Amy Tale/s – My First Anal

I went to the bathroom and just sat on the toilet like I was constipated and his cum would drip every now and then, and a little blood.

It is a Saturday morning at Ethan and Michael’s apartment. Emma and Clair are here too, where we all spent the night after a group sex session. I want to use this tale to provide a consolidated bio on my current sex circle of friends, starting with Michael, who manages a retail store in the mall where I work at another department store parttime. I flirted with Michael after I got a job there because he is a decent looking black guy about 6’ tall and average build. He has a 9” cock that I call typical thickness. I had a one-night stand with Michael at his apartment where I met his roommate Ethan, a 6’ 3” muscular black hunk with a thick 12” big black cock (they are both 28 years old), and I seduced Ethan. Both Ethan and Michael are circumcised, and they use a hair remover on their genital regions, and Ethan’s balls are smooth and a pleasure to lick.

I refer to Emma as my ebony princess and she is Ethan’s girlfriend of 3 years (she is 27 years old), and I seduced her into my lesbian lover. Her skin complexion is lighter than Ethan’s and she is 5’ 11” in height and she also uses hair remover on her body, and she is so silky soft that you must touch her skin constantly. Emma’s pussy is totally shaved, soft, and so sweet to eat. Emma is pretty and has black hair that is straight and hangs about 6” below her shoulders. She has a hot curvy body, sexy legs, hips, ass, and feet and she is big boned (not athletic, and not fat). Emma is bustier than me in the 36dd range with pretty pinkish brown nipples.

Clair is a white milf a year younger than me (we both have been turning 39 again for the past couple years), and she is a brunette and 5’ 7” in height and is a little heavier than me but curvy and sexy with a trim hairy pussy with black hair (triangular), and the lower part is shaved. Clair’s breasts are slightly bigger than mine with pink nipples. Clair is hot and has nice legs, calves, feet, and body creases. I seduced Clair into my lesbian lover too.

I am Amy, and comparable to Clair (we are both white milfs), except I am a sandy blonde and my hair extends to the middle of my back, and I am 5’ 6”+ in height. I have 34dd breasts that are soft supple and bouncy with pink nipples and a soft body with pretty toes, feet, legs, and a nice ass and hips. My pussy is trimmed with soft brown hair (triangular), and I shave the business area. I have a pretty face with small features. I do not wear any jewelry, and I almost always keep my toenails painted red. I have a small c-section scar, and it use to bother me, but everyone loves my soft tissue above the scar, and they find it sexy. My pussy looks good and I like to flash it, people also develop a fetish for my ear lobes, and an irresistible urge to rub my soft pussy hair and supple breasts, and my feet and toes, and to kiss on my thighs. There is more detail in the previous 8 tales on my current sex circle of friends.

Everyone at Ethan and Michael’s apartment is up and wearing nighties or shorts and shirts, and it is 9:30am. Clair was curious about ordering some sex toys like she had seen in our toy bags, and we were using Ethan’s computer in his room to look. The guys are watching TV in the living room, kind of. We messed around wasting time and it was close to noon. Everyone had grabbed what they could for breakfast, but we wanted some more food now.

We decided on some takeout and convinced the guys to go get it. We ate, relaxed, and it was heading toward 2pm. The girls were on the couch, and Emma started kissing on me, and she pulled my nightie off and kissed me all over. Emma told Clair to spread the blanket on the floor. Emma took her nightie off too, and she pulled me into the floor on top of her in a 69, and she ate my pussy, and I ate hers. Emma must have motioned to Clair, who was naked now too, and she got behind me and was licking my asshole as Emma ate my pussy. They got me off, but then I could hear them whispering to each other.

Clair gave Emma the lube, as she put some on my ass and Clair began to finger my asshole. Emma was still under me in a 69, and I continued to eat her pussy. Clair led Ethan to the floor on his back, and Clair got on top of him and stuck his big cock in her pussy, and she grunted and moaned as she fucked him. Me and Emma are still licking each other’s pussy, but Emma is fingering the hell out of my asshole now. I did not see this, but Clair must have given Emma the butt plug, and she started using it on my asshole.

It felt good, it was different, and then she pulled it out and I looked, and Michael was kneeling behind me. Emma had a hold of his dick, and she started guiding it into my asshole. Michael pushed and made entry and I grunted, he pushed in deeper and started thrusting some, and I was grunting, uhh, uhh, uhh, in rhythm to his strokes and feeling the pressure and I was tense. He was not all the way in. Emma squirted some more lube, and Michael began to see how deep he could go. The pressure was intense, and it hurt, but it really felt good, especially at the outer rim.

Emma went back to eating my pussy and Michael fucked me in the ass with me squealing louder as he got faster and deeper until he got off in my ass. I went to the bathroom and just sat on the toilet like I was constipated and his cum would drip every now and then, and a little blood. I got in the shower and eased the douche in my ass and rinsed it. [It took a few days for me to quit hurting from this]. I went back in the living room and everyone had finished whatever they were doing. I had enough for the day, and I dressed and gathered my stuff and left.

About a week later I came by before work and me, Ethan, and Emma hooked up for a threesome. As usual me and Emma started on each other orally and found our pleasure. I wanted Ethan’s big cock in my pussy, so he fucked me doggystyle while I was on top of Emma. He got off in me, and I enjoyed the dick throbbing of a big cock deep in my pussy, which I like. We rested for a while, until we started getting horny again and we could get Ethan hard.

Emma begged me to try Ethan’s cock in my ass. I told her that I was sore after Michael did it, and we debated, and she convinced me to at least try some of Ethan’s cock. I was on my hands and knees and Emma lubed us and fingered, then she used the plug. It was not as bad as I thought. Then Ethan started, and when he made entry it was worse than I thought. Emma kept holding me and encouraging me to take it.

Ethan went slow, and he never got more than 6 or 7 inches in, but he did not cum in my ass. We did not do it anymore that day. Since then, I have been doing it more and more, and I am now used to taking just about all of Ethan’s big cock in my ass. I did not let Michael fuck me in the ass anymore, but I am sure after Ethan, Michael would be easy.

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