Man must audition sexually for fiancee’s family.
Part 1 of 2, by deadeye_76, listen to the Podcast at Steamy Stories.
Wednesday night before Thanksgiving, 2010:
“Your family wants me to do what?!?!” I said this in a harsh whisper to my fiancé. We were in her bedroom at her family home on the Wednesday before Thanksgiving, having gone there for the weekend. What she had just told me was shocking. I couldn’t believe my ears and she was sitting there looking shocked and stunned herself, tears forming in her eyes. I started pacing and thinking about what I should say. But first, let me tell you how we got to this point.
Fall, 2009 I met my fiancé the year after we both graduated from college. We were working at the same company, both at the entry level, her in the Human Resources department and me as a database administrator.
One Friday as the Thanksgiving and Christmas holidays approached, some of the folks from the company went to a happy hour. There were many people there and I noticed Gwen right away. She was a little reticent to get caught up in the unbridled joy (or stupidity depending on your point of view) that some people were exhibiting. She was smiling and laughing, but seemed a little reserved. She was blonde, very pale, and had a tiny bone structure. She looked to be no taller than about 5'2", but I couldn’t tell for sure. I went over to the table where she was sitting and said hello to one of the guys that was there that I already knew. I was hoping for, and received, an introduction to her. I noticed that her eyes were a little green, but seemed to run toward hazel. They also captivated me and I caught myself staring at her a few times.
Soon it was approaching 8pm and we had been there since about 5:30, so I decided to go to the restaurant next door and get some dinner. I told my friend this and then looked at Gwen. I was never very aggressive with my approach to women and was a little shy about asking, but somehow I managed to ask her if she wanted to join me. She looked down at her drink and then over at her friends who were, in my mind, making fools of themselves in front of some of the company managers. She looked at me and smiled. She agreed and I was inwardly thankful that I had gotten up the nerve.
When she stood, I got a better look at her. She was maybe 5'4" and 110 lbs. She looked to be athletic and in good condition. She moved like an athlete and since I played baseball in college, I figured she might have played some sport, too. She was wearing nice jeans that accentuated her slender stature and tight butt.
Over the next couple weeks we dated a little casually, nothing too formal. We were taking it slow, mostly because she wanted to. I wanted to take it slow for a while, but being around her was driving me nuts. She seemed to ooze some pheromone that was making me hornier than usual. She was also living alone in a nice apartment while I was living with a roommate. She must have come from money, but she never told me anything about her family or situation.
For Christmas, Gwen was going to be heading home to be with her family. She had finally told me some things about them. I had learned that her father had died last summer and her mother lived alone in a big house. Her two sisters were older than her and married. The oldest had two children and the younger one just one child. They were all going to be there for Christmas and I could tell she was looking forward to being with family. Just before she left, I took her to a very fancy, very upscale place. I told her to dress up and she didn’t disappoint.
Things progressed quickly from there. I found that while she was a little demure in public, she was, underneath it, a fiery, opinionated, outspoken woman – and I was slowly falling in love with her. She told me one night in May that she was in love with me and watched me closely. I could feel her gaze as she carefully watched how I responded. I just smiled, stared back into those eyes, and told her I loved her, too. Apparently, I passed her test because she ripped my clothes off and had her way with me – several times that night. It took a week to wipe the grin off my face.
By July, we had become a couple that people described with both our names. It was only a matter of time, in my mind, before we got engaged. I decided that the best time would be after she returned from her summer vacation with her family and me with mine, which made it Labor Day weekend. We were both going to see our families the last week of August, separately, and would be back for that weekend. I had a key to her place so I set it up in a manner that she would appreciate. We were both hopeless romantics and I knew she would really appreciate the effort.
I shook my head. She and her mother were close. Her father had died the previous year and they had become even closer. I loved her for that, too.
She finally put her phone down and went over and plunked down on the bed. “Okay, let’s eat something here.” She eyed me. “Somebody is going to need their strength.”
I grinned and reached into the pocket of my robe for the last part of her surprise. She was just finishing her first cracker and had reached for her champagne. I put my left hand on her arm and stopped her. She looked up at me questioningly. I smiled and slid off the bed onto my knees. She was still looking puzzled until I held up the small ring box.
I was unprepared for her reaction. She screeched and threw herself at me. She tackled me better than anyone had when I played football and ended up on top of me. I was being assaulted by lips for the next 2 minutes. She kissed me on the mouth, all over my face, and then my neck, before returning to my mouth. Finally she sat up and grabbed the box that I was still holding.
I grinned at her. “Is that a yes?”
She ripped the ring out of the box and put it on her finger before she answered me. She looked down at me and smiled. “That was a hell, yes, don’t you ever think about taking it back.”
By November, we had made arrangements to spend Thanksgiving with her family. And that’s where we ended up today. We are sitting in her bedroom trying to wrap our arms around what her mother had just told her. It was unthinkable to me. Her mother had told her that her two older sisters both had sexual duds for husbands. The husbands were not adventuresome, were not good at taking care of their wives’ needs, and were not interested in even learning how to please them. Her mother had told Gwen that therefore, since just she and the three girls were there that Thanksgiving, having left the families to visit the other relatives, she and Gwen’s two sisters were going to audition me to be a good husband. They would each spend a night with me to ensure that I knew how to take care of a woman sexually.
I thought and thought about what to say. Her mother and sisters were attractive enough. There was nothing disgusting about it physically, but something didn’t seem right. How was I supposed to answer this? Her mother had become Gwen’s closest friend since her father died, so she was shocked and dismayed. I guess there was only one thing to say.
“Gwen. I don’t like it, but I will do whatever you say. If you want me to do it, I can handle it, but only if you can. If you say no, I’ll back you 100%. I have no idea what you think, but I’m behind you. Tell me what you think and what you think we should do.”
So here we are, Gwen and I. We are sitting in her bedroom trying to wrap our arms around what her mother had just told her. It was unthinkable to me. Her mother had told her that her two older sisters both had sexual duds for husbands. The husbands were not adventuresome, were not good at taking care of their wives’ needs, and were not interested in even learning how to please them. Her mother had told Gwen that therefore, since just she and the three girls were there that Thanksgiving, having left the families to visit the other relatives, she and Gwen’s two sisters were going to audition me to be a good husband. They would each spend a night with me to ensure that I knew how to take care of a woman sexually.
I thought and thought about what to say. Her mother and sisters were attractive enough. There was nothing disgusting about it physically, but something didn’t seem right. And how was I supposed to answer this? Her mother had become Gwen’s closest friend since her father died, so she was shocked and dismayed. I guess there was only one thing to say.
“Gwen. I don’t like it, but I will do whatever you say. If you want me to do it, I can handle it, but only if you can. If you say no, I’ll back you 100%. I have no idea what you think, but I’m behind you. Tell me what you think and what you think we should do.”
Gwen looked up at me. I hated laying it on her, but I had to know what she was thinking. “This is all a lie. There’s more to it than what you have been told. C'mon.” She held out her hand and I took it.
Gwen led me into the dining room where her mother and sisters were sitting, sipping wine and waiting for my answer. They looked almost as tense as Gwen, but I could not figure out why. There was definitely something more going on here.
Gwen led me straight to her mother. “Mom, I want you to tell John the truth about this. Show him the paper.” Her mother hesitated and just looked back and forth between us. “Now!”
I had never seen Gwen this demonstrative with her mother and her mother must not have either. She jumped when Gwen said that. “Okay, honey. But he has to agree to keep this a secret, okay?” She looked at Gwen and then at me.
I was unable to understand what they might be talking about. I looked at her and then Gwen. “Sure. I can keep a secret.”
Mrs. Thurman got up and walked over to a drawer in a small secretarial desk. She opened a drawer and pulled out an envelope. She walked back over to us and stood there looking at Gwen. She finally took a deep breath and handed it to Gwen. “We have to proceed very carefully.” She looked at everyone. “Sit down, John. Okay, Gwen, show him.”
Gwen turned to me and handed me the envelope. “Please, please, read this completely before you say anything.”
“Sure.” I didn’t know what else to say. What the hell was in this envelope? She let go of the envelope as I took it and sat down.
I opened the envelope and read the letter that was inside.
“Ann, I know that I am dying at this time. There is nothing more that can be done about it. However, I have a few things to get off my chest. First, I know that you are a slut and that you have been having affairs for the last few years. I also know that your first two daughters are sluts as well. They have fucked every man they can at college, and they have even branched out around our neighborhood. I just hope that you three do not corrupt Gwen as she gets older. I will be dying soon and I cannot do anything about what fucking whores you three have come, but I can at least make you three do one thing. I can withhold my estate from you. I have a plan that I have come up with to prove a point. I am going to withhold everything except a $50,000 annual allowance for Ann, from all of you. Only when you carry out these instructions will the remaining part of the estate, currently valued at $35,000,000.00, be released to be shared by all of you as I dictate in an additional amendment to my will. Here’s the plan. Someday soon, Gwen will come home with a man she wants to marry. In order for the remainder of my estate to be issued to you fucking tramps, you will have to each fuck and suck this man before the wedding. One night alone with each of you should do it. The requirement is that you have to give up all three orifices to him. I don’t care what you tell Gwen or if you don’t, but if you do this, to prove my point, the remainder of my estate will be released according to the additional document. If not, then it will automatically go to my favorite charity. In order for this to be considered accomplished, this young man will have to report to my attorney and confirm it. I hope you all rot in hell. Don”
I sat there stunned and read it again. I had never read a letter full of such hate and disgust. It sounded like a bitter, angry old man and was nothing like the man that Gwen had described a few times. “Uh, this is a very strange letter.”
Mrs. Thurman nodded. “Yes, it is. First, I want to say something on our behalf. I never cheated on Don. I have no idea where he got his ideas from, but over the last couple of years he became jealous and saw every man who I talked to as a possible adulterer of mine. Sheila and Gaby are not tramps either. I would imagine that they had a healthy sex life at college because that’s the way things are nowadays. I spoke to them and neither of them understands the comment about the neighborhood. We are not tramps.”
I looked at her and then Gwen. “I have no reason to doubt you. However, this is a very strange situation.” I looked down at my hands. “Mrs. Thurman. I love your daughter more than anything. As soon as we were a steady item I considered that I was only going to be with her. We have been monogamous for a long time. I do not want to hurt her or cheat on her, so I’m having a hard time considering this.”
She looked at me and sighed. “I know. I knew that Gwen would come home with a very nice man.”
“Thank you.”
“You’re welcome. However, I cannot imagine giving up the money that Don accrued over our lifetime. I was a stay at home mother and raised three daughters. I went to all his social events. When I could go back to work, he was making enough that he asked me to stay home. I agreed and continued to support him. I thought I would get his estate after agreeing to that. But since I didn’t, I now find that I cannot support myself or even this house on what I am earning in my job. I was hoping to keep this big house in the family and continue to live in this nice neighborhood and enjoy life, but without the rest of his estate I cannot do it. I know that my daughters each deserve a piece of this, so we talked about it over the last year and a half, to make sure we knew where we stood. We all agree that it’s worth it to do this just this one time for our families.”
“What about contesting it? This is very irregular? Why not contest it and get it thrown out? I cannot imagine any judge upholding something like this.”
Mrs. Thurman looked at her hands, pulling on them, twisting them in nervousness. “I asked a friend who is a lawyer about this. He said we could. However, there is an attachment that I didn’t give you. On it is the list of people he accuses us of cheating and having affairs with. I could probably live with it, but there are very nice, responsible members of the community on there. What happens when this comes out in court? You know that in today’s world it would come out or they would be called to contradict my husband’s allegations. And it would definitely be a juicy news item. These people would be ruined, maybe even their marriages disrupted, by a jealous old man’s fantasies. I cannot think about that. The same is true of my daughters. He names people the same way. I’m sorry, but I won’t do that even if you refuse. I just hope we can convince you to do it.”
When she finished I considered what I had heard.“I’m sorry Mrs. Thurman. I can see you are in a tough spot. I can commiserate with you about this, but there are still dangers besides the personal issues. Can I tell you an old joke?”
She looked puzzled. “Sure.”
“It’s one I heard a long time ago.” I sat forward. “A man was at a bar where he met a very desirable young lady. After a few drinks he leaned over and asked her, ‘Will you have sex with me for a million dollars?’ She looked at him and thought about it, but eventually said yes. He smiled and asked her, ‘Will you have sex with me for a hundred dollars?’ She looked aghast and said, ‘What do you think I am a whore?’ He smiled and said, ‘We’ve already established that, now we’re just bickering over price.’” I sat back and watched Mrs. Thurman.
“So are you saying that this makes us whores?” She was not happy.
“No, I’m saying this may be his way of proving the point that he believes that you are and that this is a dangerous thing we are doing. The final amendment is still unknown to you, right?”
She looked at me carefully. “Right. We can’t see it until it’s time to declare that we have accomplished the first part or decide to protest it.”
“This is a very dangerous thing.” I was worried about what the real goal of such a vicious man would be. Is this really what he wants? He wants them to be whores to prove that they are? Is that really a test?
She came right back at me. “But what choice do we have? If we do not do this before you two are married, we don’t even get a chance at the rest of his estate. I should have some of that, don’t you think?”
“I agree that you should get some of the estate, Mrs.Thurman. I’m sure that I would want it if I was a family member. However, I’m just not sure that I can do this. Gwen?”
Gwen looked up at everyone. She had been particularly quiet sitting there. “John, I love you. I want you to be faithful to me. However, I don’t know how I can say no to my family on this.”
I watched her carefully. She fidgeted and wrung her hands. She was very uncomfortable… as was I. “So if we do this, what’s the plan?”
Mrs. Thurman looked around. “Sheila, Gaby, and I already drew straws long ago to determine the order. I am supposed to go first, then Sheila, and then Gaby. You will sleep with each of us one night for the next three.”
I looked over at Sheila and Gaby. They were also fidgeting and unable to meet my eyes. “Are you two willing to do this, considering you are married?”
Sheila looked up and around. She opened her mouth and hesitated. Finally, she said, “Yeah, I guess so.”
Gaby stared at me until she realized I was waiting for her to answer individually. She was staring at me as she answered. “No choice.”
I went over and kneeled in front of Gwen. “Gwen, you must be absolutely sure that you can handle this. Saying now that you want me to do it and having to remember this for the rest of your life are two different things. Are you going to be able to face the fact that I had sex with the rest of your family?”
“I don’t know. I just think that I have no choice.”
I stood up. “Okay, I’ll do it.”
Everyone visibly relaxed for a moment, and then the mood got tense as everyone realized what was coming. Mrs. Thurman spoke first. “Okay. It’s 8pm. Everyone get to bed and let’s get this over with. John, you can come to my room about 10. Is that okay?”
“Fine.” I watched Gwen and saw her flinch at that. I went to her and took her by the hand. I led her upstairs and into her bedroom. I sat her on the bed and kneeled in front of her. “Any time you change your mind, you let me know, okay?”
She nodded. “I’ll be fine.”
I leaned over and hugged her. “I’m not sure about that, but if we love each other, we’ll get thru this.”
She nodded glumly and looked up at me. “You think so?”
“I know so. I’m not allowed to take that ring back if you remember correctly.”
She smiled a little. “That’s correct.”
We got ready for bed and I put on the pajamas that I had brought. I usually slept in the nude, but made sure I brought them for being at her house. Her mother and family were allowing us to sleep together, which I initially thought was very modern. Now I wondered if that was just because of the situation they were in.
Gwen got quieter and quieter as 10pm approached. She clung to me and we lay there hugging each other. She finally looked up at about two minutes before. “I love you. I want you to take care of them. They are my family and they deserve your respect and love just like me.”
I stared into her eyes. “You are so good to them. I hope they realize what this means to you.”
She buried her head in my shoulder. “I hope so, too.”
She finally pushed me away. “Okay. Go to Mom.”
I stood and she lay there staring at me, a single tear leaking down the side of her face toward me. This made me angry and was fucking with my head. I didn’t know if I should go or not. She gave me a wan smile and “Go. We have to do this.”
I left her and went down to her mother’s room. She was already in bed and waiting. When I entered she looked up and I walked over to her bed. She took a deep breath and patted the bed. I started to climb in.
“Wait!” I looked up at the way she said it. “The pajamas.” She indicated that I was still wearing my pajamas. I knew she wanted me to take them off, but she couldn’t say the words.
I stripped and watched her as my soft dick came into view. She looked up at me and smiled. I climbed in and she cuddled up next to me. She was naked.
She pushed herself up on one elbow and looked at me seriously. “I want to thank you for this. We’ll make this quick and then you can go and comfort Gwen. I know this is hard on both of you.”
I nodded as she leaned in and kissed me. She kissed me and immediately reached for my cock. She was not shy, that’s for sure. We kissed and she fondled me and I finally put my hand up to grasp one of her tits. She moaned and pulled back, closing her eyes. I kept fondling it, running my fingers over the nipple and then lightly squeezing it. She groaned and fell back flat. I looked down as the blankets fell away from her body. Her tits sagged a little, but were nice and full. The nipples had large dark areola, with a short hard nub. They were sensitive, too. I leaned over and took one into my mouth. She groaned and held my head. She kept her eyes closed and I wondered if that was so that she didn’t have to look at me or if she was just trying to enjoy the sex. She suddenly sat up and pushed me back.
“Let me do some oral first. I want to satisfy all the requirements properly. I know that we could just go thru the motions, but we’d better make sure we do it right or I could blow this opportunity… to get the estate.” She added the last part as she thought I might misunderstand what she meant by the opportunity. She dove down and engulfed my dick in a flash. It was my turn to groan. She sucked me only a couple of minutes, licking around the crown and fondling my balls, so that I was soon as hard as I could get. She was quite good at it. She sat back. “Okay, let’s do this in doggy position. You can start in my pussy and then before you cum, move to my ass. I want to get this all over with immediately.”
“Okay.” Was there anything else to say? She knew exactly how she wanted this to go and talked about it so easily I was a little shocked.
She turned over and grabbed something from the nightstand. She handed it to me. “Lube. I haven’t had sex in two years, so my pussy should be fine, but I haven’t had anal in a very long time.” Suddenly she was very frank and open about all this.
Being tight made sense if she was truly as faithful as she said and I had no reason to doubt her. As she got on all fours, I examined the rest of her body. She was actually very attractive and took good care of herself. She had a couple extra pounds, but her shape was good and her ass was fucking hot. It made me think of Gwen and the fact that the genes she got meant she was going to look this good for a long time. I looked down and grabbed my dick and thought that although this was a chore, it was going to be an enjoyable one. I just couldn’t let Gwen know that.
I moved up behind her and she looked over her shoulder. “Remember, go slow. It’s been a long time.” I nodded and she turned again. “Oh, call me Ann. I won’t be able to take you calling me Mrs. Thurman.”
I chuckled. “Okay, Ann,” and I slapped her ass a little.
“Oh, that’s good. I love a little ass-slapping with my sex.”
I obliged her and slapped her other cheek. She grinned as she looked over her shoulder. I moved up behind her and slowly ran the head of my dick around her gash, picking up the lubrication. She groaned and put her head down. I moved my cock forward, working it slowly into her. Damn! She was right, she felt very small and tight. I set myself into position and grabbed her by the hips. I slowly started working more and more of my dick into her. She started moaning and thrusting back. It appeared that she was having no problem enjoying our moment, even though I was engaged to her daughter. I looked down at my dick, hard and enjoying Mrs. Thurman. That fucker always had a mind of its own and pussy was pussy to that one-eyed monster.
“Oh, fuck, it’s been so long.” She groaned and kept pushing back.
Soon I was buried in her and it felt wonderful. I knew that this had to be a quick fuck if I was going to get it into her ass. I started fucking her and she immediately picked up the pace. She was thrusting back against me, ensuring that I buried my dick in her. I slapped her on the ass again and she groaned and increased her speed. I slapped her ass a few more times and less than three or four minutes into fucking she had an orgasm. I managed to hold off and just held still while she calmed down. She eventually did and then turned and looked at me.
“Okay, stud, now take my ass and cum in it. We can be finished by 11pm.”
I smiled and slapped her on the ass. She grinned and I knew that this was going to be an odd relationship in the future.
I picked up the lube that I had put on the bed next to me and without taking my dick out, started working it around her little pink hole. It was also tight, but I managed to work my index finger in and fuck her with it. I added more lube and worked two fingers in.
“Okay, get to the fucking!” She was getting impatient. I had her bent over, my hard dick in her pussy and two fingers in her ass. I think she was horny as hell.
“Okay, Ann. Here we go.” I pulled my fingers out and then extracted my dick. I ran my lubed fingers over my dick to add it to her natural lubrication and lined it up. She put her head down and steadied herself as the head met her asshole. I rolled my hips, working it around her ass at different angles and then started to push. She held her body tightly still, not giving at all. I had never had anal sex, so I had no experience at how hard to push. I kept pushing harder and harder until her ring gave up and let my dick in. When it went in, about three inches went in. I was going to do just the head, but once it slipped in all the pressure I was applying meant it went in pretty quickly before I could stop. Ann groaned.
“Oh, fuck, that’s big. It’s been years since someone had my ass.”
I grinned. “Well, here comes the rest.” I started thrusting and would pull back until I could feel the crown hit the inside of her asshole, and then I would bury it in an additional inch until I was totally fucking her asshole. She was moaning and murmuring how good it felt to do this again, and I knew that I didn’t have long. “Shit, I’m going to cum, Ann.”
“Okay, do it!” Ann started furiously rubbing her clit and I thrust a few more times and she hit her orgasm just before me. She started trembling and her ass was flexing the muscle and that put me over the top.
“Oh, fuck!” I groaned and thrust with each spurt, burying my dick into her and filling her up. I must have done that 10 times, but the last 5 there was no spunk left, just the desire to keep thrusting and feeling that tight ring squeeze my dick.
Finally, I collapsed onto her back, pushing us both flat on the bed. I was laying on her and we were both breathing hard. She turned so she could see part of my face. “That was wonderful. I hope Gwen appreciates you.”
“She does.” I whispered. My dick was slowly shrinking and suddenly it popped out of her ass. “Oh.” It felt so sensitive coming out of her ass.
“Oh, god, I think you filled me up. Get up and let me go to the bathroom.”
I rolled onto my back and closed my eyes. It was very good. I just wondered if it would affect my ability to have sex with Gwen. I didn’t want to have this sudden image of her mother’s ass as I filled it with cum.
I heard the toilet flush and heard Ann pad back into the room. I then felt something warm and wet and opened my eyes. Ann was cleaning up my dick with a warm washcloth. When she finished she put it back in the sink and came back to lie down next to me. She looked directly at me when she spoke. “Thank you for doing this. I know it was for the money, but I really did enjoy it.”
“Me, too, Ann. I hope we can get past this. I still love your daughter.”
Ann smiled. “Of course. Listen. If you want to lie to Gwen, just tell her that we talked, but couldn’t bring ourselves to have sex. It may make it easier for her if she doesn’t think about you having sex with her mother.”
I thought about that. “Maybe, but I don’t want to lie to her. Besides, she will know what I tell the lawyer.”
“I understand,” was all she said as she continued to stare at me. “Are you going to go back now so that we can act like we didn’t do it or that it wasn’t fun?”
I looked at her. She was still very beautiful. “So it was fun?”
She grinned. “You know it was. I loved it. I haven’t had sex since Don got sick.” She looked at me with doe eyes. “Unless you need to confirm that we have fulfilled the requirement.”
Oh, fuck! She wanted me to fuck her again! “No, I think I should get back.”
“Okay. Thanks, lover.”
I looked at her. “Please don’t call me that. It’s not right.”
She looked away. “Sorry.” She looked back and patted me on the arm. “You go and tell Gwen whatever you want. Just as long as you tell the truth to Don’s lawyer.”
“Okay. I’m going to go.”
I got up and quickly dressed and as I left I looked over at Mrs. Thurman. She flashed me a fleshy tit. Fuck!
I got back to Gwen’s room and she was asleep – or so I thought. When I got into bed she turned to me and I could make out her eyes in the dark. She was staring at me. “Is everything okay?”
I turned to her. “Yeah, everything’s fine. Your mother and I talked and talked and we realized we couldn’t do it. I’m going to have to lie to the lawyer, but I would rather do that than hurt you.”
She stared at me. “Thank you. I love you.” She snuggled up to me and relaxed.
I stared at the ceiling. Shit! I had lied to her about this. If it ever came out she would go ballistic. I couldn’t take it back now and she would feel like I was hiding something if she found out after believing that nothing happened. I really was in a fix now. I would just have to deal with it and live with it the rest of my life, because I didn’t want to let this beauty go. But I also had two more women to go, her sisters. This was going to be an interesting but stressful weekend.
to be continued,
by deadeye_76 for Literotica
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