his place that night so I started packing my overnight bag. The idea was hatched then and there I was going to spice things up a bit and bring a toy or two over to his place. I had two in mind. I have a U shaped vibrator with a remote control which I placed in a drawstring bag and a small wand vibrator I also put in the bag. Threw a few small blister packs of lube in there for good measure and tossed it in my backpack. Good to go! My plan was to get to his place, go hide in the bathroom, put the U shaped vibrator in me and then come out, hand him the remote and get to cooking dinner.
He picked me up later that afternoon and almost instantly knew I needed to rework my plan. We are both fans of major league sports and are both fixing for the returns of our favorite sports but will watch almost anything at this point. He had a motorcycle race he wanted to get back to his cottage ASAP to watch. Meaning no store for dinner stuff or me making dinner. We got to his place, ordered a pizza and got settled in to watch the race. After the pizza and the race we switched over to some bass fishing derby on tv snuggled up together. By that time he had taken off his shirt, revealing his hairy chest and belly. I had peeled off my tight black jeans to my black boy shorts and popped off my shirt so I was just in my red and black halter top sports bra. Cozy outweighs sexy in my book, however this fills both roles. I draped my right leg over his lap. He placed his left hand on my thigh. I reached over with my left hand and held his right on his chest. Cuddle pretzel. We watched the fishing show some more, cracking jokes and kissing once and awhile. I felt his hand slowly migrate in between my legs. We started kissing and he pushed his hand under my shorts and started slowly stroking my pussy lips before parting them and just lightly rubbing my vaginal opening. This teasing always gets me super wet. I reached down with my right hand and started petting his dick under his pants which he had sneakily unbuttoned by this point. We continue to kiss and I start debating what to do. Should I save the bag of tricks for another day and just keep going with our normal routine? Should I stop being shy and weird about it? This isn’t the first time I have bought stuff with me. Not even the 3rd or 4th time. I break the kiss and say “I bought a few surprises for you.”
“Oh yeah? Like what?” Ralph asked, his voice in a lower than normal rasp.
I rolled over and fished the drawstring bag out of my back pack. I pulled one of the packs of lube and opened it. I put some on my hand and then started stroking his cock. “Oh nice.” he started kissing me again. We made out for a while longer. I pulled my head back.
“That feels really nice.” Ralph said with a slight moan.
“But wait there’s more.” I said almost in a sing-songy tone.
“Really?” Ralph chuckled. Pulled my head in for another kiss. “Let’s see.” I rolled over and pulled out the small wand and handed it to him. “Ohhhh yes!” he said. I showed him how to turn it on and he pressed it into my clit. I turned my head into his chest with the sudden stimulation and pushed my hips into his arm more. We made out while he worked out where he was aiming the head of the wand while I continued stroking his dick which was now the hardness I have felt him from hand play only. I broke my head away again.
“Well there is one more thing.” He removed his hand and the wand from my crotch and perked an eyebrow. I rolled over again and pulled out the remote from the bag and handed it to him.
“What’s this for?”
“This.” I handed him the U shaped vibator.
“Oh cool! So like this side goes in you and this side…” He took it from me and started examining it.
“Can go in me too, or sit on my clit.” I chuckled.
“In your…”
“In my butt.” We have never done any kind of anal play. We haven’t ever really talked about it in a serious manner. He has what I like to call a boyfriend cock. It’s not huge. It is perfect for marathon sex becasuse it doesn’t leave me sore from either gurth or length. Since the begining I knew I wanted to have anal sex with him but was too shy to say anything and would just need to get there naturally.
I gave him a run down of how the remote worked and then put the vibrator inside of me. He pressed the pulse button and nothing happened. He pressed it again and still nothing. WTF. He tried turning it off and on again. Still nothing. Feeling embarrassed and angry at the nice sex toy I had bought for myself that was now not working, I pulled the toy back out of me and put it back in the bag. We laughed it off and I said I would mess with it later, hoping it was just the battery.
We went back to making out, this time him fingering my pussy. He was drumming his finger tips right on my g spot and so I pushed in a little on my pelvis with my hand to make it more intense. He slowly worked me up to an orgasim. Then switched his fingers attention to my asshole. We continued to kiss and I could feel my ass relaxing to his finger and then his 2nd finger. After a while I finally broke our kiss.
“I want you inside of me.”
“I want to be inside of you.”
He rolled up to his knees and got in between my legs. I took his cock in my hand, which I had put more of the lube from the blister pack on. I rubbed him and myself with the lube and then directed his head to my asshole. He slid it in without much resistance and gasped “Oh that is tight” I wrapped my legs around his body.
“I want you to dump one of your fat loads into my ass.” I pulled him closer to me and we kissed. It didn’t take very long till he was starting to make the noises I recognised as him getting close. “Fill me up with your cum baby.” We kissed again. He wrapped his arms tightly around my body.
“I’m cuming.” he let go of my body and pushed up to his knees while grabbing my hips and pushing himself as deep as he could. He collapsed on top of me, still with his cock buried in my ass. We looked deeply into eachothers eyes and then kissed. And then held each other till he became soft and slid out of me. After a while of just holding each other and kissing he went to the bathroom and bought me a damp towel. I cleaned myself up. Put my shorts back on and grabbed my undershirt to put on. We watched TV for a while, cuddled up. We started to get ready to go to sleep. I went and refilled my water bottle and slipped back into bed to find he had already gotten naked again. He normally sleeps naked. I started rubbing his thigh and before long I was once again tugging on his cock. I rolled over and grabbed the rest of the lube and went back to slowly jerking him off. His legs started twitching and I got up onto my knees and then on top of him and slowly pushed him into my pussy. He put his hands on my hips and started grinding me down on him and I rested my hands on his belly. The emotions inside me were overwhelming. We locked eyes. “I love you.” The words spilled out of my mouth. He wrapped his arms around my back and pulled me down to kiss him. We locked lips while I rose and fell on his hard cock. Not breaking the kiss he lifted me off of him and pulled out to cum in between our 2 bodies covering both our bellies with his hot seed. There was a lot more cum this time than when he came in my ass. We laid there, me on top of him, holding each other and kissing for a while longer. Sleep was coming fast for both of us. I got up and retrieved the towel from earlier and we got cleaned up.
We both drank some water and then got settled into bed. We kissed and told each other good night. He draped his arm over my hip and we both fell asleep.
The next day I went and got new batteries for the remote. It totally was the battery! I am going to try again with the cooking dinner and having him have the remote idea again later this week. Hopefully it will lead to more fun stories to recount for you all. I hope you enjoyed!
Source: reddit.com/r/gonewildstories/comments/hu4cvb/first_time_having_anal_sex_with_my_boyfriend
So sweet! Hope he eventually said “I love you” back.