Losing my Anal Virginity to Nichole

Literotic asexstories – Losing my Anal Virginity to Nichole by SluttyMatthew,SluttyMatthew
Losing My Anal Virginity To Nichole

This is a transcript of my experience with Nichole that occurred in June, 2023. The last time I had seen Nichole in person I had given several of her shemale friends each a blowjob (which we all loved) but more importantly, Nichole had revealed to me that she wanted to have anal sex with me. And as I resisted she had introduced me to using a butt plug for her (which was a profound experience for me).

Nichole had instructed me to wear the butt plug every single day and wear it longer and longer each successive day. The butt plug got me sexually aroused so I did not mind. I had learned to wear the butt plug for four hours straight with no problem. And although I was still unwilling to allow Nichole to fuck me, I DID think about it as Nichole instructed. Every time I felt that filled up feeling from the butt plug deep inside of me I mentally thought, “this is what Nichole’s cock is going to feel like when I finally let her fuck me.” And Nichole strengthened this by routinely texting me, telling me to put my butt plug in and asking me,

“Matt, how does that butt plug feel inside you?”

And I would respond,

“Nichole, I love this feeling of your cock inside me.””

And one day in June Nichole texted me (AND Latisha) this message,

“Matt, I want you to wear your butt plug for 2 straight hours, three times a day every single day for a full week. And while you are doing this, I do not want you to cum at all, even once. I texted Latisha too as she will be watching you closely to ensure that you do not cum all week long. Trust me, it will be worth the effort.”

And Latisha DID watch me closely and I did NOT cum (although I would have if I could have gotten away from Latisha long enough). And after a week of having a butt plug inside of me maintaining my sexual arousal through anal penetration and NOT being allowed to cum, I was VERY horny.

That was when Nichole had me and Latisha come over to her house promising a surprise for me. I was thrilled as Nichole had promised to buy me more butt plugs and an anal dildo. Before we were about to leave Latisha got a text and I got a text at the same time. The text was the same and instructed Latisha to put my butt plug inside me right before we went to Nichole’s place. This thrilled Latisha and since Nichole had asked, I let Latisha put the plug inside me. Then we went to Nichole’s.

When we reached Nichole’s, Nichole asked me right off if I was willing to let her fuck me. I told her I was still unwilling to do so. Nichole responded, “That is what I figured you would say so I got you a bigger butt plug and a dildo. Matt, another use for butt plugs is preparation for anal sex. We WILL have anal sex so I am going to get you used to it now. Latisha, show him what you brought.”

Latisha reached into her purse and pulled out her strap-on harness and a realistic dildo of hers which I recognized (it was almost 2 inches wide and a little more than 6 1/2 inches long). She put the harness on quite quickly and attached the dildo so it hung down from her body like a real cock.

Nichole went on, “Matt, you may not be ready for actual real anal sex but you will soon want to try to see what the feeling of actual anal penetration feels like. You will train for this further by allowing Latisha to fuck you with her strap-on dildos. If you are aroused by the feeling of the butt plug deep inside of you then you will like Latisha’s cock inside you even more. Hold on…”

As Nichole went into another room Latisha stood behind me, rubbed her cock between my crotch and said, “Matty, I can’t wait to fuck that tight ass!!” I had mixed feelings and said nothing. Nichole came back with a big bag and some baby oil and some lotion and a towel. Nichole took a new butt plug out of the bag which WAS larger, roughly 61/2 inches insertable and 2 1/2 inches thick. Nichole ordered me to drop my pants and underwear. Nichole said, “Take the butt plug you have in out. We will have you try this larger butt plug. We must train you to use larger butt plugs to prepare you for the strap-on dildo that Latisha will soon use on you.”

I slid the butt plug out and Nichole oiled the larger butt plug up and slowly and gently slid it inside me. It took several attempts but Nichole finally slid it fully inside of me! The effect of the larger butt plug was electrifying! The sexual arousal was more significant from the very start! It was so huge inside of me!

Nichole noticed this right away so took advantage of my arousal to explain. “Matt, there are many reasons for using successively larger butt plugs on you. You are turned on I can tell (and I WAS actually more turned on by the larger size). Since you are not yet willing to let me fuck you… you need a little help accepting the idea. Consistently increasing the size of the butt plugs you will be wearing will mentally condition you from physically being a sexual penetrator to physically being a sexual receiver. Very rarely do you experience any sexual satisfaction with us shemales but soon your sexual satisfaction will be derived from strap-on dildos and my cock instead. And when it does, the increasing sizes of the butt plugs will assist in accommodating larger size cocks. So it is important that we use larger butt plugs to cause your erogenous zone to shift from your cock to your ass. Why don’t you walk around a little before I explain another reason why we will be using larger butt plugs on you.”

I said nothing but walked around as Nichole asked of me. The feeling of the larger plug inside me felt amazing. All I could think of was, “Oh my god this feels so hot… it feels like there is a huge cock inside me! Nichole is right! The larger size of this butt plug is turning me on more!”

Nichole knew exactly what I felt and said, “Does the larger size of this butt plug result in a stronger sexual arousal?” I responded, “Yes.” It feels like a large cock inside you doesn’t it, Matt,” she asked. “Yes,” I answered again. “That is what I hoped for Matt.”

She explained, “See, don’t be scared by this but using larger and larger butt plugs on you will result in a gentle feminization of your sexuality. The more you use the plugs and the larger plugs you use, the more aware you will become of being sexually aroused by being anally penetrated. This will result in you eventually becoming accustomed to the feeling of a cock inside you like a girl. This gradual feminization of your sexual awareness will eventually result in a strong desire to be actively anally penetrated.”

Nichole paused and Latisha watched and I said nothing as I felt the huge butt plug inside of me and wondered if Nichole was right after all. So she went on.

“I know you do not believe this but, especially with how I tell you to masturbate with the dildo I will give you, the more you continue to use the butt plugs, the longer you use them each day, and the bigger butt plugs you use, the more you will like the feeling of your ass filled up by a cock-shaped object. Trust me Matt, there will come a day where you will CRAVE the feeling of a cock in your ass!”

“But I do not want to be fucked like a girl,” was all I could manage to blurt out.

“Don’t worry Matt… you will still like girls just like you do now. You will just learn to appreciate what it is like to feel like a girl sexually. In fact, eventually, when you allow me to fuck you regularly you may even cum like a girl too just from being fucked. But in between then and the time when you first allow me to fuck you, you will experience another feeling which girls feel. You will not allow me to fuck you and wearing the butt plugs arouses you but you will not be able to cum from either yet. Your inability to cum from being fucked will develop in you a hot, lusty, frustrated feeling which we girls get when we cannot get laid. But don’t worry about that now. Just feel that big cock-shaped plug inside you for now.”

For about 45 minutes we talked and drank as Nichole talked about how enjoyable anal sex can be and Latisha listened and constantly stroked her big strap-on dildo and smiled at me. And when someone needed a fresh drink, I was always asked to get up and go to the kitchen and get the drink so I could further experience the feeling of the butt plug inside me. I will confess the feeling of being anally penetrated made me quite horny.

Finally Nichole announced, “You look really horny Matt. Why put off ’til tomorrow what we can accomplish today, right? Why don’t you go into the bathroom, take the butt plug out for now, go to the bathroom and shower so you are completely clean. I have something else to show you.” Latisha just smiled her silly sly smile while holding her strap-on dildo in her hand. So I did what Nichole asked, went to the bathroom, gently slid the new butt plug out of me, went to the bathroom, then showered and cleaned the plug and myself thoroughly. When I re-entered the room, Nichole now had two dildos with her, one of medium thickness and another of larger thickness. Nichole told me, “Matt, these are for you to masturbate with. You will soon find out that you like anal sex and you will be glad I gave these to you. I will show you how you should use them. From now on, when you jerk off, I want you to use these dildos at the same time. Here, come with me into the other bathroom.”

Clad only in a towel, I followed Nichole who carried the two dildos into the other bathroom and Latisha, still sporting her strap-on dildo, followed me. Nichole asked me to kneel on the linoleum facing the bathtub so my kneecaps were flush against the side of the tub. Then she asked me to spread my legs a little wider and slowly sit down until my ass was completely against the tiles between my spread out legs with my calves fully on the ground. Nichole gave me a little push forward to ensure my knees were directly pressed against the tub then she stood back and eye-balled my position for a few seconds. Then she licked the suction cup of the smaller dildo and firmly pressed the suction cup end of the dildo directly to the linoleum 12 inches to the right of my butt so the dildo now stood straight up in the air like a hard cock. Then Nichole said, “Okay! That looks good! Let’s get that cock hard Matt! Stand up and lose the towel!”

As Nichole took a bottle of baby oil off of the bathroom counter and unscrewed the top, I dropped my towel. Nichole got on her knees and started to suck my soft cock with her wonderful lips. As I got harder and harder she took a generous amount of baby oil and spread it all over the dildo stuck on the tile stopping her impromptu blowjob only long enough to say, “Make sure that you use plenty of lube on your dildo.” Then she went back to work sucking my cock.

But when my cock reached its fully hard state Nichole stopped blowing me and stood up, placed a little baby oil in my hand and ordered me to start slowly stroking my cock as if I were jerking off. This I did despite my confusion. Nichole sat down on the floor near the tub and to the right of the dildo stuck to the tile and watched for a little then said, “Good! Now, I want to see you straddle this dildo so when you are stroking your cock you are also riding this cock inside you. Get down on your knees again, one knee on each side of the dildo and the dildo behind you. I knelt as she asked me to with her help. Then Nichole advised me, “Okay, hold onto the side of the tub with one of your hands for leverage.” This I did. “Now, reach behind you with your other free hand and find your dildo.” This I did. “Position the head of your dildo so it is under your ass and hold the head steady as you position your body until the head of the dildo is pressing against your asshole at a comfortable angle.” This took a little bit of time but I told her I was ready after about 20 seconds. “Now, just slowly lower your body onto the dildo a little tiny bit then rise back up off of the dildo. Then lower your body onto the dildo once again but lower yourself a tiny bit more so the dildo goes a tiny bit deeper then rise fully off of the dildo again. And keep repeating this process slowly going deeper and deeper each time.” And I did it! Going slowly and with Nichole’s help and encouragement I got all 6 inches of the dildo inside of me. Soon Nichole had me riding on the dildo as I was stroking my cock. The feeling of a cock sliding in and out of me which I was controlling was thrilling. Still, Nichole made me stop the experience and stand up before I came.

Nichole, while looking at me, handed the baby oil to Latisha (who was now standing) as she said, “Matt, now you know how to masturbate with the dildos and I expect you to try jerking off with these dildos inside of you when you cum as often as you can now. You seemed to enjoy it. Now bend over the bathroom counter and spread your legs a little wider.” As Nichole was stilled clothed I figured she was not planning on fucking me but I still asked, “Why?”

Nichole grabbed my hand, pulled me to the counter, turned me around to face the counter, and gently but forcefully bent me over at the waist until my right ear and right cheek were against the marble of the bathroom counter. She leaned in close to me holding her right hand firmly on the middle of my back and whispered in my ear, “Matt, you learned that riding a dildo is not too bad of an experience. But you should feel what it is like to be fucked too. It is Latisha’s turn now so relax.”

I felt another hand also pressing on my back to hold me down further and another hand spreading my ass wider as I felt a dildo pressing against my ass while I heard Latisha exclaim, “Matt, it is time to learn what it feels like to be fucked by a cock!”

I was a little scared as I felt Latisha’s cock slide a little bit inside of me, slide a little bit out, then slide even deeper. It took Latisha no more than 20 seconds to get all of her dildo inside of me as I gasped! Then she started to slowly stroke it in and out of me. It stung a tiny bit and felt weird but as Nichole continued to encourage me to relax and try to enjoy the feeling, and Latisha continued to stroke the full 6 1/2 inches of her dildo slowly in and out of me, the pain went away, and the feeling became almost enjoyable until I was surprised to realize that my cock had begun to swell!

I felt both of Latisha’s hand’s now move to my ass cheeks as she moaned a pleasing, “mmmmmmm,” sound. As she stroked in and out of me she would, every now and then make a moaning sound of pleasure like ‘ahhhh’ or ‘uhhhmmmmm’ or ‘ohhhh yeah’. I was still kind of shocked that I was being fucked in the ass by a cock-shaped object and it did not feel terrible. Occasionally, I too would let out an ‘ohhh’ sound when I felt a little uncomfortable but this was not too often. Suddenly Latisha changed rhythm and, worked the whole cock inside me in one swift stroke as deep as she could and she would moan with each deep fuck she gave me. I knew she was getting turned on when she began to increase her speed a little. Then she pulled her dildo out of me, put one of her legs up on the counter to gain leverage, put her dildo back inside me and fucked me some more. After a minute she stopped, pulled out of me again and stated, “I need to fuck that ass even better. Lie on the floor on your back with your legs in the air.” This I tentatively did but when I was on my back, Latisha lowered her whole body over me, entered me once again and started to fuck me quicker. Then she started to stroke my hard cock with a free hand teasing me, “you like my cock inside you don’t you, Matty!” I was beginning to realize that I was getting very aroused and felt like I might cum soon so when Nichole approached Latisha from behind, touched her shoulder, then whispered something in Latisha’s ear which caused Latisha to not only stop fucking me but to pull out of me altogether and stand up, I was disappointed and somewhat shocked.

Nichole took my hand and helped me up and the three of us left the bathroom and went to the living room. I sat on the couch and Nichole sat on my right. Latisha sat in one of the chairs. As I sat there naked, totally hard, and so horny, in desperate need of cumming, and somewhat confused, I became further confused as Nichole began to remove all of her clothing revealing her glorious, semi-hard cock. Once fully nude Nichole turned to face me, widened her legs, and sat down on her calves while holding up her body from behind by placing her hands against the armrest. Her semi-hard cock was directly beneath my face when she said, “You have done very well so far today Matt with the dildos and the strap-on. You deserve a treat. So I am going to let you suck my cock. But as you are sucking my cock I want you to be constantly thinking of how a cock inside your ass now arouses you,” and Nichole slipped one of her butt plugs inside me. The plug she used was only a little over 2 inches thick but it was 7 inches of insertable length and every moment after it was in me I felt it deep inside of me. It made me aroused. It made me want to cum so badly. It made me think of cock every time I felt it. So as soon as it was in me, I felt I needed Nichole’s cock in my mouth and in my throat! I bent over her and swallowed as much of her cock as I could right away!

Now, my memory of what happened next was somewhat disjointed. The only reason that I am able to delineate my experience in such detail is because, later that night I found out that Latisha, in typical fashion, had filmed all of the action with her cell phone. The rest of this story is based on the video she shot that night.

As you know by now I love sucking Nichole’s beautiful cock and am pretty adept at deepthroating so I went right to work sucking 6 inches of her hard cock in and out of my throat as Nichole knelt completely stationary before me. The only sound that anyone heard was the noise the opening of my throat made each time I took Nichole’s cock slightly into my throat:

{gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}…

After about 45 seconds of this I decided I was ready so on the next up-stroke, I took a deep breath and slowly swallowed 6 inches of Nichole’s now fully hard cock into my mouth. Then I pushed and forced her cock even deeper until every inch of Nichole’s 8 inch cock was in my throat. The first three inches of Nichole’s 2 inch thick cock had now passed the opening of my throat. The feeling of her thick cock stretching my throat from the inside was so amazing that I stopped and left Nichole’s cock fully in my throat for a few seconds as I marveled at the feeling.

Nichole must have loved the feeling as well because, when I finally bobbed off of her cock, she no longer remained stationary but rocked her body back and forth so her cock slid in and out of my throat at a fast pace. Nichole was getting turned on so when she said, “Suck that cock, Baby,” I got down on my stomach and looked up as she began to face-fuck me at a reasonable but constant rate without stopping. This non-stop face-cucking caused the typical deepthroat sounds but also caused me to gag occasionally and drip saliva onto the couch cushion when I gasped for a breath.

{gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… ULP!.. {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… ACK… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}… {gluk}…

Right then Nichole said to me, “Good boy,” then she whispered something else to me which I did not understand due to the deepthroat sounds I was making. It was only when Latisha and I watched her cellphone video for the first time later that night when we realized that Nichole had told me, “Good Boy. I am going to fill your ass with this big cock just like I am filling your mouth!”

I continued to enjoy Nichole’s cock in and out of my throat for about another minute when Nichole pulled her cock out of my mouth and told me to get on my back which I did. Nichole grabbed another larger butt plug from her purse, then bent my legs back and apart. Then she slowly removed the butt plug that had been in me all along. Now I had not cum in a long time and was crazy horny. The butt plug inside me had kept me aroused and thinking of cock so sucking Nichole’s dick had just made me hornier and left my cock fully hard. So when Nichole removed the butt plug (which was the source of my constant sexual arousal) I really wanted her to put it back inside me so I could stay turned on!

Nichole leaned on top of me very close. I could feel her big, hard cock against my stomach and her tits against my chest. She held the new, thicker butt plug in front of my face and said, “I’ll bet your ass is craving this isn’t it? Is it hungry for some dick?”

I wanted to feel the big butt plug inside me so I answered quickly, “Yes!” Nichole ordered me to roll over on my stomach which I did. I heard Nichole say, “I know you want to have this inside of you,” as she spread my legs apart slightly. I prepared to experience the widening feeling of a large butt plug stretching my ass as it slid inside of me. But what I got was completely unexpected. As Nichole said, “Ohhhh you are so tight. You are so fucking tight,” I felt the head of what could only be her hard 8 inch cock sliding inside of me!!!

Nichole pulled the head of her cock out of me, spread my ass cheeks, spit into my asshole (for lubricant), then slipped her cock inside me again, slowly until all 8 inches were in my ass. “Oh fuck… you feel so nice. So tight,” she moaned. As Nichole started to very slowly stroke her cock in and out of me, I was so shocked I did not know what to do or what to feel. Nichole must have been enjoying herself because, with every stroke of her cock sliding into me she would moan in appreciation,

“Uh… uh… oh… yeah… oh… yes…”

I was still in shock but her cock was so big and so thick inside me and her real cock felt 100 times better than a dildo! I guess Nichole realized I was getting used to it as she said, “You like making me feel good don’t you?” I said nothing as she continued to stroke her cock fully inside me slowly but the more she worked her cock inside me, the less I worried about my being fucked in the ass and the more I began to tolerate and suddenly enjoy the feeling. So when I inadvertently let out a little moan Nichole said,

“That’s it… uh… uh… yeah Baby… you know what to do. That’s so nice and tight Baby.” Then she began to speed up a little with faster strokes. Nichole kept making her little moaning sounds but as she did so with each stroke inside me, I began to realize that I was not only enjoying the feeling of being fucked by a real cock but that I was getting aroused more and more. I had fought against allowing Nichole to fuck me for so long. I kept telling myself that it was wrong for a man to enjoy the feeling of getting fucked by a real cock and that I should NOT be enjoying this. But the more Nichole fucked me, the more mixed up I felt. And when Nichole stopped fucking me and stayed still with her cock inside me I felt as if I should tell her something like I did not want to do this.

But it was too late. Nichole leaned even further into me and placed both hands firmly on my back to hold me in place. Then she started to fuck all 8 inches of her huge cock in and out of me at a fast pace over and over and over. “Oh yea you make me feel so good,” she moaned. “Yeah… uh… oh… uh… fuck yea… yeah… take it… oh… yes.” Then she started to spank my ass between strokes. “You love that don’t you,” she teased. “You love this big cock inside you, don’t you?”

“Is that deep enough,” she asked. “Is that deep enough for you? Can you feel my cock in your tummy?” She continued to fuck me hard and deep. I had lost all control. I wanted to cum and I started to stroke my cock as she fucked me. I was so aroused. I loved the deep anal penetration from a real cock. I wanted her to cum in me so badly I said, “Fuck me Nichole!”

Nichole slowed down and readjusted her cock and re-entered me and said, “Oh yes… right there. You get me so fucking horny.” And she started to pound me with firm, deep strokes. I begged her again to fuck me as I stroked my cock while Nichole pounded her cock deep inside me over and over again while constantly moaning, “Fuck yeah… fuck… that’s right… make me cum… do you like milking my big dick?”

“I’m cumminggggg,” I moaned and shot load after load of cum beneath me onto the cushion as Nichole continued to pound me and moan herself, “Uh… uh… uh… fuck… uh… uh… uh… oh you love this cock… uh… uh… fuck…” Then I realized that Nichole was going to cum also. But I did not care as Nichole continued to fuck me and moan, “uh…. yes… oh my god Baby… take that cock… yes… fuck me… yes… yes… oh my god… I’m going to cum! I’M GONNA CUM! OHHHHHHHHHHHHHH!”

Nichole slammed all 8 inches of her fat 2 inch thick cock as deep as she could force it to go and moaned with each cumload she shot into me, “Uh… Uh… Uh… Uh… Uh…” The feeling of her huge cock all the way inside my body stretching me out coupled with the feeling of cum shooting into me again and again was amazing! I knew right then that I WOULD be taking more shemale cock inside me now that I knew what it was like.

Nichole caught her breath as she remained completely inside of me. She kissed me then whispered to me, “Do you know what you need now?” I shook my head ‘no’ as I had no clue. Nichole responded in a whisper, “You need to get fucked by more shemale cock… but FIRST…” Nichole quickly jumped up and grabbed the larger butt plug she coerced me with earlier and as she gently slid the butt plug inside me she declared, “First, I think we will plug your ass so you can hold all of my shemale cum inside you as you feel this big butt plug inside you reminding you that you now like being fucked.”

As Latisha and I left Nichole’s place that night, Nichole texted me while I was in the car,

“I am so glad that you finally allowed me to fuck you. And even more happy that you enjoyed it so. We will fuck more in the future. But it has been a while since you sucked shemale cock. Next time you come over we can talk and I will introduce you to two new friends of mine, Laura and Fiona. Since you like deepthroating cock you will definitely like Laura. Not only is she beautiful but her cock is bigger than mine. In fact she is bigger than Lana! We will have fun and we will take you to a gloryhole. Talk soon.”

Even Latisha made it a point to tell me that now that she has fucked my ass with her strap-on dildo that I should expect to be doing it again for her on occasion. And I do not mind. Truthfully, I loved getting fucked by Nichole’s big cock. I want her to do it much more often. So much so that I kept Nichole’s butt plug inside of me for hours after I got home so every time I felt that feeling of a cock anally penetrating me I thought of Nichole’s cum still being held deep inside me. I may even let some of her friends fuck me.

We’ll see. Time to get my dildo and practice.