Oh, Sherry!
by Mushroom
Copyright© 2022 by Mushroom
Romantic Sex Story: A retired porn actress decides to give an interview describing how she entered the industry and what things were like years ago when she started. But things do not quite go as expected, and she lets slip more than she had expected.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft Fa/Fa Drunk/Drugged Lesbian BiSexual Heterosexual Historical Group Sex Interracial Black Male White Female Cream Pie Oral Sex Pregnancy Prostitution .
You want to know how I got started in my career? Well, there is nothing much to tell, really. I was 18, and had just graduated. And trust me, I never set out to be the “Meg Ryan of Porn” as one reviewer claimed I was. I grew up in Canoga Park, went to Canoga High. Got my cherry popped at 16, in my boyfriend’s bedroom one day after school. We had gotten stoned, and I had jacked him off a few times. But for some reason I got really horny, and let him do me.
Thankfully I got my period a few weeks later, last time we did it until I was on the pill. Then we did it a lot, until his mom came home early and caught us in the act. No shit, on the floor in their living room. Called me a tramp and forbid him from seeing me again. Oh, we still got it on, but not as often as before.
Skateboarding? Oh, I started that when I was 10. It was really big back then, I even have a picture of me somewhere when I was that age. Pink dress and my hair in pigtails on my Makaha. Makaha? Oh, you don’t hear much about them anymore, but they were one of the first to use Cadillac Trucks. It was urethane, a pretty blue. Yes, urethane was big in skateboards in the 70’s, most of us used them.
Well, I got serious about it when I was 16 and they built a skate park near the High School. After I broke up with Brad, I started going there all the time. Started smoking too, as well as puffing. By the time I was 17 I wanted a car, but my mom could not afford it so I started saving up my own money. I even turned a few tricks, even back then.
My first time doing that? Well, I had gone to a skate park in Reseda. It was a different crowd, and even scored two joints for letting one of the guys feel my boobies behind the restroom. It was about five miles from home so I skated to Sherman Way to take the bus home. I was sitting on the bench when this car pulled up and asked me if I was looking for a ride. I thought nothing of it, and when I said I was going to Canoga Park he said to hop in.
I had hitched rides before, it was not a big deal. He offered me a drink so he took us through the drive-through and drove us to a park. It was just getting dark, and I think he was surprised I was only 17. That did not stop him from asking if I wanted to make $40. And when I asked doing what, I was not surprised when he asked for a blowjob.
And I decided, what the hell? I had blown guys for less reason than that, so once I finished my burger I had him pull it out and bent over his lap. Thankfully it only took about five minutes, but it must have been a while as the load he blew in my mouth was huge. And I did not know I should have gotten the money first, but he did pay me. He even gave me $50!
And that was the first time I got paid for sex. A few months later I turned 18, and finally told my mom to go to hell and got this radical hair job. I dyed it black from my natural brown, and kinda shaved the sides like Cyndi Lauper. You don’t remember? Well, it was past my shoulders in length, but I shaved the sides to just stubble. And at the same time I started dancing at The Bat Cave. Yes, that’s the name now, but it was Bat Cave back then. They changed the name every year or so, because they kept getting sued. But they started it as a bikini bar when the TV show was big, and kept the look.
Oh, it was a titty bar by then, topless in bikini panties as they served beer. And I was kinda punk looking, and was young so the guys loved me. Good night, I could make $100. But I was still taking the bus all the time. One time, I even took my board on the stage and wanted to do some tricks. What a mistake that was, got me fired! I did not realize how slick the stage was, and when the board landed it slid right out from under me!
I landed on my ass, and the board went sailing into the audience. Thankfully it did not hit anybody, and my ass hurt like crazy. The owner came out of his office and screamed at me to get off the stage. He took me to the back and told me to get out, I was done. Thankfully one of the customers had grabbed my board, and when I left 20 minutes later he was waiting for me and handed it to me.
And that was how I met Rocco. We talked for a bit, we smoked up a bit, then he offered me $50 for a blowjob. I had done this several times over the past few months, and he was nice enough to save my board. So we drove to this apartment he had nearby, which I later learned he only used for shoots. He had a nice cock, and he really made me work for it. Having my look up at his face as I was sucking him, move down to lick his balls, things like that. And a first for me, he had me jack him off as he came on my face.
He drove me home, but gave me his card when we got there. I was shocked he was a producer of porn. But he promised me more money than I was making at Bat Cave, and I needed the work and money. Two weeks later I had my first shoot. It was one of his usual ones of that time, he had yet to move up to the classy stuff he does now. And it was just like my first time. I would wait at a bus stop, and a guy would pull up and give me a ride. We then went to this apartment he had in the area and I gave him a ride. It took about three hours to shoot, and I made $500.
In the next three months I did about half a dozen like that. I even went to his house once where he was having a party, a bunch of Russian businessmen and there were five of us there as entertainment. I swear each of them fucked me at least twice, and my mouth and pussy were sore by the time I passed out in a guest room. But that was over $1,000, so I knew I would be getting my car soon.
The next week we had finished a shoot and he asked me to stay there once everybody left. Now this was not unusual, and he was a good lay and always paid me a bit more for doing that. But he handed me a beer and asked me if there were things I would not do. Well, I told him right away I would not take it in the ass. I would also not do more than two guys at once. No pain, no handcuffs or shit like that, and no humiliation.
I still remember him looking at me, and asked if that was against me, or against others. I said either, I was just not into kinky shit like that. He sighed and said that was too bad, as with my look I would make a good dominatrix. He then asked me if I did girls.
Now of course I had kissed girls before, what teen had not done at least a little experimentation like that? But that was all, just the kinds of things we do at 14. Maybe feeling the sides of each other’s boobs a bit before we broke away in a fit of giggles. I said I had not done that, and was not interested in it. He sighed and shook his head, and actually drove me home without sticking it in me.
The next week I was at a porn shop, as my first tape was finally out. Rocco said he would send me a copy, but I wanted to see what it looked like. And there it was, “Bus Girls”, and I was the star! It was two hours, and had four of us in it. This was still early in the “Pro-Am” industry, and by today’s standards it was quite crude. Just two camcorders like you would get at a department store, editing done with two VCRs. And most of us girls came and went.
Oh, I had some dreams of breaking into “real porn”, the kind that was actually shot on film. But even then that was dying, the home market replacing the Pussycat Theaters even then. You know that movie a year or so back, with that guy from that rap song a few years ago? Yeah, the end of the movie was about that era. The older star that my mom loved was even kinda like Rocco, but he drove around in a limousine where Rocco’s had him driving an old Vega. Oh, Rocco even then had a Porsche, but used this lime green Chevy for the videos.
Well, I also looked at some of the other videos, and was surprised. A few of the girls I recognized from that orgy party, and some were rather kinky. One even had nothing but a girl jacking off guys. As in, lots and lots of guys. Kind of the reverse of what Rocco was doing. And after my next shoot I asked Rocco if I could do one of those.
He looked at me, and shook his head no! “Sorry Sherry, but that is kind of an exclusive deal I have with Holly. She does all of those videos, she actually owns part of that. But tell you what, she is starting to include other girls, would you like to do one of those?” I nodded, as that did sound kinda fun.
Well, what I did not expect was that a week later, he asked me again if I would do one. I said yes, and asked how many guys we would be doing. “Oh, you don’t understand. This is not with guys. We have done six of those, and all have been selling good. No, Holly talked me into a series of her fingering girls. The first one went on sale last week, and we have already sold over ten thousand copies. So we are about to do another one, and I think you and her would be great together. I gave her your first tape, and she really likes you.”
So I said “Sorry Rocco, I don’t do girls. If you want one with me and her jacking off guys, I can do that. But I ain’t feeling up no pussy, I love cock.” But he laughed, and said I did not have to even touch her. “No, this is her feeling up the girls, not a real lesbian feature. We set it up like the others, she meets you somewhere. Then coaxes you somewhere private, and fingers you to an orgasm. You don’t have to even touch her, unless you want to that is. At most, all she expects is a hug at the end and nothing else. The first one was really sexy, and all of the girls loved it.”
He coaxed me a bit more, but when he offered me $750 I decided to go for it. There was a car lot I often skated past that had a green Datsun 210 that was just over $2,000 and that would finally let me afford it. I pushed his pants down and sat on his cock and rode him hard and fast as my way of thanks, but my eyes were of me in a car. And trying to not think of what I would have to do to get it.
The next week in the middle of the week Rocco and I had decided on how it would be set up. I would wear some loose tan shorts and a loose black shirt with a punk band on it. We would meet at a little used skate park in Northridge and do it there.
They filmed about 20 minutes of me skating and doing some tricks, and I saw Holly sitting on a bench nearby. She was a little bitty thing, about six inches shorter than I was. And her tits were fucking huge! But she did have a great smile, and looked cute. Finally we were ready, and Rocco had me move to the bench and take a seat and complain I had pulled a muscle.
And right away, her voice captivated me. She sounded younger than she was, and her voice was not really high, as much as sultry. She complemented me on my skateboarding, and asked me how long I had been doing it. We talked for about twenty minutes on skating, and she really did seem interested. And when she offered to massage my “pulled muscle”, I almost said no but remembered that is what I was there for.
And oh boy, did she have gentle hands. She really was giving me a massage, but was a bit teasing also. Letting her pinkie go a bit closer to my groin than was really needed to massage my thigh. Then when she asked if I could lie down to make it easier, I found myself nodding. And that was when we found ourselves in the bushes nearby.
And holy hell, then she really started the massage. And even though I was telling myself this was only for the money and I was not into girls at all, there was something about her touch that was actually getting me excited. And I even blushed when she leaned almost to my ear and softly said that I was obviously enjoying it also, as my nipples had gotten hard.
And they sure were! And when she slipped her fingers inside the leg of my shorts and rubbed me through my panties, I was so fucking wet. And unlike a guy, she took her time. Teasing me through my panties, caressing and rubbing as she softly told me how exciting she found me as she watched me skate. Then slipping my panties to the side and rubbing my pussy directly.
I had been felt up by a lot of guys by then, but none had ever done it so tenderly. I had even had some lessons from Rocco and other gals on how to fake an orgasm for the camera, and I expected this would be the same. After all, nobody watching those could tell if we came or not, we were not important. It was all about getting the guys to cum.
Well, I knew as soon as I felt her fingers slip into me that she wanted me to cum. Not cum for the camera, but to cum for real. To cum for her. And within a few minutes I was doing just that. Only my second real orgasm on camera, and it was for another girl!
I expected her to stop, but she kept going. After my second orgasm she pulled her hand out, and after opening my shorts slipped it down the front. And she kept making me cum, over and over again. And by that time she was resting her head on my shoulder, her body pressed against my side and occasionally giving my neck soft kisses. Even whispering encouragements as I whimpered and said I was about to cum yet again.
It was like I could not stop cumming. One after another, it was like one would end and she was soon building me up for another one. And after whispering over and over and slowing her fingers each time, I finally nodded and told her to go ahead.
And I shuddered as she used her other hand to push up my shirt and revealed the thin black bra I had on under it. Which she also just pushed up as it was for looks more than support and took my nipple into her mouth. And with that little girl who was a few years older than I was sucking on my nipple I came yet again. And after I finished I whimpered for her to stop, I was so sensitive.
Fuck, in just an hour I had more orgasms than I could count. Later she told me it was at least six, and that is about right. The video only showed two of them, but Rocco admitted a lot of that ended up not being used at all. She had to help me stand, my legs did not even want to work right. And then she gave me a hug, and I hugged her back and we kissed each other’s cheeks as I gave a wave and headed off.
And once Rocco called cut, the two guys with us that were helping do the shoot applauded as did the others. I know I was blushing like crazy, but Holly gave me a big hug and said I was fantastic. She then looked down, and said I could not go home like that.
I looked down, and holy shit! The tan of my shorts was now dark and wet at the crotch! I had gotten so wet it was obvious I had either peed myself, or had been doing things I should not be doing. She told one of the guys to go get me some something to wear, I could not leave like that. He protested there were no other clothes in the van and Rocco told him to then go buy some. He handed the guy some money as Holly led me to one of the bathrooms.
The other cameraman stood guard outside as we went in so I could get cleaned up. She held my arm as I slipped off my shorts and panties, and they really were soaked. As was the inside of my thighs half way down to my knees. She looked into my eyes and smiled, and said it was obvious that I had enjoyed myself. And I admitted that I had, even though I had not expected it.
“Holly, I’m not into girls. I mean, at all. I only did this for the money, and was only hoping I would not be completely repulsed and able to go through with it.” And when she asked me what had happened, I had to admit that her touch was so unlike what I had experienced before. “I mean, it was like you really wanted me to cum. And not just doing a performance for the camera.”
“Oh, I did want you to cum. You see, that is one of the things I enjoy most about this business. I really do like when I give somebody an orgasm, it just makes me tingle all over. Inside and out.” She gave the naughtiest giggle at that, and had me sit on the sink. “I admit, I’m a bit of a slut. But I really do enjoy it when I know I got my partner off. And I could tell you were so nervous, this was really your first time with another girl?”
I told her I had been doing porn for a few months, but she really was the first girl I had ever been with in my life. As I was telling her that, she had pulled some napkins out of her purse and was wetting them under the sink next to me. And I expected her to hand them to me, and was a bit surprised when she got on her knees and started to very gently wipe my inner thighs starting at my knees. I looked down at her doing this, and saw she was looking up into my face. And I was so fucking wet and excited, I could feel her breath on my pussy. I was still throbbing down there, and could even see her nostrils open as she took in a deep breath, obviously smelling my excitement.
And I found myself giving a slight nod. That must have been all the signal she needed, as Holly leaned forward and gave the most amazingly gentle lick from the bottom of my lips to my clit. Never once taking her eyes off of mine. Then she did it again, and I found my hand leaving the sink and coming to rest on the back of her head as I pulled her in.
Now I had been eaten out before, but nothing like this! Most times it was a “lick and a promise”, mostly to make sure I am good and wet before they stick it in. But this was so different, it was obvious she was enjoying herself, and wanting me to enjoy it as well. And for about ten minutes she ate my well fingered pussy until I came. I had to bite my hand to keep my moans quiet it felt so fucking good! I did not even care that the cold metal of the sink was uncomfortable under my ass, a girl was eating me out! And making me cum!
Finally she did help wipe my pussy up, so it was no longer so obvious what we had been doing. Then the guy came back and she went and grabbed a bag from him, and inside was some sweat shorts. They were really big, but with one of those strings at the waist so I could pull it in so they did not fall off. And when Holly kissed me before we went out, I could taste myself on her lips. And even found myself kissing her back.
My mind was in turmoil as I said goodbye to everybody and headed to the bus stop. I mean, I just knew I was a straight girl. I absolutely loved cock! I loved when a guy fucked me, even if it was just for money. Even if I did not cum, it just felt so fucking good as they pushed themselves in and out of my pussy. I loved holding their cocks, I loved sucking on their cocks. I loved cocks, but why had I enjoyed the touch of that girl?
And I was already planning on calling Brad when I got home. He only lived a few blocks away, so I could skate to his house, get stoned, and he could fuck me crazy and remind me how much I loved cock. But I was a bit surprised when a red Mustang pulled up next to the bus stop. I was thinking this might be some guy asking if I wanted to make some money, and I was all for it. I had cum more than ever before in such a short amount of time, and was still horny.
But I was surprised when the window went down, and it was Holly. She asked what I was doing, and I told her I traveled around the city by bus. She shook her head and offered to give me a ride home. I was a bit nervous, but went ahead and got in. And when she asked me my plans now, I said I finally had enough to get a Datsun I had my eye on. And was going to get ahold of a friend to toke up a bit.
She then said she had a lid of good Columbian at home and asked if I wanted to share it with her. And I found myself saying yes, even though I knew where that might lead us. Well, she lived in a decent apartment in Pacoima, and I was a bit surprised that she lived with a man. Gary was slender, and really cute. When we got there he was about to make some hotdogs so the three of us sat in the kitchen and ate, then he said he had to take off. He smiled at me and gave Holly a kiss then headed off.
“Wow, your boyfriend’s really cute!” I said. And he was, with his long brown feathered hair. But I was a bit surprised when she laughed, and said he was not her boyfriend. “Oh, Gary is in the industry also, and I have worked with him a few times. But let’s just say that other than working, he bats entirely for the other team. In fact, his preferred position is as catcher.”
She giggled as she went into the bedroom, and I sat on the couch slightly stunned. Hell, Gary was a bit “Preppy” looking for my taste but I still would not kick him out of bed. But he was gay, and did porn also? That was a bit of a shock.
But at that Holly came out and said “Ta-da!”, holding a bong in one hand, and a baggie in the other. And we sat on the couch and got baked. And after only a few minutes she insisted I call her “Linda”.
“Holly Wood is my screen name, but at least when not on the set you should use my real one.” We talked about a lot of things, like how we each got started in the industry. Turns out she was actually engaged, but the guy left her to go to another country and expected her to wait for him to return. For three years! So she got another boyfriend, and soon another career.
And one I knew she was doing quite well in, as when I had been at the porn store I saw dozens of covers with her face on them. She had been doing this for about 3 years, starting when most were still done on film. She even opened a cabinet by the TV, and inside must have been over a hundred videotapes. She pointed out that the ones on top were Gary’s, and those on the bottom were hers.
I got on my knees and looked, and I recognized a lot of them. I held one out and she gave kind of a sad smile, saying that had been one of her first movies, with her ex-girlfriend. She had got Linda into the industry, then cast her aside when she thought she was rising faster than Linda was. “Hell, she even pretended she was a real actress. And that my hooking on the side was beneath me. But I don’t fool myself, all of us in these are basically getting paid for sex. She will only do it in front of a camera, but I got no problem getting paid to fuck in a hotel room also.”
I admitted I had done that also, even before I got into porn. “What can I say? I am a bit of a slut, and love dick. I do not go walking the streets looking for guys, but if one asks and he looks good, why not go for it?”
I had looked through most of her videos, and one of them surprised me. “Anal Virgins: First Time Anal”? And her face was the main one on the cover. I held it out, and she laughed. “Oh yes, my last feature as the original Holly Wood. I did not really want to do it, but he paid me enough to get these bigger implants.”
I looked at them, then at the cover and actually felt a little sad. I thought she looked great, but did not want to hurt her feelings by saying her implants now looked really really bad. I said that was something I would never do, and she nodded. “It’s not for everybody, I had resisted for a long time but I needed the money. Offers were drying up, and I had hoped it would get me back in the A list.”
“Did it work?”
She sighed, and after taking another long hit she passed the bong back and shook her head. “Nope, my agent said I had ruined my ‘girl next door’ looks, and pretty much all the offers stopped dead. Then I got into a bad relationship. Gary saved me, and is the one that got me hooked up with Rocco.”
I asked her how that had come about, and she described meeting him here in the apartment, then her pitching her idea for a series featuring handjobs. First demonstrating her abilities on Gary, then on Rocco himself. And by the time he left, they had a handshake deal on the series and ownership.
I told her about his picking me up after a bad night on stage, and my sucking his cock. She smiled, and said that was like him. “Rocco likes getting new girls, and tries to turn the sex into an audition. So yes, he was actually directing you, as if you were being filmed. And he must have liked what he saw, as you work for him now.”
We both had a hell of a buzz on, and sat on the couch and talked for hours. And as she got on the phone and ordered a pizza, I admitted that I was surprised she had not hit on me at all. “Sherry, I hope you do not think that was the only reason why I invited you over. Would I like to get with you again? Hell yes! However, I like you as a person also, and know you are not into girls. In fact, if you were to stay the night and asked me to just cuddle with you, I would do just that.”
I leaned back and looked at her, and she nodded. “OK, are you asking me to spend the night, Linda?”
“Sure, why not call home and say you are having a sleepover? We can have some pizza, watch some movies, smoke a few more bowls or have some beers. And I promise, I will not push you. However, if you do sleep with me do not be surprised if I cuddle with you, or move my hands in my sleep.”
We both giggled, and I said I could handle that. Then called my mom and told her I was staying with a friend. “Sure you are, it’s Brad, right?”
I got a bit pissed, and yelled out for Linda to say hello. She yelled out “Hi Sherry’s mom!”, then giggled. And it did sound like she was still in her teens when she did that. Well, my mom actually apologized then! That was a first, and I said I would see her when I got home.
Well, she asked me what movie I wanted to watch, so as we ate she started the first of her videos with Rocco. And wow, that was something! She did six different guys, but only jacked them off. The one I recognized as the guy at the shoot with the microphone was even one of them, and he had one of the longest cocks I had ever seen!
I asked her what had started that, and she sighed a bit wistfully. “Well, I started when I was in Junior High, actually. And after a bit, got to be known as the ‘Handjob Queen’. In fact, even then it was almost like hooking. Take me to a movie or arcade, I would jack them off. I really loved it, it felt so sexy and made me feel powerful. In fact, that was how I met my old boyfriend. We were together for 4 years, then he left. Last time I saw him was a disaster. I have no idea how, but somehow he learned what I was doing and threw it back at me. Said that nobody would want anything to do with me, but that I could probably do good if I made a series of ‘Handjob Queen’ videos.”
She was quiet as she said that, and looked really sad. I went over and hugged her, and she held me tight and sobbed a bit. “Well, the last laugh’s on him. I have gone and done just that, and actually make more than when I was in film.”
“Really, you make that much? I normally clear $500 a shoot.”
She brushed her fingers though my hair, and smiled. “Sherry, that’s because you are a girl for hire. Rocco and others like him thrive on the new girls like you. You all come and go, he gets you cheap and then moves on. I clear about $1,000 a day, but I also make more. Remember, I am part owner of that series so get a percentage of the profits.”
“And he really gives that to you?”
“Oh yes, he does. Rocco may be a sleaze, but he’s an honest sleaze. If you let him, he will use you up in six months to a year, then cast you aside and never look back. But he is not a cheat or crook, other than on his wife. But if you want, maybe I can help you to be a bit more than what you are now.”
And then I was surprised when she took me into the bedroom. It had a large walk-in closet, and half of it was her clothing. She selected out this dress that was frilly and had a lace fringe, a dark pink mostly. I shook my head, but she nodded and told me to put it on. Thankfully our bodies were close to the same size, other than height and her boobs. It was too short, but it fit me decently. She then took me into the bathroom and spent about 20 minutes putting on some makeup.
Then had me take several poses as she used a Polaroid camera to take some pictures. And even I was surprised when I saw them afterwards. “There, see? Now the punk skater girl is a good look now, as you are new and fresh. But trust me, that will limit what you can do. But I can see you like this. Grow out your hair, start to dress a bit more like a college student or young working girl, and I bet you can move on to do other things.”
I hugged her, and we spent another hour going through her clothes. And boy oh boy, did she have a lot! And she made me promise to set aside some of what I was getting today and letting her help me get a new wardrobe.
“In fact, let’s get you a wig. That way you can try the new look on Rocco as your hair grows out a bit.”
“But why, Linda? If as you said I am only going to be one of his bus stop girls?”
“Sherry, you can be much more than that. Between you and me, Rocco I think is getting tired of those four girl compilation videos he is doing and wants to move to something a bit more mainstream porn. Stories, scripts, real dialogue. Half his crew have actually been to film school and they want to do more also. I hope to pitch one to him soon, and if he bites you can be in it. Maybe a secretary or something like that. But I already saw you have some improv skills, and can act a lot better than most of those he gets. I see something in you, and I see a shy little girl hiding behind that tough girl look you present.”
I looked at her and she nodded. “Trust me, I know all about putting on a face for the world to see, and hiding the real you behind it. I have been doing it all my life. Moving to porn let me do that and make money at it also. But now, no more pretending. Like you, I’m a slut. I love cock, I love fucking. And I get paid to fuck, so it’s pretty good.”
I then sighed, and said I felt the same. “But, like, I liked what we did also. Like, am I really a lesbian?”
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