Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 4: Somebody’s Watching Me
Erotica Sex Story: Chapter 4: Somebody’s Watching Me - I thought my old college friend Roger would be my first and last time as a whore, but Cupid made other plans. The Joker took advantage by messing with my guy’s biggest client. I had to get this done or jobs would be lost. This time it was the real thing, I had to whore for a stranger who was known to pay more for a girl going outside the rules. A lot more. He was a nice older man who wanted my ass, and as an extra surprise he brought some family! (All over 18.)
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Teenagers Heterosexual Fiction Sharing Slut Wife Wife Watching Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Sex Toys Prostitution
(In this case the “Kids” are adult children, 18 to 30. No minors are involved.)
This hotel suite had a “old west” motif, which included a few of the ornate 3 panel “Chinese” screens like one sometimes sees. In Westerns that show a hotel room such screens might be used to screen a bathtub. In more modern movies such a screen might be used for changing clothes while others are in the room. In this case the five-foot tall screen was in front of a door on one side of the suite, I could see the top of the door which was behind the screen, but I did not notice when the door opened or closed. Besides the main door and this screened second door there was a third door on the other side of the suite (I learned that led to Mr. G’s bedroom) plus the door to the bathroom, which was open.
Mr. G was naked on the bed, sweaty, and dripping, when I glanced at the sound where I saw three sets of eyes peeking around the screen looking at me.
Mr. G noticed what had my attention and spoke. “Well, I see your other clients have arrived. Come on out children, don’t be shy ... in a few minutes I imagine you will be beyond that with this wonderful woman.”
Children?! He used the word “children” for them. Also “clients,” in the same sentance. I considered myself a decade beyond doing things with children. I was naked, covered with sweat and dripping with their father’s(?) cum.
He signaled me to stay as I was, on the bed, naked on top of the covers, sweating, and I imagine looking well-fucked. Normally I would not have obeyed, but something told me that nothing would be gained by moving, except showing my body to these children from different angles.
As the trio came in and gathered around the bed Mr. G addressed me. “During our negotiations you noticed that something was glossed over. Now is the time to explain, but first I should introduce you to my children. I will start by saying that all three are of age, that is they are older than 18. All are, in fact, my legal children and heirs if not all children of my blood.”
My first thought was that I did not feel good about “children” watching me fuck their father, it was slightly unwholesome. But that had already happened so I didn’t say anything.
The three visitors were all wearing white bathrobes, suggesting that underneath they were naked as me, and that I would soon see them. Putting the picture together I gathered that the suite had three bedrooms, this the central main room with the attached sitting area and table, fireplace and general furniture. The extra bedrooms flanking on either side. I gathered the children had been elsewhere when I arrived, but had entered their bedroom from the outside while my pussy was occupied by their father. They probably undressed and entered this room via the door that was behind the screen. I had no idea how much of the act they saw, but I had a feeling that was not going to be a significant issue by the time they were done with me.
Mr. G made the introductions.
The first young man, who looked about 30 give or take, looking like his father except for the age and the short hair, was Michal. “My friends call me Mick,” he said. “I am pleased to meet you.” I was naked but he put out his hand to shake so we shook. Since he was in a bathrobe I gathered we were going to be very friendly soon. I didn’t pose or vamp, but I didn’t try to hide anything either. His gaze was flattering, he was looking forward to having fun with me. His father continued saying the young man was starting to take over the firm in a gradual handover. Mr. G had mentioned that he was a widower, now he said his wife, who was Mick’s mother, had died of complications at childbirth.
The second person was Gabril, or “Gabe.” Mr. G said he, along with his single mother, were adopted at birth. He looked to be about 28, give or take, and had a strikingly beautiful androgynous face. He looked nothing like Mr. G. Later, when Gabe took off the robe, I noticed his small, but very feminine-looking breasts. The androgyny was nature, not makeup or surgery. Medically he was a rare ‘chimera’ which is sometimes the result of a “lost twin” where twins are formed at conception but after implantation each twin absorbs parts of the other. His body had 2 distinct DNAs in different parts of his body. Sometimes the lost twin is manifested in particular parts of the body. Gabril was mostly male, and performed as such (as I was to discover) but his chest, face and some other organs had female DNA. He was tested extensively from birth. His mother declined to have him “normalized” by surgery (as is often done with visible features). His case was fairly rare.
Gabe’s mother was a long time family maid who was seduced by another employee, a married man who was embezzling. Since the maid was like family Mr. G adopted the infant and the mother, which allowed them to stay together. The maid acted as surrogate mother to the children. At the time Mr. G was still very emotionally attached to his late first wife so Gabe’s mother stayed an employee, not a spouse. Gabe was the most open about looking at me. Based purely on looks I was receptive to his natural charm.
Without surgery Gabril would have had serious problems in a normal high school, but the two brothers were raised together and home-schooled until college. Mick added, enthusiastically saying, “My brother and I are really into teamwork together.”
Gabe agreed with enthusiasm. From their looks I realized I might be the object of their teamwork.
The third child responded to her brother. “Take it down a level boys, can’t you see she is having a hard time with Dad’s surprise? Maybe she isn’t that experienced. I don’t blame her.” This was from a mature sounding teenage girl with a slim figure and red hair.
“This is my dear Ariel,” Mr. G said. After a decade as a widower, Mr. G married Ariel’s mother who brought her 10 year old daughter into the marriage. Her mother had given her no sense of stability before that. Two years later this second wife and Mr. G had a amicable divorce, they had grown to far apart for a day-to-day marriage in Kansas, but the second wife still visited every year. During the marriage Mr. G adopted the girl and when the couple parted they concluded that Mr. G should raise the girl, as the mother could not see her life styling with a teenage daughter.
I could do the math. Gabe’s mother had ruled the roost for two decades raising the two boys. Suddenly another woman was there with a female tween. Tweens can drive anyone crazy, and with two women in the house it was probably a catfight every night. Then the interloper leaves, and the surrogate mother, who thought her time as an active parent was over, was suddenly had responsibility for Ariel’s teenage years.
It would seem like punishment for doing a good job with the two boys, and could hardly be a solid basis for a parent.
Mr. G explained that this trip was a birthday present some months after Ariel’s 18th birthday. “She was very determined to see people having sex and we really could not think of a better chance to observe. Her brothers convinced me that I have sheltered her from too much in life, ‘keeping her like a princess locked in a tower.’ She is the ‘observer’ I mentioned in our negotiations. Ariel has agreed to watch, but not touch.”
Ariel immediately added, “I hope that is okay with you. The guys said that it should not a problem, they traveled with Father before. I could have peeped surreptitiously, but I would not feel good about that, so I insisted that Father include it in the negotiations.”
I had agreed to an “observer” so I really did not have anything to say except “welcome to the show.” I gathered that her brothers were okay with Ariel watching them stick their wet boners into my body. Then I thought back to that ‘teamwork’ comment and considered that maybe Ariel was in negotiations about ‘joining the team.’
After the introductions were done I had to ask Mr. G, “You used the word ‘clients’ earlier, which implied something more than ‘show and tell’ with you. I am not clear as to when I agreed to ... well, anyone but you.”
Mr. G expected to explain it. “Actually you did, and you knew it, but by design you lacked some specifics. Let me share some history. Five years when Mr. Maier introduced me to the delightful Ms Vee, I was traveling alone but I had a desire that was resisted by most escorts. Mai and I agreed that our meetings would be both on and off the books so they might include some uncommon services. I have negotiated with her each year since. Three years ago was the first time I brought Michal along, and while he did not meet Mr. Maier for our business meetings, he joined Mai and myself in the overnight activities. He was a late addition, she agreed for a surcharge on the usual fee. We took turns, we each sent her to the other when we were done, back and forth. Mia appreciated not having to do a tiresome cleanup between us. Afterward she said the she enjoyed serving the two of us in turn during the night, but suggested that in the future she might stay in one bed and we could take turns coming to her. That really was a better idea. Two years ago I brought Michal along for both business and pleasure, Mr. Maier met him briefly but was not privy to the nighttime arrangements. Last year I brought both boys along, they were checking out the production lines while I was meeting Mr. Maier, so his notes might have omitted all mention of the boys. Last year Mia negotiated to serve myself and both boys, and became acquainted with their preference for teamwork in the form of a DP. I would say that they all enjoyed it. The price we agreed to tonight is in excess of the percentage that Ms. Vee had negotiated last year, because of the added observer.”
I got the point. “So when we negotiated, I agreed to ‘accommodate what Mai did last year’ which included your sons. I assume that the reference to ‘teamwork’ implies your sons enjoying front and back at the same time. I knew it was too good to be true.”
“Yes, I recall your statement to that effect. I implied at the time that I was taking advantage, but given my age I believed the surprise would not be too much for you...”
I had to cut in on that with a comment. “Based on what you did to me so far you don’t have to apologize for your age. It was quite delightful.”
“Why, thank you for that ... You will see what I mean, I am told the boys are uniquely well suited to the activity. Now, as a clarification, the boys prefer the DP to other forms of teamwork.”
“I wonder, considering your own abilities ... is ‘watertight’ in my near future?”
“No. I have a busy day tomorrow so I need my sleep, plus our delightful exercise will surely exhausted my ... hmm ... my ready supply of enthusiasm ... for now. You will have this room for the night, the others have beds in their room and will come and go as they are moved. For myself, I set an alarm to get up at 6 in the morning, and my preference for a wake-up exercise is anal sex in the prone position. I will wake you up. Given how attractive you are, I may be quite anxious by then. After the boys it should be no trial. Again, do not concern yourself with cleaning up, my sons and I have shared women sequentially before. You and I will share a shower in the morning after we finish. For now I bid you good night, with the suggestion that you might ask your clients to join you in the shower before starting, so you can all get acquainted. Are we clear on things?”
It seemed we were. Then Mr. G made a final comment to the boys. “Boys, pleasure with this one is special ... she is new to the profession and very sincere, her pleasure is not an act, so if you are successful you will be rewarded. She is a prize ... if you are up to it.”
He turned to me. “The boys have a bit more enthusiasm than I do, so the ‘working together’ will come later. You can get to know them individually first, followed by the DP. Either or both my be inspired for a third shot before I got up. I expect you to have an enjoyable evening. Until 6 then.” With that he left for his bedroom on the opposite side of the room.
Suddenly I was alone with two more young men to satisfy while a young woman watched. The biggest question in my mind was that, if I was going to fuck these two, I really needed to get some idea about the size of their equipment. Mr. G knew my concern, no doubt that was the reason for his shower suggestion.
I looked around and decided that I might as well get the party started. But before I could move Ariel had a question. “Excuse me, but I noticed your rings. Are you married?” I recalled that her mother left at least two husbands, and possibly other men as well as her daughter. So I recounted my rehearsed answer of widowhood plus a new friend.
“I was married once, it ended with a fatal accident. These rings remind me. I am currently in a relationship, but we are not sure yet ... let us say that we share a roof together on some weekends. He knows what I do, and one issue is that he is not sure about this job extending after marriage. But for a time I was an attendant on a private jet and that was worse, sort of more sex with less pay.” They all grinned and nodded that they understood. “Also, I should mention that I am very new at this, it is my second date.”
I continued. “But since you asked I have to wonder, do you wish to do anything more than observe? I am not volunteering, but I imagine that passively watching will not be much fun.”
She gave a naughty smile. “It will be more like watching with toys, as I have my own along. I have known another’s hand, I made a few silly mistakes in high school, and also enjoyed pleasant moments ... with boys and girls. This is my first time watching my brothers, the whole trip is a present for early graduation from high school. Father and I have talked about a ‘coming out’ party for me sometime, it might be with several people. I guess I am not sure for now.”
I was not going to take that farther. “Well then, shall we?” I motioned to the bathroom. “Unless you prefer...” I motioned to my messy crotch.
Ariel was quick to prod the boys. “Get those robes off, you know damn well she wants to see what she has to work with ... you are never shy on my account.”
The boys slipped out of their robes, but they were soft so I really could not tell too much about what I was facing. I took their hands and led them to the shower.
Ariel lagged behind, but I asked if she wanted to observe so she dropped her robe and followed us, taking a seat on a bench while I adjusted the temperature of the shower. I noticed her pubic hair, like her head it was red. I gather she had never cut her pubes.
I was shaved completely bare down there.
The young men seemed very easy to deal with, I guess they learned from their father. It was like they acted as if I was in charge of them, even though Michal seemed be older than me and Gabril might be close to my age. They were cautious putting their hands on me, gentle and the opposite of grabby. I was sweaty from sex, and their father’s sperm was seeping my pussy, so they offered to wash my body. We all knew what was intended in terms of their fingers and my privates. I smiled and said “please.” As they ran their hands over my front and back I had to ask what they planned to do with my body once the playtime started.
Michal responded. “Individually we like the usual, maybe different positions. The truth is that we will be quicker than dad for our first shot. We really like a DP to finish, it is the ultimate teamwork to share my climax inside a woman with my brother. If we are all getting off together it can be double or triple the fun.”
Gabe volunteered, “Once we start the DP we don’t switch holes ... we figured you would want an assurance about that. He is front, I am in back.”
Michal’s stiffening cock might be a little thicker than his father. He said that they found sharing a woman between him and Gabe was a bonding experience, but it was something they built up to, it was not a place to start. “We want to become intimate in stages, steps that seem reasonable as we alternate pleasing you. We have been taking turns and doing DPs since Gabe was 18. We hope you can feel relaxed about it.”
Gabe’s cock was much thinner than his father, think a hot dog or maybe a long hot dog. He went to the obvious issue. “My breasts as not as sensitive or responsive as a woman’s. Yours are spectacular by the way. I understand a natural tendency to touch or suckle ... I enjoy such acts with women when they are gentle, but the sexual connection - female breasts and male genitals - is weak at best. Also, the thing about DP is that the benefit comes in working together ... feeling the other moving against me inside. It is best when the woman responds to both. We are not gay in any way. But like he said, feeling a woman together is a bonding experience we enjoy sharing.”
“Have you ever reversed those front and back preferences?” I asked.
“We both like vaginal sex,” Mick said, “so that will be the first round. We tried reversing the DP once, but the feeling for us just were not the same, and for the woman that is usually a firm ‘no’ on that.” I grinned, as I felt him his girth seemed a bit bigger than his father, and but the greater concern was a more prominent ridge. “There was one woman who talked about double vaginal, but we were not interested in that either, it struck us as maybe a little too gay. I mean, we were raised as brothers all our lives, so we didn’t need that.”
“Plus the leg arrangement ... impossible to please,” Gabe said.
From what they said I was pretty sure I could handle them. Also, they were so nice that I did not feel that ‘too much’ was being asked of me. It would be more work than I expected, but that really depended on how you defined ‘work’ for me. I reminded myself that I had enjoyed their father completely, twice! It was a great workout with extra smiles surprising me. With that I invited them to press against me and use their hands to cleanse me internally with a finger or two, as a prelude for later. I was curious. They were not shy and did not waste time, but they had trimmed nails and were careful enough with my delicate flesh so I had no concerns. Gabe waited until he had my okay before his finger carefully entering my pucker.
Ariel watched closely as the fingers entered me, watching this was something new to her.
Given that I expected anal sex tonight I had prepared myself internally. Gabe pressed his body against my back and side - it was a unique feeling, nothing like Foxxy because of the size and muscles - as he gently worked his finger into my tightness. His entry move suggested medical training, there was a quick rotation.
Once Gabe’s finger was in Mick stepped closer, his body was pretty solid muscle and felt very masculine. One hand cradled my head, that felt romantic, as he kissed me around my cheeks and forehead. It was a nice touch, more friendly than overly familiar. After getting my attention his fingers started to part my labials. His father’s cum was all over down there, I was still dripping, but he seemed to give the mess no consideration. I admit some surprise, but this was not their first trip with father.
It took some time for them to start working together, moving fingers in and out of both holes, but when they started I got it, my body was their shared connection. Getting into the feeling I invited Mick to try a second finger. When they got that organized they began to finger me like they were practiced at it and suddenly I was overcome standing between then. It was not a full climax, but I knew it was a type of release. I half expected a passionate kiss. I had to hug Mick tighter, and close my eyes to focus on the feelings. When a spare finger started to play around my clit I admit that I shivered and got a little emotional between these two young men I had just met who were showing a new path in the garden of pleasures. That did not go on too long, and when the moment ended they slowly disengaged. But we all knew it happened, and would happen again.
Both cocks were very hard for me, I had to handle them gently. The sizes were quite a contrast, with Gabe so slim and Mick was more meaty.
“It seemed to us that you liked that,” Mick said softly. I recognized that for what it was, an considerate way to let me down and disengage easily. It was mature and appreciated.
“Yes, it was very nice, appreciated. Let me thank you two for the good feelings.”
I looked at Ariel, I could not tell how deep she had felt things. She was focused at where her brothers had one of their fingers in me - her look told me she had never felt male fingers deep inside both holes like this. Well, it was new to me as well.
It was a little distracting for me to be the center of attention, so I tried to distract. “Whoever gets these two will be very fortunate, I am sure of it. Maybe a pair of sisters ... or maybe one is enough for two.” She smiled at the first suggestion, but she blushed at the second! Why would my comment get that reaction?
I thought quickly about their biographies, there was no common blood, and they all knew it. The three were obviously comfortable with each other. Maybe things had been discussed ... or more.
Come to think of it, their hotel bedroom probably had only two beds, so they might share in some way.
Wondering if the guys noticed I changed tracks by asking Ariel, “Your Father and I, how close to the end were we when you came in?”
She said that it was not the first time she had seen her father with a “woman in bed.” It happened at home. Tonight they came in when I was peaking with my solo climax. She said that she could tell I was really enjoying it, not faking. She was also a little in awe at the intensity of the climax I shared with her father. “I did not realize that Dad had that in him. But your response was something I can shoot for someday.” She hesitated for a minute, then added a comment that circled back to her blushing. “My brothers know the facts, I have not had full sex with another person yet ... I have enjoyed toys but not the real thing. If ... well, with no blood between us ... we are so close ... so we have talked about sharing becoming a three-way thing with us. Rich people often find arranged marriage a useful solution for keeping wealth in the family, for the good of all.”
I moved my lips to ask without a sound, “Lucrezia Borgia?” I doubted that all the stories of her brothers and her lovers and her husbands were true ... but there were a lot of stories.
Her reply, was to blush and smile. “I have read many interesting stories.” Ariel was clearly an educated woman.
In that moment I got a sense of Ariel’s life. I bet she had no friends. Abandoned by her mother, with a busy father, she had Gabe’s resentful mother as a surrogate parent to say “no” to girlish requests. She lived on a large estate and was socially isolated there. They probably lived in a one-company town. If Gabe required private tutors and she probably did also, the economic gap would be difficult. But now she had finished her tutored high school work and I imagined she would enter college next fall - if she was so inclined. The choice of a new, foreign and unknown society must terrify or fascinate her. Maybe both. Ariel really needed a friend, a young female she could talk to.
I always said that finding the right person was a big deal for me, I had seen too many relationships go bad because they were in a hurry. So I shared. “I met my husband as a freshman in high school and outside of a brief separation due to schooling we were never apart. We got hooked soon after college.” That surprised her because we held out so long, but I said we were friends first, that was important. Also, “I did not mean we waited until marriage for the fun part. We were fortunate that our desire grew in both of us at the same time - the exact day I started college.”
At this point I had both cocks in my hands, getting them firmed up and keeping them interested while I talked to their sister.
I reminded her, “As a widow, I have had lovers, but I have been picky and dodged some bullets by stepping back when things seemed to be rushed. I am new to this profession, I know I am starting late and to be honest it is easy to have a good time with your father. Plus, now I get these two to ride. YUM!”
I addressed the boys. “If you are done, maybe we can all move to the bedroom so I can get started trying your cocks on in some different ways.” I guess that was what they wanted to hear because the water was turned off and they were eager with a flurry of towels. Despite the “don’t touch” rule Ariel helped in drying all three of us. When that was done we made our way to the bedroom. I invited the two boys to sit on the bed next to each other where I could size up their cocks with my mouth.
When I got down between them both cocks had softened so I alternated licks between them. They stiffened up quickly, I started to take them into my mouth as they grew.
I discovered Gabe might be a little longer than Mick. Part of it was because of the build of the two bodies and where the cocks were mounted. Mick had a stubby body, like his father so his belly protruded farther from his spine more than Gabe, who was whip-thin in his waist and hips. So it was like the base of Mick’s cock was somewhat buried in his body, where Gabe started “out there.”
However, I did not share my observations.
Once they were erect I started to fellate them for about fifteen second each. I kept my hands behind my back as I did it, I wanted Ariel to see it all. It was no surprise that the guys liked my actions.
Ariel said that she was surprised that the guys did not pop with just a little contact. I explained that I was not deep-throating either of them, I was not up to that. But I said the stimulation was more from watching it happen, plus the head trip based on social ideas of behavior formed as children. “Honestly, the physical stimulation is not what a guy needs to trigger, unless a guy has a hair trigger, either naturally, due to his age, or from his state of anticipation. Experience has a lot to do with it because of the emotional part. These guys are experienced, aren’t you? I’m guessing with professionals?”
Both guys said “yes” to that, I bet their father gave them little time to date.
When their cocks were fully hard I got on the bed and invited them to have at my breasts. “I know you want to.”
From their reaction I was right. They each took a side and began sucking, kissing and nibbling. “Fuck me, these puffy wonders are fantastic,” Gabe said.
“You got that right ... if yours were like this I would be all over them,” Mick said to Gabe. “I know that sounds queer, but some enjoyments are beyond that sort of thing.”
Suddenly Ariel shot out of her chair, ran across the room to her father’s door, and went in. “Do you think he will okay it?” Mick asked Gabe.
“She can be very convincing, and you have to admit, these beauties are special,” Gabe replied. “Once in a lifetime treasures.”
“What are you two talking about?” I asked.
“No talking please. Let’s just wait and see,” Gabe replied.
With Ariel gone they both mentioned how attractive my pussy was, like the nipple it was unique. Mick finally asked the question, “I know it is not usually on the menu, but would you mind if we had a taste? I’m sure...”
I cut him off. “Well, I wasn’t here last time, so I am sort of at your mercy about what I negotiated to allow ... What did Ms. Vee allow? You have me in a good mood ... I guess there is no harm in trying. Just keep it clean.”
They did a quick silent rock-paper-scissors thing where Gabe got the first crack at munching my snatch and getting a taste of my pussy juices. I am sure he had no idea he was my third guy ever using his tongue down there, his Dad had passed on eating at the “Y.” But Gabe was appreciated. I put a pillow under my ass and spread my legs so he had good access. He used it.
Gabe started at the top of the slit, because my inner lips are essentially non-exitant he seemed fascinated by how the lips split off. Then, as he worked his way down, he ran into moisture. “She has a valley of wine and honey, a regular spring of sweet juices,” Gabe remarked.
I cautioned him that his father’s fluids would drain for some time, but he said it was no problem. “Dad taught us about cream pies, we don’t mind the occasional taste of home cooking.”
Mick was still engrossed in my nipples, he took over both “so one would not get cold.” He acknowledged his brother with a surprisingly articulate grunt, it sound like, “I can’t wait,” but maybe that was my imagination.
Both boys were doing a job at working me up, it felt very good. I had never had two lovers before, I often dreamed or had fantasies of my husband and Roger, but there had never been any moves in that direction in college. On the other hand, we were only together for the one semester before Roger and Foxxy graduated. Now Roger did not have any regular pussy, he just got one-shots when traveling for business. He implied he would travel for a long weekend of shared enjoyment.
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