Andrea and Jessie were sitting beside a small fire. They looked up at us as we came out of the trees.
“And just what have you three been up to?” Andrea asked with a smirk.
“I can tell that it will be very difficult to keep secrets around here. So, if you must know, Liana asked me to assist her with something and I asked Mandy to help me.” I didn’t figure that the vague answer was going to be accepted, but I thought discretion was called for. If Liana wanted to tell them what we did, it was up to her.
“OK Liana, spill the beans.” Jessie chimed in.
“Oh all right. I told Brian that I didn’t want to be a virgin any more. He said that having one of you there might help me to relax. I was very nervous, but after seeing him with Mandy, I couldn’t wait to find out for myself.” Liana stated rather matter-of-factly.
“I thought it might have been something like that, but I didn’t realize that you were still a virgin.” Andrea said.
“I’ve known about that for quite a while. So what made you decide on Mandy and not one of us?” Jessie wanted to know.
“Well, I knew you were also a virgin and I didn’t know if you would want to help or not. As for you Andrea, I didn’t think you would agree once you knew what we wanted. I’m sorry if I misjudged either of you.” Liana told them.
“Now that everybody knows where we were, I have to ask, what happens now?” I asked the four of them.
“I am a little frightened about sex, and I thank you for not putting me on the spot.” Jessie told Liana. “However, I wouldn’t mind loosing my virginity, especially to someone like Brian.” She said smiling at me.
“He was just great. You won’t be sorry. I have to admit, I am a little sore though.” Liana told Jessie.
“I’m not sure I understand something.” Andrea commented. “Just how did you help Mandy?”
Mandy was blushing as she replied. “I let him fuck me first with Liana watching. Then when it was her turn, I helped her to relax.”
“Exactly how did you do that?” Jessie wanted to know.
“Well, Jess, I let her explore my body and then I explored hers. We ate each other to a wonderful orgasm and them Brian popped Liana’s cherry. Afterward, I had him fuck me again, really hard this time. I’ve never been fucked that good before. I don’t know how Brian feels about it, but I can’t wait for more.”
“Oh my god!” Andrea exclaimed. “I didn’t know that you were bisexual Mandy!”
“Liana and I aren’t bisexuals. That was the first time I had ever tried anything like that. I have to admit though; I think I could learn to enjoy it.” Mandy was no longer blushing and appeared to be daring anyone to challenge her.
“Tonight was a first for me as well.” I told them to break up the tension. “I had never been with two women before. I know that I would enjoy more of that.”
Everyone laughed and the tension that had been building vanished. I wouldn’t have chosen to come out in the open so soon about our little adventure, but now that it was out, I wasn’t sorry.
“Maybe only building one bed wasn’t such a bad idea after all.” Jessie commented “Since we are all being so candid with each other, why don’t we all head to bed and get comfortable. We all can decide on where we go from here in the morning.”
Jessie’s suggestion was greeted by a round of approval. The five of us headed into the hut and, by mutual consent, stripped down to our birthday suits before crawling into the one large bed. I was in the middle with Jessie on one side and Andrea on the other. Liana and Mandy felt a little guilty about not sharing me earlier and wanted to make up for it. I didn’t think it would be possible for me to get hard again tonight, but Jessie didn’t want to wait any longer. The four girls took turns fondling my cock and balls. When my cock started to rise, they took turns sucking and licking it. Mandy went so far as to suck my balls into her mouth, which sent a shock through me and brought my cock to attention. With everybody watching and encouraging her, Jessie straddled my chest and lowered her pussy to my mouth. Jessie let out a load moan when I started licking my way up to her clit.
“I love to have my pussy eaten. Eat me good.” She prompted me.
I moved up and sucked her clit into my mouth bringing on her orgasm. I continued to administer licks and kisses to her pussy until she came back down. Reaching up, I guided her to move back and, while Andrea held my cock, gently pushed her cunt down on my cock, stopping when I felt resistance and just waiting for her to make the next move. She sat there for a moment or two with her eyes closed before starting to move on my shaft. I looked over and saw Andrea fingering herself as she watched the scene unfolding in front of her. Liana and Mandy were each sucking on one of Jessie’s breasts. Almost as one, they reached up to her shoulders and brought her down hard. She let out a startled scream, which was followed by a very contented moan. Jessie seemed frozen, sitting there with my thick 8 inches of cock buried deep inside her. Gradually she started to rock back and forth. I was almost worn out from my previous activity and was glad to let her set the pace. Soon she was bucking hard and I knew she was ready to cum, but I had cum so many times already that I wasn’t in any danger of losing it yet. Jessie had what must have been and earth shattering orgasm, because she passed out on top of me. I was really concerned, until I realized what had happened. It was another first. Liana and Mandy helped her off of me and into the covers so she wouldn’t get cold.
“Now I would say that it is my turn.” Andrea stated. “How do you want me?”
“I want you any way that you will allow.” I replied. “The question is how do you want it?”
“A friend of my sister told me about something she likes and I think I might like to try it.”
“And just what would that be?” My curiosity was evident as I asked.
“Jamie told me that when she is on her period and her boyfriend wants to fuck, she lets him fuck her in the ass. I was shocked when she told me that, but after a few experiments with a dildo, I found that something up my ass kind of turned me on. From the sound of it, this has been a night of firsts for about everyone, so would you mind fucking my ass tonight?” Andrea’s voice was barely more than a whisper as she asked.
“I can’t say that I have ever really thought about doing that, but if that is how you want to make tonight special, I don’t see how I can refuse. After all, Liana and Jessie both got their cherries popped and Mandy said that she got the best fuck of her young life. As for me, I get the pleasure of fucking four beautiful, young women who I have watched with almost unbearable desire for the last year. I just have to know, are you really sure that this is what you want?”
“I’ve never had anal sex with a guy before, but yes I am sure and I am glad that my first experience will be with you.” Andrea answered honestly.
“Since you are sure, then I agree. I will take your anal virginity, but not until I am sure that you are ready. Now, come here and relax.” I told her as I took her in my arms and kissed her on the mouth. By now, Jessie had waked up and she, Liana, and Mandy were cuddling in the bed while watching Andrea and I. I had seen the looks of shock on their faces at Andrea’s suggestion, but her back was toward them. I almost laughed at the stunned looks I got when I agreed, but fortunately no one said anything. As we kissed and caressed each other, I could feel the tension go out of Andrea. I ran my hand up her inner thigh and she opened her legs, allowing me to touch her pussy. I slipped a couple fingers up inside her to coat them with her juices, which were flowing freely. I would give her pussy a couple deep strokes and withdraw my fingers so that I could spread her juices around her puckered little anus. After a couple times of doing this, I slipped a finger into her ass. Andrea was squirming on my finger as I worked it in deeper and then withdrew. I went back to fingering her pussy to get more lubricant. I knew that she would need plenty if I was going to be able to fuck her without hurting her. I continued this process while kissing her lips, neck and breasts. I think our audience was getting into it as much as we were. After several minutes, I added a second finger to her virgin ass and worked them in as deep as I could. After about 15 minutes of this, I figured that she was about as ready as she was going to get, but first I needed to lubricate my cock.
I gently rolled Andrea onto her back and moved up between her legs. The other three girls moved closer, so that they could see. Jessie even started rubbing Andrea’s breasts and pinching her nipples. I lined my cock up and smoothly entered Andrea’s pussy and started slowly sawing in and out. Every few strokes, I would remove my cock and rub it across her asshole to help spread more of her juices and then return it to her waiting pussy. I could tell that she was extremely aroused and decided it was time.
“Last chance; you can still change your mind.” I told Andrea as I positioned the head of my cock against the puckered ring of her asshole.
“Do it. Do it now.” Andrea cried, nearly breathless with anticipation.
I gently started pressing my cock against her asshole. It took a little pressure before my head popped in. I wasn’t sure how much more I could take, but if her anal muscles continued to spasm, I was going to lose it. Andrea’s whole body went rigid as I entered, but taking a deep breath, she forced herself to relax.
“Are you alright?” I asked. I wanted her reassurance that she wanted me to continue.
“I’m fine now. It’s just that you feel so big. Please don’t stop, I really want this.”
“OK, I’ll take it slow. Let me know if you change your mind and want to stop.”
I eased about another inch into her and hesitated again to let her adjust. I withdrew almost all the way before sliding in again. Andrea didn’t seem to be having any problem, so I slid in as far as I could. Her only reaction was to inhale sharply and then moan long and loud. Looking down, I could see my cock stretching her asshole and I was amazed that it actually fit. As I started thrusting gently in and out, Andrea started shifting her hips to meet me and soon I was slamming into her fairly hard. The other girls had stopped what they were doing to watch.
“Come on, fuck me hard!” Andrea moaned. I took that to mean that she definitely liked what was happening, so I really started slamming into her and when I felt my orgasm approaching, I didn’t even slow down. I just kept hammering away at her ass until I filled her bowels with my hot sticky semen. I gave her a couple more thrusts and then collapsed, completely spent, on top of her. I felt my cock starting to slip out of her ass and rolled off of her. Andrea just lay there.
“Are you ok Andrea?” I was concerned that maybe I had hurt her.
“Yes. That was incredible. I don’t know if I can even move, or if I even want to.” Andrea said with an expression of complete bliss. I looked down at her spread legs and could see my cum dribbling out of her dilated asshole. I took Andrea in my arms and moved her to the bed, where she was surrounded by the other girls. I went to the pool and washed myself off. I could see some bloodstains on my cock. It was an interesting night to say the least. I wondered how long we would be stuck on this island and what would happen if we ever made it back home. Would we still be close or would we drift apart. I decided that I would just make the best of our situation and let the future take care of itself. I relieved myself and headed back inside and fell asleep surrounded by my four gorgeous women.
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