First Time Shared – Penny


I wrote this story by request from my friends Penny and Mark in Australia.

I am Penny and I live “down under” in Australia. I am 54, 5′-10’with a big set of boobs. I am not a BBW but what I would call a lush woman – you know, a few extra pounds but in all the right spots. I am married to my wonderful husband, Mark, who is 63, 6 ft tall and has a stocky build which is all muscle. We own our own business so we can have the freedom to sometimes have a short day or take a day off.


A little over a year ago, Mark told me about one of his fantasies. He wanted to watch me flirt with other men. After a discussion about it, we decided that once a month I would dress up and we would go dancing at a local bar that has live music on Saturday nights. I usually wear low-cut tops to show off my big boobs. My husband always dances the first couple of dances with me then he lets me dance with the other guys present. I flirt with the men and let them feel my butt or brush against my boobs but that is the limit. Most of them push their pelvis against me so that I can feel their hardon. When it is time to go, my husband will dance with me and then we leave. When we get home, my husband is always so turned on that we have a night of fantastic sex. It has livened up our sex life considerably.


On a Saturday a couple of weeks ago, my husband told me at breakfast that he had a surprise for me. I was anxious to know what the surprise was so I pestered him all morning about it. At lunch he decided to tell me what he had planned.

“Tonight I want to do something special. It is something that we most likely will do only once but I really want to try it if you are willing,” he said.

“You have my curiosity peaked so do tell me what you are planning,” I said.

“Tonight I am taking you to the Hilton. I want you to dress upscale but still sexy. While you dance with the men, I want you to select one and spend the night with him at the hotel,” he said.

“Really! You want to do this? I know that you do have some jealousy inside. Can you accept me having sex with someone else?” I asked.

“I have thought about this ever since we started with the flirting thing. I think I can handle it,” he replied.

“Are you going to the room with me to watch?” I asked.

“No! I am not certain that I can handle that yet. I will leave you there and come home. I am not certain how I would react to watching you with someone else just yet,” he explained.

“Exactly how will this work? Have you worked out the details?” I asked.

“Yes, I think so. We both will dress up and have dinner at the hotel. Afterward, we will go the bar/dancing area. I want you to dance with the men there and if any one of them would excite you, then I want you to accompany him to his room for the night. When I see you leave the bar area, then I will drive home. I want you to spend the night if it works out that way. He will buy you breakfast and then you will take a taxi home to me. If during or after sex, you want to come home rather than spend the night, then dress and catch a taxi home,” he said.

“If there are no men of interest there, then what?” I asked.

“Then we will just come home with a full stomach,” he said.

“What will you get out of this?” I asked.

“When you get home, I want you to tell me exactly in detail what he did with you and we will do exactly the same thing. I will be fiercely horny so we may have sex several times,” he said.

“My God, that sounds exciting. I am thrilled to try it but if you have problems with it, we will just come home,” I offered.

“Of course. I know we do the same things every time we make love so I thought if we could repeat what the man does with you, it could liven up our sex life a bit,” he said.

“Honey, it is almost noon so I better fix my hair, take a shower and start figuring out what to wear so that we can get to the hotel for dinner,” I said.

I ran upstairs and started going through my closet looking for attire to wear tonight. I decided on a simple black dress that had a fairly low-cut front to show off my boobs. I put it on and went downstairs to show my husband.

“That is the perfect dress but I think you need to shorten it some. I want you to show off your beautiful thighs a bit more,” he said.

I pulled up the skirt a little at a time until he said “that’s it”. It was at least 4 inches shorter. I took it upstairs and using my sewing machine I raised the hem about 4 inches. I put it on and modeled it in front of the mirror. I see what my husband is trying to accomplish. The new length does show off my thick thighs. Actually, I think I look very attractive. I know that with this dress I can get some attention. I went downstairs and modeled it for my husband.

“That is exactly what I wanted for tonight. You will attract a lot of attention tonight,” he said.

I went back upstairs and put the dress on the bed. I went into the bathroom and undressed. I looked at myself in the mirror. I don’t look bad for 54 years old. I did notice that gaziantep escort my black pubic hair was fairly long and a bit unkempt. I took a comb and my husband’s electric trimmer and I shortened the hair to about 1/4 inch long. I then took my razor and trimmed the perimeter so make a smaller triangle. That looked good enough to eat I thought. I jumped into the shower and cleaned up everything especially the pubic area. I dried off and went to my dresser for underwear. I picked out my sexiest bra which was my black one – 40DD. For a girl of my size I wore cotton bikini panties. I then put on my makeup for the evening. When I went back to the bedroom for my dress, I saw my husband putting on his best dark suit. He even had a tie on. Wow! He is so handsome! I finished dressing and put on some of my favorite perfume with a dab down by my pubic area.


We drove 45 minutes to the Hilton and parked our car. My husband had made dinner reservations so we were seated immediately. Mark ordered a steak and I had the lobster dinner. My husband reviewed the rules for the night with me.

“I will stay here until you give me the sign that you are headed upstairs. Do a hand wave but below your shoulders so that it is less noticeable. That is my sign to leave. If you get into trouble on the dance floor or at the bar, wave your hand above your head and I will be there in a flash. If you get into trouble up in his room, call my cell phone as I might not be home yet and I can turn around and come back for you. I am going over to talk to the bartender and I will tip him to make your drinks are watered down. I want you in control and not drunk. In the room you have complete freedom but I would ask you not to do anal. I would like to keep that special just for us and only on special occasions. Any questions?” he said.

“No, I have no questions. Are you sure that you are OK with this?” I asked him.

“Yes, I think when I leave I will think about fucking you when you come home rather than worrying about what you will be doing tonight,” he answered.

We finished our dinner and then moved to the bar area. We sat at a table away from the dance floor so that Mark would not stand out while he watched over me. He went to the bar and talked with the bartender and I saw my husband slip him some money. He returned with two drinks. We both sat watching the people in the bar. It was mostly couples of various ages but there was one man at the end of the bar drinking alone. He was quite handsome and had blonde hair and a slight beard that was neatly trimmed very short. I thought he looked nice and he dressed very neatly. He might be a possibility for this evening. I pushed my drink over to Mark and I headed for the bar. I sat down on the stool next to him.

“Mind if I sit next to you?” I asked.

“No, not at all. Are you alone?” he asked.

“No, my husband is sitting over at the table by the far wall. He isn’t feeling very well and he said he was going up to our room and go to sleep. It is too early for me to go to bed so I thought I would sit at the bar and have a drink. On my way over to the bar, I thought I would sit with you and we could talk,” I said.

“It is too bad that your husband is ill. Do you think it was something he ate?” he asked.

“Not really. He has a sensitive stomach. It happens often but I didn’t want it to spoil the evening. I decided to sit by you because everyone else here are couples. I thought I could have my drink and maybe talk with you if you don’t mind,” I said.

“Not at all. I could use the diversion to keep me from thinking about work and missing my wife,” he said.

“Where are you from?” I asked.

“I am from Colorado in the US. I am here on business for two weeks,” he said.

“I am Penny and I live here in Australia,” I said.

“My name is Jim,” he said.

“So tell me what you are doing all this way from Colorado?” I asked.

‘Well, I am an engineer and I have been hired by the US Dept. of Energy to come here to witness some low-level nuclear weapons that your government is testing someplace way out in the desert. Other than that, I can’t discuss it as it is classified,” I said.

We talked about things that he should see before he leaves Australia. The band started playing some slow songs so I asked him to dance with me. I found that he was quite a good dancer and it was fun dancing with him. He did not try to feel my butt nor do anything like the guys do at the bar that we usually go to. However, I did catch him several times looking down at my boobs.

“I notice that you like looking at them. Do you like them?” I asked.

He turned red and tried to look me in the eyes.

“I am sorry, but it is just that I have never seen any … that big. I was trying to imagine what the areolas and nipples look like,” Jim said.

“I am not shy and I love my breasts. Would you like me to show you my breasts?” I asked.

“I am sorry. I should be more of a gentleman. My curiosity does get the best of me sometimes,” he said looking away.

“Take me up to your room and I will not only show them to you but I will let you touch them,” I said.

“Look, I am married and I should be good,” he said.

“I am married too. My husband is still sitting over there drinking his ginger ale for his stomach. I will wave to him to let him know that I am OK,” I said. And I waved low to my husband. We both saw him nod and leave the bar.

“Good, he is going to bed. He takes two sleeping pills when he is like this and he won’t wake up before noon tomorrow. I have nothing to do and I am not ready to go to sleep so let’s go to your room,” I said.

“Yes, of course. I am in 314,” he said and we left the bar.

“As we rode up in the elevator, he put his arm around my waist. He escorted me to his doorway. He used his keycard and opened the door for me. He had a suite with a sitting room and a separate bedroom. The bathroom was attached to the bedroom.

“Let me go to the bathroom and freshen up. I will meet you in the bedroom if that is all right with you,” I said.

“Yes. Sure. The bathroom is off the bedroom,” he said.

I ran in and peed. Then I washed up my pubic region with a washcloth and dried off with a hand towel. I was undecided whether to return to the bedroom dressed or nude. I decide to go in dressed because this guy was shy.

I walked into the bedroom and Jim was standing by the bed removing his shirt.

“I really have never been unfaithful to my wife before. I had quite a few ladies before I was married. I guess I am somewhat uncertain what we are doing,” Jim said.

“Only one man has ever been in my pussy and that is my husband. This is the first time I have ever done this too. We are a long way from Colorado so no one will ever know what we do tonight unless you tell them,” I said.

“Will you tell your husband?” he asked.

“If he asks me what I did tonight, I won’t lie to him,” I said.

“I suggest that we undress and that we crawl into bed. We will play it by ear and just see what happens naturally,” I said.

“I know that I seem uncertain and shy but I am not really. I have a penis that is different from most men. It has caused me a lot of teasing and bullying when I was growing up. Consequently, I am not willing to be undressed in front of people. Tonight I guess I am somewhat concerned about exposing myself to you,” Jim said.

I had my dress off so I was standing there with just my bra and panties on. I took off my bra and release the girls. Jim was down to just his shorts.

“You said you wanted to see my nipples so here they are,” I said.

He walked over to me and he used his hands to cup my breasts.

“These are unbelievably large. Your areolas and nipples look very … sexy and they are in proportion to your large breasts. I guess the child in me wants to lick and suck them,’ he said.

“Please go ahead. The nipples are very sensitive. I can sometimes even have an orgasm just from my nipples,” I said.

He took what I said as permission to go ahead. He bent over and sucked my right nipple into his mouth. He was very gentle and did some fantastic things with his tongue on my nipple. I moaned and almost had an orgasm from his efforts. It became too sensitive so I lifted his head up and I kissed him. My lips were partially open and I pushed my tongue through and searched for his tongue. He pressed his body tightly against mine and we kissed several times. I could feel a hardon pressing against my tummy.

I broke the kiss and leaned back and said, “Show me this unusual penis and I promise not to laugh,” I said.

Jim hesitated for a minute then pushed his shorts down. When he straightened up I saw a huge cock that was hard as a rock and standing straight up. All his pubic hair was shaved off. I moved toward him and I reached down and gripped his cock with my hand. It felt as hard as if it were made of iron. He was longer than my husband and thicker. The head was the widest part and it turned red as I squeezed the shaft.

“Lay on the bed. I want to play with this,” I said. “I see that you like to shave you privates.”

“I was on the swim team in college. We had to shave our whole body once a week. My wife likes me hairless so she does the shaving for me. I think it looks neat,” I said.

Jim laid down on the king-size bed and his cock was lying on his stomach. It seemed quite long and covered his belly button. I kneeled on the bed beside him and took his cock in both hands. I could wrap both hands around it and the head was sticking up above my hands. I immediate tried to take him into my mouth but the head was so big that it was all I could fit in. I used my tongue around the head and then started jacking the shaft up and down with one hand. I heard him groaning so I knew that I was doing what he needed.

“God! You are great! I haven’t had sex in over a week so I won’t last very long especially with your talented tongue,” Jim said.

I have never seen or played with a cock this big before. I wanted to see if I could get him to have an orgasm. I kept up with my tongue and hand job until I felt him arch his back and he pushed his pelvis against my face. He had a loud orgasm that seemed to last for a minute or more. I felt him shoot 4 strong jets of semen into my mouth. I sucked on him fairly hard to get the last of his semen. I had to swallow several times to handle it all.

“That was wonderful! I warned you that it would not take me very long,” Jim said.

“Believe me. It was just as good for me as well. I have only ever given head to my husband so it was nice to try a different cock,” I said.

I laid down beside him and we talked about sex for a few minutes.

“Before we go any farther I need to tell you that I do not have any condoms with me,” he said.

“Not to worry. I had a complete hysterectomy several years ago,” I replied.

“I think it is my turn to give you some oral sex,” he said.

He spread my legs apart and positioned himself so that his mouth was right over my clit. He used his fingers to part my lips and I felt him licking the inside of the lips. Then he used his tongue around the opening of my vagina. Every second or third time around, he would stick his tongue as far as he could into my vagina. My husband had never done that. He then moved up to my clit and I moaned loudly as he sucked it into his mouth. He was really stimulating my clit. I felt him inset what felt like two fingers into my vagina. He started working them in and out. That pushed me over the edge and I had a small orgasm but it felt really great. He didn’t stop when I had the orgasm but he did stop the in-and-out with his fingers. I felt him insert them as far as he could. Then he curved them upward and started searching for my G spot. When he found it my whole body jumped. It wasn’t long before I started another orgasm. This guy is really good with his mouth and fingers. This was a huge orgasm for me – bigger than most that I have with my husband. I arched my back and I squeezed his head with my thighs. I screamed softly and when it had passed. I fell flat on the bed.

Jim looked up from between my legs and said, “That sounded like a good orgasm. If it wasn’t you can have your money back.” And he chuckled to himself.

“That was one of the best I have ever had. You are very good at giving oral,” I said.

“I learned to give oral so that I could satisfy a woman when on a date. That way I didn’t get turned down over the size of my dick,” he said.

“Really? Women actually refused sex with you because of the size of your cock?” I asked.

“Yes. It can be pretty humiliating in the bedroom when I undress and the woman screams and throws me out of her apartment,” he explained.

“If you are ready again, I would like you to try it putting that big cock in me,” I said.

“Yes, I am still hard,” he answered.

Jim moved up farther between my legs until we were face-to-face. He laid some of his weight on me and I felt him moving the head of his dick between my pussy lips. I felt him moving the head around inside my lips and all around the vagina opening. I guess he was trying to get it wet. Then I felt the head enter my vagina. It was larger than my husband’s and it filled me up. He stopped and let me get used to it.

“Wow! You are bigger than what I am used to,” I said.

“I will enter slowly and allow you to adjust to my dick,” he said.

I felt him push a little deeper then stop. He continued doing this until he was fully inside of me. I felt full and I could tell that my vagina was stretching to accommodate him. We lay there neither of us moving. I have to admit, I was enjoying having him inside of me.

He began to slowly stroke in and out of me. He never stroked really fast like some of the men I have seen in porn movies. He kept up a slow in and out. The feeling was intense and he was driving me crazy. I wanted him to speed up so I could have and orgasm. Finally I could not stand it anymore and I had a huge orgasm. It felt really good and I let everyone know it in the rooms around us. He continued stroking in and out and I knew that he had not cum yet.

“Would you like to try another position?” I asked.

“Would you mind doing the doggy position. I would like to cum in you that way,” he said.

He crawled off me and I rolled over and got up on my hands and knees. He moved around behind me and put his hands on my hips. I felt the head of his cock spread my lips and then it was back inside of me. My body shivered as he entered me. I honestly had never felt anything like this in sex before. He started to stroke in and out but a little faster than before.

After a couple of minutes stroking, he said to me, “Would you mind slowly lying down. It is my favorite position.”

I slowly lowered myself until I was lying flat on the bed. He followed me down so that his cock was still inside of me. He put most of his weight on my back and started stroking again. He started going a little faster so I knew that he must be getting ready to cum. Suddenly he came all the way out and he said “Opps”. I felt him reach for his cock to re-insert it. I felt the head slide between my butt cheeks and he gave hard push with his hips. However, his aim was off and the head pushed inside of my ass.

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