Jill and I continued our friends with benefits during the first term of my junior year. She was very adventurous and assertive in bed.
We had used the dildo and vibrator on several occasions, taking turns fucking each other. She really loved giving it to me with that the dildo, going so far as to hold it against her pussy and fuck me from behind with it like a man. That was incredibly fucking hot…feeling her hold onto my hip with one hand and slamming me with her “cock”. Another time, I added the vibrator to my clit while she fucked me and I’m damn certain my screaming woke the dormitory.
We had some amazing times together exploring our own sexualities and pushing our limits in trying new things. My former RA, LeeAnne, and I had done similar but it was less adventurous even though we were together longer. She was the one who first slipped her finger into my ass. I remember the sensation and the shock as to what she was doing to me. And I also remember it was the start of my anal adoration. While LeeAnne may have introduced anal play to me, it was Jill who first fucked me in that tightest hole. Jill relished rough play, she was very much an alpha lover. Which was fine with me as I am generally submissive by nature.
The night Jill took my ass for the first time, we had been out drinking with some of her basketball teammates. Several of the girls knew we were sleeping together and so we allowed ourselves a good amount of flirting and PDA. We were leaning against a bar in a joint downtown getting beers for the group and I felt Jill’s hand slide down the back of my jeans and into my panties. I glanced up at her smirking and she whispered into my ear that she had plans for me later. Hmmm. I gave her a look as she winked at me and walked off.
By the time we got back to my room, she was all over me. Teasing me, grabbing me. I was hot and ready for whatever she wanted to give me. I had no clue. None at all what was in store. We locked the door behind us and Jill had my jacket and top off in seconds, sucking my freed tits fiercely. I could tell she was going to be rough with me. I pulled her shirt over her head as she sucked my tits, and expertly undid her bra clasp. We stumbled to my bed, frantically sucking and kissing one another. Pulling back, she tugged my jeans and boots off. Then she dove into my thong covered pussy with her mouth. Eating me through the fabric. Fuck she was hot to go.
I was already soaked from the flirting and foreplay. She sucked my swollen lips, pulling each free to the side of the material. Leaving my clit to rub against it as she licked and tugged and sucked me. Her fingers latched onto my thong and pulled it off quickly as she stood to remove her remaining clothes.
Her long legs straddled my face, dropping her cunt directly onto my tongue. I slid right into her hole and began to thrust. Lapping a bit and then tongue fucking her as she ground her pussy up and down on my face. She loved loved loved to ride my mouth. I would eat and eat her over and over to orgasm with no choice because she would just ride me until she was exhausted. It was fucking amazing. She only took one orgasm that way that night but it was hard and her body shook from the pleasure my tongue gave her.
When she was done, she flipped me over onto my knees. Now keep in mind, I was pretty damn tipsy from the drinking we had done. Tipsy for me equals luscious slut who has basically no limits. I felt her tongue start to lap at my cunt. Up and down, over and over. My head dropped to the pillow, my arms sinking to my elbows. Relishing the licking she was giving me. I was ready for her to fuck me, as had become her favorite last time.
I heard my drawer open and confirmed yes. She was going to rail me. Yes. I mean fuck yes. I loved when she fucked me like a man. Holding me from behind. Thrusting into me. It was incredible. Jill had another plan that night. I felt the coolness of the dildo against my body. The head pressing against me. Pushing forward to slide into me. But it wasn’t my cunt it was pushing into. I felt the tip against my ass, leaning into me. Pressing hard against the resistant hole.
Wtf??? No. This was not going to happen. A tiny slender lady finger was one thing. A dildo. I mean a cock sized dildo was a FUCK no. But why did it feel so good? That pressure. That tiny stretch as she slid it forward ever so slightly. God. I couldn’t breathe. I didn’t want to do it. But I did. I wanted her to fuck my tight ass. Would I still be a virgin there if she did? It wasn’t a real dick, right. I didn’t care. And quite frankly, I wanted it once she started.
Jill pushed forward. Holding my back with one hand, her “cock” in the other. Inching it into me slowly. Lubing me with her spit. It hurt. I mean it fucking hurt. And it wasn’t big. Maybe an inch wide and 5″ long. I cried out at one point to stop because it became too much. Jill pulled it back, I heard a bottle and knew she was putting my bedside cream on the dildo. And then she wiped some on my ass.
I caught my breath and waited. Waited for her to just do it. She moved behind me into the fucking position. The dildo pressed against her body like a man. She pushed into me. It slid easier this time and sank in several inches. I cried out but it wasn’t in pain. Fuck it felt amazing. Her body began to move with the dildo in me. In and out. Slowly at first. Allowing my body to adjust to the intrusion.
I reached between my legs and could feel my pussy covered in my cum. I was so slick. So dripping onto my bed. My ass stretched open, taking every inch of that dildo until I could feel her skin on mine. Jesus. And then she fucked me. Her body moved against mine, firmly and in a steady rhythm. I rubbed my clit quickly. I wasn’t going to last like this. She was hitting me in parts I didn’t know existed with her girl cock. My head started to spin as her fucking continued. Slamming her cock as deep into my ass as it would go. I came for her. My ass clinching down onto that rubber cock as my fingers rubbed quickly and felt my orgasm coat them.
My body collapsed and I begged Jill to pull it out, I couldn’t take anymore of it. She retreated and lay the dildo on the nightstand. Crawling up the bed and wrapping her body around mine, we passed out. Exhausted from the fucking and the booze. We woke hours later and went at each other again. Slowly. Taking our time. My ass was so sore and I couldn’t take anymore that night. But it wasn’t the only time she took me like that.
Source: reddit.com/r/gonewildstories/comments/xrak2u/ff_my_first_anal