I [F22] never thought I would be into anal. My only past sex experience with my ex was him doing missionary for two minutes and taking a nap.

Last summer though, I really expanded my experiences with some FWB's I made. My intro to anal all started when my friend K [M36] would rub my anus with his thumb while doing doggy style or 69. He would always ask it felt good and I'd tell him yes while moaning some more. The sensation would be a tingling sensation throughout my whole lower area.

One night while masturbating alone with a small ribbed vibrator, I decided to put it against my anus and rubbed my clit with my hand. The tingling sensation was amazing and it made me cum a lot faster. I grabbed some lube and put it on the vibrator and went into my ass slowly. The tingling was there along with another massaging feeling along my anus. I tried with a larger dildo but the lip on the tip was too hard and hurt coming out.

I told K the next day and I was curious about more anal play. We went to an adult store and bought some training plugs. We went back to his boat he lived on in the summer. I pulled my shorts down and sat over his lap. The smallest plug went in easy and didn't really provide any sensation. The middle one felt good going in and was comfortable while in. K pulled it out and stuck a vibrating egg in my ass and worked on my clit. My legs and ass quivered as he worked on me. He tried fingering my pussy but the back of my vagina felt uncomfortable with the plug in. I told him I would try the bigger one and would eventually want to try his cock in my ass.

K surprised me with a jeweled metal butt plug in the mail a couple days later. I put it in my ass before I went off to work. I worked at a coffee shop, the plug felt good as I would walk behind the counter. During some down time I would lean my butt on the counter and move back and forth but tried not to look weird.

I didn't tell my other friend M [F24] about my anal journey. I went to her place wearing the jewel plug. I asked her if she could give me a massage as I took off my clothes. My ass is so small she immediately saw the plug shining from all the rope lights she had in her room. After she rubbed my shoulders and glutes she pulled the plug in and out. I moaned lightly as I spread my cheeks for her. She pulled the plug out all the way and tried to finger my ass, but her finger nail made it uncomfortable. She tried different vibrators on me and found a dildo which worked amazing on me. The tip was soft enough where it didn't hurt. I moved to doggy style so M could work on my clit and I came with the dildo half way in my ass. I returned the favor licking her clit and eventually us doing doggy style with her double ended dildo.

I was pretty sure I was ready for K's cock in my ass. I came over to his sailboat. He had the table and bench seats arranged to be a double bed below deck. We started off with 69, he would stick his finger in my wet pussy and use that as lube for my anus. He would rub his finger on my ass but not go in. He laid me down on my stomach, put on a condom and put a large amount of lube on it. He told me to relax and say the safe words. 'Yellow' would be for him to slow down and be more gentle. 'Red' was for him to stop. He spread my left cheek with has hand and I could feel his tip on my anus. I could feel him slowly go in, the lube helped as I felt his hard cock go in more. My anus gave the tingling sensation as he moved in and out slowly, he didn't go all the way in but slowly made his way further in. His cock was hitting my g-spot, I moaned into the cushions. I was feeling discomfort as he was going further in, I forgot the safe word and told him to not go in as far. After taking it easy with me for a while, K leaned over to a shelf and grabbed a vibrating egg. He placed it on my clit and bunched the sheets so it stayed there and continued humping me softly. I moaned harder as my ass and clit being stimulated, I came and gasped. K's cock was getting harder and I can tell he's about to cum when his cock starts pulsing. It was so nice feeling it my ass this time. He started moaning and put his head next to mine while he came. He was still able to not go in all the way and I could feel his cock pump cum out. He made sure I was okay and nothing was hurting. I told him we definitely need to do that more often.