First Date as a Whore - Rest of the Night
by LolaPaul
Copyright© 2026 by LolaPaul
Erotica Sex Story: When we woke from our first post-coital nap, Roger half expected me to leave, and really wanted me to stay. He had some more desires, including naughty ideas, for this once-in-a-lifetime evening of his friend’s woman playing his one-time whore. Could she do what he wanted? Some thing a whore didn’t do. Secondly would she agree to keep the nastiest business a secret? It turned out that she had some naughty ideas too.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Slut Wife Swinging Analingus Cream Pie Oral Sex Prostitution .
This assumes you have read “First Date As A Whore .” This continues the night after their nap. The continuation is rather longer and much, much more...
After the Nap
After Roger ate my pussy like a fiend, kissed me like a French lover and fucked me in a flurry of long-supressed lust, we were both exhausted and fell asleep together like lovers.
I woke up first, we were perspiring and the room was warm enough that we had not been under the covers. I didn’t move, I just spent time gazing at Roger’s body while touching myself and imagining being a bad girl. Also I was being subtle seeking to arouse his resting cock using my natural perfume. These days at home the system worked about 25% of the time.
One of my thoughts was about monogamy. They say women are naturally monogamous. I agree with that in general, there is a predisposition encouraged by most societies. But I also think there is a universal exception. I believe that many women have a secret wish for a night with another man - the attraction of a strange hand, curiosity about lips, is he different as a lover, etc. - enjoying her body. Maybe it is a handsome movie star or an Olympic athlete. Maybe the one who got away or was lusted from afar. Some couples even write 5 or 10 names on a “free pass” list before they exchanged vows, allowing their spouse “hall pass privileges” with those named, should the chance ever arise.
Roger was the only “other man” I thought about that way and my man knew all about it, he had seen Roger’s fingers probing inside me, bringing pleasure to my pussy. That was a decade ago but we still had vivid memories recalling hands and lips pleasuring bodies on the dorm room beds across the room, stirring exhausted bodies to passion one last time on a Sunday evening. I enjoyed Roger and Roger’s girl Foxxy enjoyed my man Tracy. The only explicit limit was no “cock in pussy” penetration. (Well, there was also an unspoken understanding about the back doors.) Fingers could go everywhere, like when my hand stroked Roger’s cock as he taught me the perfect touch. His tongue tickled my pussy as my guy watched.
Sometimes we flipped the switch; instead of switching MF couples the guys both watched as Foxxy and I played girl-on-girl games with each other. In either case the objective was for the ones with hungry pussies to revive their flagging lovers after a long weekend of sex, so they could get it up to thrill us one more time. Jealousy is a powerful spice if used with a light touch and the right audience.
In the years between I dreamed of Roger doing more to me, things like him fucking me then sending me back across the room to my man, soiled and wanting more of the same from my man, who would then send me back. Tracy knew of and supported these dreams, he also contributed ideas like three-in-a-bed, maybe with a blindfold “to make it interesting.” He even got a toy which we agreed was a close approximation of Roger’s cock, we employed it in our private fun. Telling me that scenario always got me wet. But I never thought I would be alone in bed with Roger, playing his whore waiting for him to get hard again while Tracy was nowhere near.
I guess my attempt at chemical sex-play was working, Roger’s cock moved as it stiffened a bit. A moment after it moved he woke up. He blinked like a owl, trying to recall how I moved from his dream to his bed, then he gave me a smile that said, “I wasn’t sure if I would find you here. I thought maybe I dreamed of you again. Of maybe you left after.”
We had stayed out dancing a little later than usual. Then came the sex, which burned fast and hot during that first round. We were both exhausted so afterwards sleep was inevitable. We both lost track of how long we slept. But we still had appetites.
Roger knew our routines. It was around 10:30 and he knew my husband and I were usually in bed by 11:00, since Friday was a work day. “Is your husband coming by to pick you up soon? Do we have time for...?”
“Yes and no,” I answered. “Yes, he is coming by to pick me up ... but maybe not so soon. He mentioned you were due at his office around 10 in the morning, so we agreed that 8:30 tomorrow morning was when I would meet him in front of the hotel.” I sighed, I tried to give it a ‘forlorn’ feel. “I guess until then I have to rely on the kindness of strangers ... or maybe an old friend. I do have my husband’s blessing to be friendly ... very friendly, all night.”
“I hoped, but could not believe it possible ... I have some ideas about what we might do. I admit that sometimes I dreamed...”
“You are not the only one,” I said as I moved to take his soft cock in my mouth, savoring our rich combined flavors. I took all of his shrunken cock inside my lips, for at least for a short time before it grew. I guess that meant he liked it too. Our “overnight date” was scheduled to run “until the morning coffee,” and neither of us wanted to short-change the other. So with my mouth full I wondered what else we might do next.
He made a decision, I was still sucking him when he reached, picked up the phone and ordered room service: coconut shrimp (they are famous for it) with some fruit, Drambuie coffee and a collection of sinfully decadent (and expensive) chocolates. The kitchen normally shut down by now except for one guy. Most of the order was easy, but if we wanted the shrimp it would take 75 minutes this time at night, most of that was needed to heat the oil.
We wanted the shrimp, it was a special treat in this town, but one I had never tasted. He said I was in for a treat.
By the time he finished the call his cock had swelled beyond my ability to engulf, so I had to use my hands to keep working up his desires.
It seemed that room service was not his only aroused desire. He picked me up and carried me to the shower where we could both handle each other in all the good places.
Good Clean Fun, Until...
We had 75 minutes in the shower so we both helped the other get clean and very dirty. As I held his body against mine I assured Roger that anything I did with him was not going to ‘cross a line’ with my husband, he knew where I was and what I was doing because he had set up this date. Then I gave Roger a very hot kiss while running my hand down his crack to run a fingernail lightly over his balls. He returned the kisses with great passion. Then he began to nibble my breasts. I said I was not as big as Foxxy’s plus there was a little sag, but he replied that my big puffy nipples were the best he had ever seen and he often thought back on how he got them to stand tall and proud with just his mouth.
I coaxed him to giving the nipples a touch of his teeth, these days that always did the job for me. Once they were standing up he could not get enough of my erect nipples.
I admitted I was interested in getting his beautiful cock to stand up hard in my mouth. I wasn’t big on oral in college, in those days I only took his tip. With my guy oral pretty much dropped off the menu after the first few years, we both liked fucking more. But Roger’s cock looked delicious to me, I often dreamed about having it cum inside my mouth as his cum dribbled out from my lips and ran down my chin. So while he had his way with my nipples I handled his manhood. Then he let me go down on him. My lips had some quality time with his whole business.
I am no oral expert, my husband almost never finishing that way, but this time I was doing it please myself and satisfy my curiosity. Roger didn’t complain as I alternated between sucking his large cockhead and licking his balls.
He noticed this little kneeling pad in the cabinet under the sink, it was a lot easier on my knees. I guess that at a hotel like this, with willing men and well-paid professional women, kneeling in the shower was routine. That image, that this was a temple of commerce where oral sex was done routinely by professional call girls to absolute strangers, made me hot. Also, Roger’s cock and balls looked yummy. So I got into licking and sucking like never before. I was putting on a show for him by sucking on the cockhead, ducking my head down to tongue his balls, and using my lips on the shaft like a cob of corn with my lips. Roger was moaning with pleasure thru it all. He periodically pulled me back up for more passionate kisses.
I said I was not an expert at oral and rarely did such things, but as long as I was getting paid I was determined to be enough of a mouth-slut to earn his cum if he wished it. He said the show was fantastic as I sank to me knees again. I was determined to get him into my throat this time.
When he was fucking me earlier I thought Roger might have a bit more length than Tracy, but when I first tried to take him deep I could not get as far as I usually did. The issue was the very prominent ridge of his cockhead. It was much more than I was used to dealing with so I could not take him very deep.
Using a slow pace and careful breath control eventually paid off when I finally pressed my lips to his shaved pubic flesh, I took him all the way in by overcoming my gag reflex. But I could not hold him there or use it to pleasure him.
My husband’s cock was also thick and long, I honestly could not say who had more meat. But Tracy did not have a wide ridge. So I could take my man moving deep in my throat, which he enjoyed on occasion. In college I sometimes I got a “touchdown climax” from him there.
After I released Roger’s shaft he lifted me up and pulled me close, locked us together in a breathtaking kiss and embrace. His tongue deep inside, after his cock, really packed in his desire. It was sincere and passionate, a real connection. When we broke the kiss he told me how happy he was to be with me “instead of the usual pro with her painted-on smile and her step-by-step gameplan.”
Roger visited our town about four times a years, and since his company did enough business my husband’s firm kept him supplied with a top-notch pro escorts each visit. I knew all the pros could take him deep in the throat so I wondered if he was missing that service I could not provide.
Roger knew what I was thinking. “I have no complaint about what the escorts do, they are pros at making the client happy. But there is also no doubt that it is a job for them, a routine of checking off the boxes as they try to keep a smile fixed on their faces. You have to tell Tracy I am really thankful for this. I can’t hope for it as a regular thing ... but it sure is nice to see you this way.” He was deliberately making a comical ‘big eye’ at my nipples when he said that. We both laughed.
“I will be sure and tell him. But you have to know that you can’t say a word about me at the office. Somebody is seriously screwing with him and his job, when I heard he didn’t have a girl for tonight I would never have volunteered until he said you were the client. He knows I have always lusted after you, so we agreed to let him talk me into this. He knew I have always had sexy dreams about you so there was always an extra sexual draw. Sometimes the dreams involve both of you doing ... amazing things ... to me. I tell him I love him, but sometimes I lust for you. We don’t do this sort of thing with anyone else, we do not have that type of lusting feeling about anybody else. You spoiled me. I promised that I will tell my husband all about it.” I grinned and got a little embarrassed. “I am sure he will have me do a little show-and-tell ... Fuck, that idea makes me hot!”
Roger pulled me in for another passionate kiss, then turned me around, so my back was against his chest. He held me tight but lovingly, with his erection against my bottom and his hands cradling my wet tits. He felt very masculine and sexy, like in college. I felt so good knowing he really desired me.
As he was kissing me on the side of my face, on my cheek and ear, he asked,
“You will tell him all of it? How much detail will you share?”
“Oh, everything I can recall ... I said show-and-tell. That is part of marriage.”
“Most guys would take offense. Doesn’t he have a line...”
“No. He sent me to you for the night and ... well, our fantasies have included much more. Things like watching, sharing serial sex ... like two-on-one. He knows I always wanted to have you, I lusted for you in college. He loves me and sent me to you willingly, because I really wanted it. One of the things we talked about was ‘a line.’ I told him there were some things I would never do with him, because of our love. But that I just might do them with you, to try, because with you it is lust, not love. He was fine with it.”
Roger said, “I never thought of that, but now that you say it I can see the sense of it. Is there anything you want to ask me about?”
As soon as he said that I knew HE wanted something naughty, and maybe he didn’t want me to share that something with my husband. I wondered what?
I replied, “If I do I’ll let you know. I called him when we got to the room, after I undressed. Do you know what he said?”
“It must have been a fast call, I didn’t notice.”
“Well, maybe my legs were holding your ears at the time.”
“Ah yes, I remember not hearing that. What did he say?”
“I told him that I was wearing just my stockings and my rings while I was in your bed, which made me a very naughty married woman. We both knew what you were going to do next, after you finished what you were doing so wonderfully. We would add ‘unfaithful and dripping’ to the list of my sins. He said, ‘What type of husband would I be if I sent you to a lousy lover? You know I want the best for you.’ He meant it, and it is so true.” I was baiting Roger a little, he had a secret desire about me, I could sense it. I wanted him to have me in every way he wanted. But there was something he was afraid to mention.
“Wow ... I really appreciate that. You can be sure that showing you a good time is my first priority.” He hesitated, he was considering what he would say next. Finally he took the risk. “Talking about experiments ... We talked about how Foxxy was so sexy, but did you know that in one way you had her beat?”
From the way he was talking, being cagy, I could tell he was thinking of something way off the union-approved-menu, something ‘he had never done before’ daring. Based on the earlier questions about detail, it was something that he didn’t feel good about my guy knowing. But he wanted it a lot. What could it be?
Then he started to handle my bottom with his hands. Bingo!
Roger whispered, “You always had the cutest buns, with the sweetest rosebud.”
That was way off the menu, if a guy even mentioned anything in that area to a union girl he got sanctioned by the union. For Tracy and me, anal sex was a couple of times a year, when we are both in the mood. (Yes, I got in the mood, sometimes I wanted it.) Sometimes the mood hit us together and I enjoyed giving it up, sharing his need feeling him fuck me there and enjoying him getting off hard there. For Roger the size thing had me a little concerned, because his ridge was wider. Could my flesh stretch that far? I was sure it would hurt.
I stalled for time. “We have already enjoyed good things that are off the menu, hot kissing and pussy licking ... What other naughty indignity for my poor helpless body might interest you?”
“How about I tell a story.”
“Okay...”
“That Fall before you came to campus, Tracy had a nude picture of you, and I kind of fell in love with your lovely bottom. I mean, your face and your breasts were wonderful, but that picture was a perfect ‘bottom’ pose. Then when I met you for real, your bottom was perfect in size and shape, you had Foxxy beat and she knew it. The color and size of your rosy rosebud was a serious desire for me every time I saw you naked.”
“Wasn’t Foxxy enough for you?”
“Really ... she had a bit more than enough ... Honestly, she had great skin, and a super figure, except her bottom was suited to a woman a bit larger. Plus we both knew she would add real weight there in the next five years, it was a family thing. Her rush to California after graduation was to hook a guy before her butt expanded. She was touchy about it so I could not mention anything, especially any desires I had. Even doing her from behind had to be her suggestion, like her ‘forest view’ sex, where I took her from behind while she looked out the window.”
I knew about Foxxy’s sole physical flaw, to be honest when she bent over that part was not attractive. “Well I am flattered that you find my bottom attractive. My guy and I have never done sex things in back, I think every couple tries it a few times, for a time we made anal sex an anniversary/birthday thing. But after the first few years it became a ‘rare mood’ thing. We liked other things more. Also, you might be a little bigger stretching me that way.”
“You misunderstand, I am not interested ... well, not nearly AS interested in that. Anal sex is a better idea than it is a reality. But honestly I do think about ... well, your buns ... I kept the urge.” His finger moved down my ass-crack to brush across puckered flesh. I have to say, from that angle it was interesting. “Maybe, if you are willing ... many times I have dreamed of ... well, the tip of my tongue brushing those forbidden nerves...” As he spoke the tip of his finger moved around, pressing slightly.
He was asking to rim me. That explained why he wanted to ask while holding me from behind, so I couldn’t see his face.
My guy had rimmed my cute back button exactly once, he always said he was tempted because I was so cute. It was different for us that time when we did it, but we never returned to that particular crime. Rimming wasn’t painful, so I really had no basis to object. I had cleaned myself before coming here, I’m just that way - being prepared. I was not mentally ready for anal sex but this... “Nothing deep inside?” I clarified. “I didn’t plan...”
“I can’t say I would not like to ... but the basic desire is just the tip of my tongue exploring around the sensitive flesh ... I never asked anyone before ... the taboo thing kept it off the table. But we have a trust. I would rather nobody knew ... so I was wondering if it could stay our secret...?”
I could allow the act, I could tell he really wanted to. But keeping it ‘secret’ added a complication. If my husband asked for that I would let him, I had over-reacted the only time he rimmed me. Plus I could understand why he might want to keep something so taboo a secret from my guy.
But asking me to swear to keep it a secret from my husband was a bigger deal. Too big. But maybe I could negotiate something in between, a sin of omission is a minor sin. “I guess all lovers need small confidences ... Tell you what ... I will let you do it, but it is with the understanding that I won’t lie to a direct question from my husband. But absent a direct question, I can keep a few moments of gentle rim play as a special secret between us.”
“I appreciate that, I suppose the other really is too much to ask.”
With that he returned to giving these loving little kisses to my ear and cheeks. Meanwhile, with the water running, he used his fingers with more energy around my puckered rosebud. I saw it as a reasonable cleansing ritual before he went down, just making sure. I allowed it, bending forward to open up a little more. I actually felt thrilled by the obscene prospect, plus a little embarrassed and maybe ashamed at the same time, spicing up the feelings like a good sweet and sour sauce.
I felt a shiver of something new. Outside of the one time we tried it during our first year of marriage, I had never imagined that particular feeling ... especially as an intentional request, linked to sex, something explicit asked for. But now, with Roger, it made a daring secret. I grew confident and was looking forward to experiencing the sensation. I was more ‘open’ (in several ways) to it than that first time when we were just playing around.
When he was done preparing me Roger turned off the water and had me change my position and stance, to present myself for him. I felt a thrill as he gently urged me to a pose was obvious and obscene, something that felt both forbidden and tempting. He had me stand close to the wall, leaning forward with my hands stretched up bracing my weight and my legs spread wide. Roger went to his knees behind me, and began giving little loving worship-kisses to my bottom, working around in a pattern closing in on the crinkled flesh at the center.
I would have felt ridiculous posed like this any day except today, with him. What changed? In my mind we were now lovers. Intimates, with secrets of the flesh. He had kissed my lips, my nipples, and my pussy, then put his cock inside my body where we each got off. That joining bound us at some level. I could tell this desire was sincere, my lover really wanted it. I could feel his desire and his care, he had given this a lot of thought over the years.
I cannot say it was a ‘makes me wet’ turnon for me, in fact for me it was not sex but it was more an appreciated gift I was giving him. But I did feel very appreciated by this handsome, experienced man on his knees. I was giving him a forbidden thrill, a way of worshipping my body, doing something taboo he had wanted for years. I was allowing him a prize he thought was unattainable.
The kisses got closer. When his wet, probing tongue made contact with my pucker I felt the conditioned shame run through me, something that came from my childhood programming. Those memories predated my ability to recall so they were a real struggle to overcome. But sometimes desire to please can open the mental block. I forced myself to allow it, forced my body to relax and accept. I made it an experience, I cataloged my sensations as his tongue explored.
I wanted to be more open so I called for a shift. I took a step sideways, I moved us over, so instead of my arms holding me from the wall the sink was against my waist, supporting me, bending me over more. Then with my hands free I could reach back to spread myself open for him. I was presenting myself, I exposed and stretched my puckered flesh as an offer.
Roger groaned in delight as his tongue made greater contact with the the taboo flesh of my muscle. I relaxed. Overcoming more mental hurdles, I made myself push out slightly, making it a willing kiss. He sighed, he was very grateful, his actions said he understood what I was doing and was beyond thankful.
Once I overcame my emotional barrier about the act I must say there was a purely licentious physical pleasure. Sinful and indulgent. It felt fine before, when he was kneeling kissing the cheeks of my ass. But now as he plied the center it became an obscene and decadent delight. His tongue stroked the sensitive flesh around the circle, flesh that was packed with nerves that he triggered, giving me some real stimulation. I moaned at the unique pleasure, his tongue stroked my ego as it tickled my bottom, it felt so damn good. I found myself leaning into it, stretching myself more, pushing out more, giving myself to the obscene feelings. I imagined what I looked like, totally lewd and decadent.
What sort of woman could willingly know such pleasure? Only one who was loved, or indulging obscene wealth.
I realized that the act brought a dual feeling, I felt both raised up to a focus of worship as a most desirable woman while simultaneously I felt like the dirtiest of whores. Wow!
I glanced to the side where I saw the full-length mirror showing us partially in profile. I looked totally hot so I called it to Roger’s attention. “Can you believe, I have never seen myself having sex. Such a thing to see, it looks sinfully ... and hot.”
He turned his eyes and saw me watching him. It was like those soft-swing moments long ago, when we each watched our lovers across the room in the exchange, they were kissing passionately and giving their bodies to another, fingers sharing pleasure and arousing all, the watchers and the watched. Except this was much, much stronger. Because of the position and what he was doing with my ass I felt more than naked, more than intimate. I was so nasty to accept his purely lustful kiss.
Watching our reflections my mind filled with other ideas. Desires. New imaginations sprang to mind. “When you are ready I want you to stand up and put it in me from behind. I want to see myself as you do me like a whore, taking your pleasure from my body without seeing my face. That seems to me to be a more sinful, more provocative act. Use your hands on me as you do it, like I’m paid for to be used by you for the night.”
His cock, where I saw it hanging between his legs, moved as I said those words. I added more. “Go ahead, forget the college play, tonight I am your whore. I will be gone in the morning. Show me how you treat a willing, lustful whore without the damn rule book peering over your shoulders.”
I felt his control slip, he was inspired to up the obscene kiss, pushing harder, probing the entrance. But once he had his obscene taste of me he gave way to other carnal desires to take pleasure from my body. He was hard and didn’t need more convincing. So he stood and we both shifted our position a bit. The mirror gave us both a better view. It was truly different seeing this man do me. I froze as he slowly positioned his cockhead and pushed into my pussy from behind. My abundant fluids made me easy for us. I wanted it, my body was bent to accommodate a man, the pose was similar to that nude picture of me Tracy had displayed so long ago. The S-shape curve of my body profile in this pose made me look more sensuous. For somebody of my age I thought I looked pretty good posed to get fucked.
When Roger turned to look at us in the mirror I felt his cock jump inside of me, testifying how I looked to him. He said I looked a lot better than pretty good, a lot better than a hairy old man like him deserved. This profile view was the hottest he had ever seen. The directness and posing made this act one of pure fucking lust.
Once he had his full movement he reached around to pinch and roll my nipples in his fingers. It was strange to both see and feel this indulgence at the same time. To me my tits normally sagged, they were big enough to show the sag but not big enough for anybody to call them big. But from this angle, they looked pretty good hanging from my chest, shaking as he fucked me. There was a richness (like a flavor) to it. He pinched and played with the nipples like it was his right. I had known such play before, but I had never seen my body played with in such a crude, selfish way.
He pinched and pulled as we both watched, his fingers seemed to be abusing my tender but willing flesh. He was a new face doing what he wanted without the familiarity of that line between what feels good and what is too much. I was okay with that. I stressed that my feelings didn’t count. He took me at my word so he was harder and more energetic than before, at the very edge of ‘a little out of control’. The feelings were made stronger by my watching him take pleasure, treating my body as a sex toy for his masturbation pleasure.
There was some discomfort in what he did to me, he crossed that fine line between pleasure and pain. I actually felt freed by the fact that he didn’t know or care where my line was, he was doing what pleased him as his cock moved in-and-out of my body. I felt more like a whore.
I found myself asking for more. “You can be rougher, take more if you want. I know more is what you want.” As I spoke I heard in my voice how I was right at the edge of pain.
He did want more, he slipped loose of the last bit he was holding back. He thrust harder. His hands took tighter unyielding possession of my body, one hand held my body as a possession, so he could use it. His other hand stretched, twisted and squeezed my breasts, one after the other, his fingers digging into the flesh of my breasts deep enough so it looked like they would leave an impression. He whole body language and face changed as a darker spirit of lust took over, he went from lusting WITH me to a complete indifference for my body. He was using his cock to take his own more extreme selfish pleasure.
Fuck me, I wanted to be totally used by Roger. I was the object of his lust, and he of mine. It was a level of lust the man who loved me could never force himself to do.
Our eyes met in the mirror where we both acknowledged the change to darkness, he was not “loving” me, he was not even my old friend just now. Instead he was giving rein to a darker part of himself with a whore’s body, using me for things he could never ask for. He was crudely jerking off, my body had become a disposable tissue with extras fun parts available.
I felt rudely used, and I was enjoying it even more because we both felt exhilarated by the freedom of use he was taking. In a way I felt more purely female. How many women in the world, right now, were being used by a man this harshly and loving the feeling?
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