My First Anal Experience
- 2 years ago
- 21
- 0
Chris's First Anal Experience free porn video
A few days after my first oral experience with a man, I decided I needed tits like a real woman. I went online to a few cross-dresser sites looking at their breast forms. There was quite a large variety. I looked through the few bras I had to see which size fit and looked best.
The 32B was cute and seemed proportional to my small frame. I ordered a pair of symmetrical forms and a pair of asymmetrical forms in a 32B size along with the medical adhesive to attach them. The confirmation noted it would take seven to ten days for delivery. I was scheduled to go to a customer the next week so the timing seemed perfect.
At the end of the week, Jim called me and asked when we could meet, again, at the bookstore. I told him I would be away for a week and wanted to meet when I got back. He gave me his phone number so I could call him upon my return. I was so excited that I packed a couple of complete feminine ensembles for my business trip. In the past, I was always afraid that somebody might find them when I traveled, but my trip to the bookstore had liberated me quite a bit and I didn’t want to be without my comfortable women’s clothes for so long.
Monday morning I flew out to the customer, loaded the new update on their computer, and spent the day checking all the new functions. It went well so I was able to go to my hotel, get checked in, and eat dinner before six. Back in my room, I immediately changed into a pair of black and red lace panties with a matching bra, a pair of tight stretch shorts and a long shirt that came down below the shorts.
It felt so good wearing them. I only wished I had the breast forms I ordered. I was getting excited thinking about them and seeing Jim.
I sat down and started surfing the internet for cross-dressing sites. There were several good ones with tutorials on make-up, hair styling, walking, talking, and dressing to look passable. As I watched, I practiced talking in a more feminine voice. Then, I got up and tried walking like a woman. I couldn’t believe how much fun I was having. When I watched one on skincare, I was convinced I would feel more feminine without the little hair I had on my arms, legs, chest, and underarms.
The next day, after work, I went to Wal-Mart and bought lipstick, make-up, nail polish, perfume, and hair remover using the self-checkout. I didn’t think anyone would notice the absence of hair since I had little hair in the first place and my legs, chest, and most of my arms were always covered at work. Back at my room, after dinner, I experimented with the make-up and lipstick in front of the mirror in the bathroom. Then, I put the hair remover on my arms, legs, and chest.
After about ten minutes, I wiped it off with a moist washcloth. The hair remover had aloe in it which made my skin feel smooth. I treated myself to a bath since the directions said to rinse well after removal. I washed my face clean of the make-up and lipstick before putting on some lingerie for the night.
I spent every night while I was away experimenting with lipstick and make-up. The last night I decided to paint my toenails. No one would see them with my shoes and socks on and the only time I was barefoot was when I was alone at night or in bed. I was amazed at how feminine I felt with the nail polish. This was going to be a regular thing from now on I thought to myself.
The next morning I flew back home. I wore a pair of panties under my casual pants on the plane. When I arrived back at my apartment, there were a couple of packages on the doorstep. I couldn’t wait to get inside and open them. It was the breast forms I ordered a week ago. I took off all of my clothes, except my panties, and put on the 32B bra.
Then, I opened the first box like a little kid at Christmas. I took out the breast forms and pushed them into my bra. It was heavenly. After a few minutes, they warmed to my body temperature and it felt like I had real tits. I opened the other box and tried them on, too. I couldn’t decide which set I like best.
There was a catalog in the second box. I sat on my bed and looked through it. That’s when I realized I didn’t have a wig. I was going to have to get back into my regular clothes so I could go out and shop for a wig. First, I had to call Jim and let him know I was back. He was as glad to hear from me as I was to call him. He suggested we meet that night since it was Saturday, the biggest and most active night at the bookstore. I told him I would be there at nine o’clock, this way it would be dark when I leave.
I put on a pair of sweat pants over my panties, took off my bra and breast forms, and put on a pullover shirt. I looked on the internet for stores to buy wigs. One of them was a market that contained multiple discount stores about fifteen minutes away. It was perfect. Most of the stores were run by foreigners who would sell anything to anybody.
The store with the wigs had women’s clothing, shoes, stockings, pocketbooks, and cheap jewelry. I told the lady working there I needed a wig for my girlfriend. She was very helpful. After a brief conversation about my imaginary girlfriend, she suggested a shoulder-length light brown straight hair wig. She picked one out, combed it, and put it in a box while I looked at some sandals.
I discovered that women’s shoes used a different size measurement than men’s. My size seven was a women’s size nine. It was a good thing I tried the shoes with my socks on; I almost forgot I had painted my toenails during the week.
Before I left, I picked out a pair of sandals, a small clutch, a pair of ladies stretch jeans, and some jewelry. I think the lady started to suspect I was shopping for myself, but she played along with me saying my girlfriend would like everything I bought. She also said I could bring anything back that didn’t fit or she didn’t like. I couldn’t wait to get home to try everything on.
As soon as I walked into my apartment, I pulled off my shirt and pants. I tried on my sandals and stretch jeans. The jeans felt and looked so good. The tag on them said they had “Tush Push” elastic in the rear. They would be perfect for tonight. Then, I sat down and read the directions on the medical adhesive spray for the breast forms. I decided to take a bath before applying them. I put bath beads that I had bought last week in the water. They made my skin soft and my whole body smell good.
Since I was going out after dark and coming home tonight, I could paint my fingernails. I used the same nail polish on my fingers as I did on my toes a few days ago. It was like Christmas lights on a Christmas tree, you couldn’t miss them.
Next, I cleaned my chest with rubbing alcohol, and then sprayed the breast forms with adhesive, letting it dry a few minutes, before pressing the asymmetrical forms to my chest. I lay on my back on the couch for ten minutes to let the adhesive set before putting on my lacy 32B bra. I was so glad I bought the breast forms and adhesive. They felt so real and natural.
It is sometimes difficult to pick out my panties. I’ve started to build quite a collection and I love every one of them. However, I found a full front thong that I had never worn for some reason and it suddenly appealed to me tonight. When I put it on I had to wonder why I never wore it before. I loved the feeling of the strap between my cheeks. I put on my new stretch tush push jeans and a thin white blouse. When I looked in the mirror I could see my bra through the blouse. It really looked sexy.
I sat in front of my dresser mirror and put on my wig. I practiced combing it in case I needed to straighten my hair when I was out. At first, I was concerned it could come off, but it stayed on when I combed or brushed it. It was time to put on my “face”. I’m glad I practiced all week when I was away as it still took me an hour.
I started with an eyebrow pencil, then eyeliner, followed by make-up. One of the tutorials demonstrated how I could make my nose look smaller using the proper shades of make-up. It worked well. I didn’t want to look like a painted lady. I just wanted to look like a lady. The final step was the lip gloss and liner. While it was the most difficult, it was the most rewarding. When I was done, I was amazed at how natural I looked.
It was already eight o’clock, so I needed to finish up. I put on my new sandals, a pair of clip-on earrings, and a bracelet. My painted toenails in the open toe sandals kept catching my eye reminding me of my new identity as a woman. I not only looked like a woman, I felt like a woman. After putting a few dabs of perfume on my neck, I also smelled like a woman. Last, but not least, I brushed my teeth, gargled, and put a breath mint in my mouth.
It was time for the moment of truth. Would I be able to step out the front door like this? Fortunately, it was still cool at night so I could wear a light jacket. But, there was no hiding my face. I put a hairbrush, make-up, lipstick, and breath mints in my clutch. I took a deep breath and thought of all the effort of getting ready.
There was no turning back. I grabbed my car keys, opened the door, and took a walk on the wild side. I was nervous, scared, and excited all at the same time as I used my best feminine form to walk to the car.
On the drive to the bookstore, I wondered if Jim would like my new look. When I pulled into the parking lot, it was almost completely full. I found a space toward the back. I called Jim on my cell phone to tell him I was here. I was so relieved when he said he would come outside to meet me. When I saw someone exit the side door, I got out of my car and stood behind it. The man who came out of the door looked around the parking lot, before walking toward me. As he got closer he said, “Chris, is that you?”
I answered, “Yes it is, Jim. What do you think?”
He responded, “Damn, I can’t believe it. You’re the hottest looking woman I’ve ever seen.” Without hesitation, he gave me a long hug, followed by a passionate kiss on my lips. He took my hand and led me to the entrance door. We walked directly to the theater door, opened it, and went in.
I asked Jim, “Don’t we have to pay first?”
“Women are always free. They attract the men. I already paid for myself when I got here and Mike, the manager, knows me anyway.”
There were several men in the hallway and the theater was full, with many men standing along the walls. As we walked around the theater, a crowd started to migrate with us. I whispered to Jim, “Why does it seem like everyone is following us?”
He replied, “Because they are. They think you’re a real woman. Couples often come in to have sex in front of an audience or the woman wants a gang bang while the man watches. Either way, these men think there’s going to be some action. Let’s walk to the other end and see what’s going on there.”
We walked back down the hallway to the other end. There was a couple on the round table in the middle of the room. The woman was sucking the man’s dick while a few men were rubbing her ass, her tits, and her pussy. Jim sat down on the only vacant couch, putting his one leg against the back while leaving his other on the floor.
He pulled me down so I was sitting between his legs with my back toward him. He wrapped his arms around me and nibbled on my neck. “You smell so good. What do you think of the show? How would you like to be the center of attraction like that someday?”
I turned my head a little to look back at Jim as I answered, “I’m not sure I’m that kind of woman. Although I must admit I do enjoy watching this immensely.” He kissed me on the cheek, and then started rubbing his hands on my breasts. I turned my head forward and tilted it back on his shoulder responding to his touch. He nibbled on my ear sending waves of ecstasy through my body.
I put my hands on top of his as he explored my body. My attention was no longer on the round table, but rather on Jim’s touch. I longed for such intimacy and he was delivering. It was closest I felt to being a woman yet.
After a few minutes, I could feel Jim’s cock hardening in his pants against my ass. I turned onto my side and began to pull his elastic waistband down. However, his legs were still apart preventing me from pulling them down enough. He pulled his leg that was along the back of the couch under me putting his foot on the floor. I finished pulling his sweat pants down letting him kick them off. I’m not sure what was more exciting: his exposed cock or being so naughty in a packed room.
Still lying on my side, I turned on to my stomach with my face in Jim’s crotch. I wrapped my two hands around his now hard dick and licked the pre-cum starting to ooze from it. I was like a baby with a bottle. I had to suck it. My tongue explored his bulging member. I put my one hand on his balls as my other continued to hold his cock.
One of his hands was on my head while the other was resting across the back of my bra. No thought was needed to push as much into my mouth as possible. A few years of watching porn introduced me to deep throating. It was the ultimate thrill in sucking dick, at least when watching. I had to try it.
Well, it wasn’t as easy as it looked on the videos. I started choking on my first few attempts. Jim said, “You'd better take it slow, baby. You’re going to choke to death.” Taking his advice, I settled for licking and sucking it.
Suddenly, I felt a hand rubbing my ass. It was too far for Jim to reach in the position in which he was sitting. I pulled my head up and looked behind me. It was a man who looked to be in his thirties. He looked back at me saying, “I’m sorry, you have such a beautiful ass, I couldn’t resist, do you want me to stop?”
I had to think about it for a few seconds. It did feel good, so I responded, “No, it's okay. But don’t try to get into my pants.” Just making that statement made me feel so hot. He immediately continued his probing of my lower body. I was beginning to understand the woman on the table being the center of attention.
As I turned my attention back to Jim, he said, “Just say the word, Chris if anything goes too far for you. I’ll make it stop.” I leaned over and kissed his hand in acknowledgment as I resumed where I left off. His dick was becoming slick from the slobber generated from my failed attempts to take him into my throat. I thought I would try, again, as my confidence was increasing and my throat was relaxing.
After a few pushes into the back of my mouth, I forced it into my throat momentarily. I could feel Jim’s excitement as he pushed his hips up and hands down in response. The repeated efforts resulted in additional trips into my throat.
Once, again, I was distracted by the activity around the lower half of my body. I could hear someone say, “Is she a woman or a T-girl?”
Someone else answered, “I’m not sure and I don’t care. I can tell you she’s hot as hell.” The hands connected to the last voice continued to explore my waist, hips, ass, and thighs with renewed vigor. I spread my legs a little to give him more access. He took the unexpected welcome and rubbed between my legs searching for a clue to my gender. My small dick was still tucked into my balls and not giving up my identity easily.
I could tell he was still confused by the way his hand continually studied the contour between my legs. He quietly said to Jim, “You’re a lucky man. Thank you for sharing her with me.” Both my body and my ego were experiencing new feelings beyond any expectations I’ve ever had.
Jim whispered down to me, “I’m going to cum soon if you keep this up.”
I answered, “Isn’t that what you want?”
He replied, “I was hoping we could take the next step tonight.”
I shyly and innocently said, “And what would that next step be?” I thought I probably knew the answer but wanted to hear it from him. I seemed to have unintentionally fallen into some role-playing scheme.
He leaned down as close as possible to my ear for privacy as he said, “I want your virgin ass. I want to make your first experience a good one so you’ll want to do it again and again, hopefully with me, but only if you want to try it.”
I had watched anal sex many times on my television and laptop, and now here. Some of my best jerking off was to anal. I thought about it often. The women seemed to enjoy it and I knew the only way I could ever be fucked, was in my ass. It would be the closest experience, sexually, to being a woman that I could get.
While I thought my first time would be in a more private setting, I was hot and horny. I didn’t want to wait. I also believed that Jim would take care of me.
I sat up next to Jim pulling myself from my other admirer. I whispered into his ear, “How can I say no to you? You’re so sweet and have taken such good care of me. Where do you want to go?”
Jim stood up, still without his pants on, took my hand, and led me to a wide padded bench along the wall. He positioned me on my stomach with my head at the one end. He climbed up on the bench behind me and pulled my stretch pants and thong down just below my ass. I could hear him ripping something open as I surmised he was putting on a condom. Suddenly, I felt something between my cheeks, followed by a cold, wet, and thick fluid being injected into my ass. I figured it was some lubricant. It was an unusual, yet pleasant feeling.
Next, I felt Jim’s hard penis moving up and down my crack until it seemed to locate my entrance. Then, came the pressure of the tip of his dick pushing against my asshole. He was pushing my cheeks apart with his hands as his dick forced its way in. At first, the entrance to my ass seemed to resist his intrusion, but after a short time and multiple pushes, his stiff cock pushed my anal ring open letting him in.
I could feel my ass slowly fill as he fed his cock into me. It was a strange, yet sensational feeling. I wanted it to keep pushing in forever as I began to imagine it winding through my body and up my throat. It ended when his pelvis was tight against my cheeks. He was sitting on top of my ass with all of his weight pinning me down on the bench. My hands were gripping the end of the bench near my head. Jim asked, “Are you okay, Chrissy?”
I loved it when he called me Chrissy. All I could do to respond was let out a soft moan. I’m sure he took that as a resounding yes since he started to swivel his hips moving his cock inside me. I was never so fulfilled, and filled, in my life. I reached a point of ecstasy that sent me over the edge with an orgasm that pushed a flood of cum between me and the padded bench.
I let out a gasp that was louder than I wanted. This drew a few spectators who quickly came over. Some of them pulled out their cocks and started jerking off.
Jim continued to gyrate on top of me as all I could do is watch the crowd gathering around us. I could see them looking at me, taking in my facial expressions. It was like a porn movie where the camera would show frequent face shots which were as exciting as the actual dick shots. Only this time, I was the face. I pursed my lips and lowered my eyelids as I began to coo.
There was some reaction from the crowd as they imagined what I was feeling. I cracked a small smile that drew a comment, “She’s loving it,” from one of the onlookers.
I was beginning to slide a little on the large puddle of my cum. It was generating a familiar smell. Jim began panting and his legs seemed to be tightening. His thrusts became more deliberate. Then he let out a groan as he held himself in a constant push up my ass. I could feel his slight throbbing inside me as I knew he was pumping his cum into his condom. He leaned down close to the back of my head as he said, “Chrissy, I hope it was as good for you as it was for me.”
I turned my head slightly, “Yes, it was everything I hoped it would be. I’m so glad it was you who took my virginity. I don’t know if this is appropriate, but you’re such a gentleman.” Jim kissed me on the back of my neck before sitting up. I could feel his dick shifting inside me as he moved back up, giving me one last thrill. It was beginning to shrink reducing my fullness. When he pulled it out, I suddenly had an empty feeling as he dismounted me.
Jim walked over toward the wall in front of me, pulled off his condom, and deposited it in the small trash can. As he walked back to me, I reached out my hand. He took it with his hand and I pulled him close to me putting his limp and cum coated dick in my mouth. It was soft and warm. I licked off the cum that I have begun to love so much.
When I was done, Jim walked around and pulled my thong and pants up. As I sat up, he retrieved his pants and some paper towels. “We better clean up the mess on the bench.” I took the towels from him and wiped the bench clean. I couldn’t believe I came so much. As I walked to the trash can I realized how sticky I was in the front of my thong. My ass was also wet from the lubrication.
I felt so naughty as I moved about with my best feminine walk. Jim put on his pants before he hugged me from behind and asked, “Do you want to take a walk to the other side and see what’s going on?”
I said, “Okay,” as I offered him my hand. I was still in a state of bliss as he led me down the hallway like we were a couple and he was showing me off. In the dim light I could see my painted toenails as I walked with a sexy sway. Several men turned our way as we entered the theatre end. There were no empty seats side by side, so we stood behind the main seating area leaning forward against the half wall separating the lounge area from the theatre seats.
As we talked quietly, watching the big screen, my ass was being rubbed and touched by various men passing by. Though no longer a virgin, I still felt some vulnerability and was beginning to understand why women were not as forward as men. I liked the attention, but still wanted to choose who and when. Those choices to come in my future stories…
Louise
- 11.10.2022
- 17
- 0
- Category:
- Crossdressing
