Part 1 [here](https://www.reddit.com/r/gonewildstories/comments/8ubl4l/mm_losing_my_virginity_story_of_my_first_summer/)
Part 2 [here](https://www.reddit.com/r/gonewildstories/comments/8umb3d/mm_losing_my_virginity_story_of_my_first_summer/)
I guess we both fell asleep shortly after he pulled me close. I woke up maybe an hour later, he was nuzzled behind me – my nightshirt slightly pulled up and his fingers were inside the back side of my g-string! I wondered what he had been doing while I was asleep but I really didn’t care. I felt cute, sexy, wanted. I could hear him behind me, breathing. I needed to get up and pee so I gently slipped away from him and went to the bathroom. I sat down to pee, it just seemed right and I cleaned up a little.
When I walked back into the bedroom he was awake, sitting up with his massive cock rock hard again. I looked at him and smiled.
“Ready for more already? I could use another round of cum in my throat!” I said.
“Yes I’m ready for more, but you’re not going to swallow this time! Remember the video? I want to do that with you.” Bill replied.
I was stunned…I remembered the video – the tranny getting analized brutally. But i wanted it. I wanted his huge member inside of me, filling me full until he was happy.
“I think I’m ready” I said, the words barely leaving my mouth.
He told me to lay down on the bed and he’d get me all ready to go. I laid down as he requested of me. He started by kissing me on the mouth – my first guy kiss!! We let our tongues play around a bit, I put my hand down and started stroking his cock as we were kissing. He was so hard already, he felt bigger than he did before. His hand made its way down my nightgown, under my gown and into my panties. I thought he was going to grab and play with my stiffening cock but he moved right past it and started rubbing my asshole. It felt amazing – my cock was instantly hard and bumped into his wrist as he started to rub my hole, making little circles with his finger.
We stopped kissing but he left his hand down on my hole. He kissed his way down my body, kissing the nightgown until he pulled it up and started sucking on my nipples.
“I love your little budding breasts” he said between kissing and sucking on my hard nipples. I loved that he called them breasts. I decided to take it a bit further with the wordplay. I thought back to the video and remembered what they said to each other.
“Stick your finger in my pussy baby, she’s ready for you” I said.
He complied and gently spread open my tight asshole with his index finger. I moaned with excitement, it hurt just a little but it felt amazing. This was different than any toy or tampon I had put up there – he was able to move it in and out and around and I loved it. I’ll be honest, I was starting to get wet down there. I’m not sure if he had spit on his finger or what but I could hear the wetness and I could feel it as well.
“I’m going to get you nice and ready and relaxed. I want to put a couple more fingers into your cunt and eat you out” Bill said. He had stopped kissing my nipples at this point and was kissing his way down to my cock. He pulled my panties to the side and my cock sprung out, hard and at attention. The head was soaked in precum and there was a noticeable wet spot in my panties.
“Oh my god! Look how hard and wet your little clit is baby! Can I suck on it?” Bill exclaimed.
I nodded my head yes. He had called it a clit, just like in the movie. He put the head of my cock in his mouth and started sucking it. I was so horny that I knew I was going to cum soon. I warned him and he told me it was ok, he wanted me to squirt in his mouth.
While he was sucking me he slipped an extra finger in my pussy. I shrieked a little because it surprised me and hurt a tiny bit but it quickly felt good. He was sliding his fingers in and out while making a ‘come here’ motion with them to rub against my prostate. Needless to say it didn’t take long for me to blow a load in his mouth. It was a huge load, I felt like I came for 10 seconds. He didn’t swallow this time though, he pulled his fingers out of me and kept the cum in his mouth.
Then he reached down and pulled my panties all the way off. He spread my legs some and grabbed a pillow to put under my hips. He still hadn’t swallowed or spoken and I was wondering what he was doing as he started to move his mouth down to my ass-pussy. Was he going to eat me out or rim me? With my cum in his mouth? Before I could even ponder an answer I felt his lips against my wet hole, he gently stuck his tongue in, opening me up as he pushed the cum and spit out of his mouth into my ass! It felt so good! I had done an enema before and I loved the full feeling I got from it but this was something different.
Bill kept going at my hole with his tongue and lips – really working my tight cunt. His hands were on my thighs, pulling them apart to get room for his head. He was going to town down there and it felt amazing. I was so wet from all the cum and spit and I knew it was a mess down there. But the good thing is that I was loosening up quite a bit. He wasn’t having to try too hard to get his tongue deep inside of me. After a couple of minutes he stopped and got up off the bed, going towards the nightstand.
“Get naked” Bill said with authority. I only had my nightgown and stockings on at this point so I pulled off the gown. I reached down to pull off my stockings but Bill stopped me.
“Leave those on. In fact, put these back on – cover up that clit.” Bill said as he threw my panties back at me.
I did what I was told and put my panties back on. Bill opened his nightstand and pulled out a bottle of lube, astroglide. He opened the lid and squirted some on his cock, motioning me to help him rub it in. I used my hands and I started to stroke his dick, pulling back the foreskin and making sure to get him nice and lubed. His head was already very wet with precum and i spent extra time working it in near his piercing.
Without much warning he grabbed my hips and swung them towards the edge of the bed. He moved the pillow with me, just to get my hips high enough to match his hips. He looked me in the eyes and without breaking his gaze reached down and pulled the g-string to the side, exposing my hole. He grabbed the lube and squirted more into his hand, gently reaching down and lubing up my pussy. Eventually he got three fingers inside of me, getting me good and lubed inside and out.
“Are you ready baby, can I take your virginity?” Bill asked.
I couldn’t do much more than nod and weakly say yes. I was so horny, so ready for this.
I wish I could say I had imagined this moment for my whole life but I really hadn’t. I didn’t know that so much of this existed and I honestly never thought I would be with a man.
Bill grabbed my ankles with his hands, raising them up to his shoulders. He put the head of his dick right at my hole. He reached down and pulled back his foreskin – I could feel the metal of his piercing at my entrance. Looking me in the eye he gently started pushing.
“Push like you’re trying to poop.” Bill said. “It’ll make it easier for me to get in.”
I did as I was told, worried about pushing the cum and lube out. As soon as I started to push the head of his cock make its way inside of me. It burned and hurt. Bill knew. He stopped right where he was and told me to relax, it will go away in a second. And he was right! Within about 5 seconds the pain was gone. His head was now inside of me!
Gathering up some courage I said “Fuck me Bill. Push it inside me and fill me full of your cum!!”
Bill did as i asked, slowly pushing himself deeper and deeper inside of my hole. He told me how tight I was and how good I felt. He said so many kind words while he was working his huge cock inside of me. He called me his pretty little girl, his little cum slut. Told me how good I looked on his cock, with my panties pulled to the side. Commented on my limp little clitty flopped to the side.
All the words felt great, I loved them. Before I knew it I had his whole girth, all 7″ inside of me.
“i’m all the way in you baby and you feel great. You’re so tight! I’m not going to last long!” Bill said when he was fully inside me.
“Fuck me Bill, please!” I moaned.
Bill started pulling out then pushing back in. He was humping me!! It felt amazing! I felt like his cock was somewhere deep inside my gut, I almost felt like I could see it if I looked at my stomach hard enough. The sensation of his head and shaft moving around my prostate felt amazing. I’ve still never felt anything like what I felt that night.
Bill kept going, in and out, really getting his rhythm. Eventually I loosened to the point that we was going fully inside and outside of my hole with each thrust. I could feel his foreskin pulling back each time he did it – I could feel the metal of his piercing as well.
I wish I knew how long this lasted but most of this part was a blur. I was in ecstasy – looking down seeing my hose clad legs on his shoulders, watching his massive dick going in and out of me, seeing my cute pink panties pulled to the side with my little cock just sitting there.
Before long Bill told me he was going to cum. I told him to fill me full, I wanted his seed. That set him off and he started furiously humping me. It started to hurt a little but in a good way – I loved it. Bill had his head back, his arms on my hips and my legs on his shoulders – he was going to town plowing me. I could feel him start to slow down a little and I knew he was close to cumming.
But then I noticed that I had a weird feeling – almost like I had to pee. I didn’t have much time to think about it before Bill screamed in pleasure. He was cumming!! Deep inside of me!! I could feel his member shaking and pumping me full of his sweet warm sperm. But with one of his last thrusts the urge to pee overcame me and I released what I thought was my bladder.
I was so embarrassed – he was fucking me and I was peeing all over him and his bed!! But I looked down and all I saw was clear whitish fluid coming out of my cock, kinda squirting all over my belly. There was so much of it!! I didn’t know it at the time but he had just made me cum from prostate stimulation!!
“Looks like your little clitty liked that and made a little squirty mess huh?” Bill said as he pulled himself from inside of me.
I nodded, unsure of what had happened or what to say. Bill sat down on the bed next to me.
“That was the tightest best hole I’ve ever had.” Bill said.
I smiled. I was glad he was happy. I was glad he liked me.
We sat and talked for a bit before we got in the shower together. After that we wound up back in his bed – this time I was wearing normal underwear.
The rest of the summer was great – I moved out of the basement I was in and I moved in with Bill. There were many more nights like we one we just had.
I have two more stories from that summer I’d like to tell if people like what I’ve written so far. Part 4 involves my first time with a girl!! Part 5 is about my first orgy.
Source: reddit.com/r/gonewildstories/comments/8uvm84/mm_losing_my_virginity_story_of_my_first_summer
I’d like to read your other stories please :)