“Yes, I will help you, on one condition.”
“And just what condition would that be?” Now it was my turn to be curious.
“That you sleep with me first. Is that acceptable to you?” Jessie asked a bit nervously.
“Why don’t you join me and I’ll give you my answer.”
Jessie started to take off her clothes, and then stopped.
“I have a better idea. Why don’t you come here and undress me yourself. I know that you enjoyed watching us sunning ourselves and I’m sure you are eager to see what little was hidden by my bikini.” Jessie stated with a knowing smile.
“I wouldn’t mind doing that at all.” I replied as I started back toward the edge of the pool.
Jessie stepped back as I reached the edge and I could tell that she was nervous, but trying hard not to show it. She was staring at my 8 inch long cock which was extremely hard from the constant torture of being around these four women and the anticipation of fucking this gorgeous little red head. I slowly approached her so that, hopefully, she wouldn’t change her mind. I put my arms around her and pulled her toward me so that my cock was sandwiched between us.
“I’m game if you are.” I said with a devilish grin.
She just smiled and put her arms around me. I leaned forward and kissed her lightly on the lips, slowly adding pressure to the kisses until she opened her mouth. After a couple minutes of kissing, I brought my hands down her back to her firm little ass and squeezed, causing her to moan. I slid my left hand up her side to the edge of her right breast and gently massaged it, feeling her nipple get harder under my palm. As her breathing got faster, she started to rub herself against me. The pressure she was putting on my straining cock was exquisite torture for me. I stepped back just a little and taking her right hand in my left, guided it to my aching cock. She acted rather shy about touching me and I had an interesting thought. Could she be a virgin too? Just the thought of it almost made me shoot my load.
“Jessie, I need to know something. Are you still a virgin?”
“Yes” she replied in a barely audible whisper. “But I don’t want to stay that way any longer. I don’t want to be the last virgin on this island.”
“I thought that you might be and I’m glad that you told me. Your first time should be special, because you will never forget it. I will do what I can to make it pleasant for you, but you have to know that there will likely be some pain at first. This pain is normal. Are you ready to become a woman Jessie?”
“Yes I am. Thank you for your concern.”
I returned to kissing her and fondling her breasts, making sure that she was thoroughly aroused. She stiffened up a little as I started removing her shirt. She must have thought a lot about this because she wasn’t wearing anything under her short outfit. Her young, B cup, breasts were as perfect as I had imagined. When I knelt down and undid her shorts, I thought she was going to change her mind. I thought my cock was going to explode as her virgin pussy came into view with its sparse covering of red pubic hair.
“You are absolutely beautiful Jessie.” I told her hoarsely as I leaned forward and planted a kiss one her pubic mound as she stepped out of her shorts. I stood back up and continued kissing her. I slid my right hand down her back and squeezed her bare ass cheek, causing her to push herself toward me. She let out a load moan as I slid my hand over her bush and touched her virgin pussy for the first time. She was already rather wet with anticipation. I ran my fingers up and down her slit, spreading her moisture along her slit and my fingers. I was almost shaking with anticipation myself and I slowly slipped a finger up into her wet canal. She must have been more aroused than I had expected because this brought on her first orgasm and her knees tried to buckle from the sensations coursing through her. I gently laid her down on the still warm grass and kissed her some more while she came back down to earth. She was smiling as I moved down and took one stiff nipple into my mouth and sucked gently, then switched to the other nipple while stroking my finger in and out of her, now very wet, pussy. After a little while, I carefully slipped a second finger into her, causing more moaning. I continued to stroke her until I was fairly sure that she was loosened up enough that I wouldn’t hurt her when I entered her with my cock. Jessie looked uncertain when I moved down her body and positioned my head between her legs. Her first reaction was to pull her legs together, but she opened them back up at my gentle urging. She never took her eyes off me as I lowered my mouth to her inviting little snatch. It looked as though Jessie had been hit by lightning when my tongue brushed across her hard little clit, bringing on another orgasm. I decided that she was about as ready as she was going to get and I wasn’t sure how much longer I could wait. I moved up between her legs and very gently guided my painfully erect cock to her waiting pussy. She was still so tight that I had to enter her slowly. I felt my cock being squeezed so much that I wasn’t sure I would be able to fit. After a couple inches, I felt the resistance of her hymen and stopped pushing. I slowly stroked in and out a few time to make sure that she was ready and that my cock was well lubed before plunging myself all the way to the hilt, piercing her hymen. As I hit bottom, Jessie let out a strangled gasp followed by a deep moan that I could feel through my cock. I held still for about a minute to allow her to get used to being filled like this. Granted my cock isn’t the largest out there, but it is a lot more than she had held before. When Jessie had composed herself, I slowly withdrew most of the way from her pleasurable depths before sinking all the way in again. It only took a couple strokes before she was matching my motions and approaching another orgasm. I wanted to cum in her but I didn’t want to get her pregnant either, so I held off until she started to cum and then withdrew and shot my load of cum all over her chest. That was the most powerful orgasm that I had had in a long time, but I was also looking forward to initiating Liana.
“That was more incredible than I had imagined. Is it always like that?”
“No, there is only one first time. You will probably be a little sore this time, but from now on, it will just feel good. I hope that I was easy enough on you that it didn’t hurt too much.” I said with obvious concern.
“You were wonderful and it didn’t hurt much at all. I am a little sore though. When do you want to help Liana with her virginity? If you don’t mind, I would like you to wait a couple days so I won’t be so sore and maybe we could show her what she is missing together.”
“That sounds like a plan to me. Let me know when you feel up to it and I will let Liana know.”
We rested for a little bit and then went for a swim to clean up. The blood on her legs scared her a little, but she knew it was normal for a virgin to bleed when her hymen was ruptured. When we were done, we spent a couple minutes kissing before getting dressed and returning to camp. |