Jessie's First Time
Day after Peep Show 2 Please read it first.
Sorry, this is long but I think you will enjoy reading my experience with Jessie at the lake.
I woke to find myself spooning and hugging Jessie. This is not unusual since we always shared my bed when she spent the night, which were most weekends. I lifted my head and peered over to see if Jessie was awake; she was still asleep. It was then that I noticed not only was I hugging Jessie, but my hand was cupped around her left breast and her hand was holding mine in place! I laid my head back onto my pillow still holding Jessie tight to me.
Realizing I was holding Jessie’s left breast, sent a warm chill ending in a slight twitching between my legs. I could feel a dampness forming between my lips as I carefully and slowly rolled on to my back. Jessie suddenly rolled over onto her right side facing me settling in with her head on my chest. In a soft mumbling voice Jessie asked if I was awake.
“Abs, you awake?”
“Yes, Jess. I’ve been awake for a little while. Did I wake you when I rolled over? I’m sorry if I did, I tried not to wake you.”
“No, I’ve been awake for a while too. I was trying to lie still so I wouldn’t wake you.”
We giggled softly about our concern for each other. We had been friends for few years by this time but you would have thought we grew up together. Most times we didn’t have to speak a word, we always seemed to know what each other were thinking or feeling.
“Jess, I realized when I woke I was holding you… I mean, I was holding your breast.”
“It’s okay Abs… I was sort of holding your hand there. I’m not sure I might have moved it there while I was dreaming last night. I’m sorry; I hope it didn’t freak you out or anything.”
“No, it didn’t freak me out. Actually, it…. What did you mean by ‘or anything’?” I asked.
“What? Oh, I don’t know. I just… I don’t know. It felt…”
“Good?” I finished her sentence for her.
Jessie looked over at me, staring, searching in my eyes for my reaction. “Yeah, it felt good. I mean to wake up with you holding me like that. It felt different than before when you’ve held me. Don’t be mad ok?”
I smiled a little at Jessie, then gently pushed her back onto her left side, slide over as close as I could and then wrapped my arm around pulling her into me tighter. My hand came to rest just below her left breast with the underside of it slightly resting against the top of my thumb. “It did feel good.” I whispered in her ear. I felt her shift her body, snuggling in closer against me as we quietly talked about nothing in particular. My breasts were now pushed tight against Jessie’s back and I could feel my nipples getting harder.
I shifted a little in the bed, my arm to move involuntarily forcing my hand upward. Jessie suddenly inhaled deeply, her body stiffing as my hand came to rest cupping the underside of her breast. She slowly exhaled but her body remained rigid. I started to move my hand back down just as Jessie shifted her weight, moving her body slightly but made my hand move upward again this time covering her breast, coming to rest with her nipple in the palm of my hand. I heard her gasp and then let out a soft moan. My arm flexed attempting to move as I was about to apologize. She felt my arm about to move so she quickly covered my hand with hers.
I leaned over to see her face. Her eyes were closed and she wore a slight smile.
Jessie whispered, “Don’t. It’s okay. It feels good.”
I leaned in and kissed her cheek. Smiling, I could think of only one response. “Yeah it does.”
We had fallen back to sleep for about an hour. My brother came stomping in the room trying to walk as loud as he could and in a rather loud voice he announced his arrival.
“I hope I didn’t wake you two. I tried to be as quiet as I could.” He wasn’t fooling anyone and all of us knew it.
“If that was quiet, I’d hate to hear you be loud… You know you really aren’t that quiet, especially if you were doing something you didn’t want anyone else to know.”
Jessie rolled over looking at me with wide eyes. We both started to laugh. My brother just stood there with a dumb look on his face like “What are you talking about?”
“You’re weird Abs. Time to get up, Mom has breakfast going and is planning on taking us all to the lake. And yes, Jessie, that means you get to tag along.”
The comment to Jessie was just a jab. Jon was always giving Jessie and me a hard time. Jessie didn’t really “tag along”, she was always invited to everywhere with us and she knew it. In fact, this weekend she was invited to go with us and spend some time at our cabin at Lake Chelan.
After eating breakfast we loaded up the car and headed to Lake Chelan. Mom was driving, Jon rode shotgun and Jessie and I sat in the back seat. It was about a three hour drive but time went by quickly as all of us chatted up a storm. I think we were all excited about the trip; Mom hadn’t had a chance to take a break from work so it was the first time in months since we were able to take a trip as a family.
We quickly unloaded the car, put things away and headed to the backyard to soak up some sun. As Jessie and I were setting up the lounge chairs we heard a loud splash. Jon was already in the water. Our cabin is far enough up the lake there isn’t a lot of boat traffic and the nearest neighbor is actually a state park about another mile up the road. The cabin is secluded, surrounded by forest service land, not other cabins. It wasn’t long before Jessie and I were kicked back in the lounge chairs, our naked bodies soaking up the rays and the warmth of the sun. Mom came out shortly after with iced tea and then joined lying out in the sun.
As always, Mom had to have her little talk with Jessie. Jessie’s family are not nudists, however Jessie is, so she fits in around my family just great. But Mom always seems to find a way to mix in a conversation regarding nudism and making sure Jessie is comfortable with it and knows she doesn’t have to participate. In fact if it made her uncomfortable we would not go naked around her. This is at the point where Jessie and I both normally laugh because we know she is cool with it and enjoys the opportunity to be a nudist.
“Mrs. Turner, honestly, I am fine with the whole nudist deal. I really enjoy it. I wish my parents were into it, but I can’t let that stop me.” Jessie said.
“Mom, Jessie has been around for what three years now? If she didn’t like it, she wouldn’t do it and probably wouldn’t be around the house all the time.” I said trying to assure my mom.
“I know, I just want to make sure that at anytime if she changes her mind, she can just tell us.” Mom replied. “But on the other hand, if you are good with all of this, why do you seem a little nervous right now?”
I did notice that Jessie was fidgeting a little when Mom had come out and joined us. Jessie wasn’t trying to hide or cover up, she just seemed, well, a little nervous.
“Well, I guess it’s hard getting use to the fact that you are walking around naked too. I mean, it’s not like it’s the first time, but to just kick back with us like this seems weird in a way.” Jessie said.
“Is there something about me that bothers you?” Mom asked.
“Oh no, no no! Not at all.” Exclaimed Jessie as she sat up to face mom. “You’re a beautiful woman and you treat me as a good friend… More like family. I guess it’s because you’re a parent and my parents would flip if they saw me lying out in the nude.”
Mom smiled and laughed a little. “You are so sweet, thank you for saying I’m beautiful, but that’s not what I was worried about. But I do understand the part about me being a parent. Maybe if you stopped call me ‘Mrs. Turner’, you wouldn’t feel as nervous with me being around. And Jessie, you are like family, to all of us.”
Jessie let out a deep breath, stood up, walked over to mom, gave her a big hug and said, “Thank you Cynthia.”
As the two released their hug, they looked at each and at the same time said, “That sounded weird didn’t?”
They both laughed and agreed. Jessie looked at her and said with a smile, “Thanks Mom!” Jessie then gave my mom another hug and a kiss on the cheek.
As Jessie walked back over to her lounge chair, mom smiled and said she liked the sounds of that better and would be honored to be called ‘mom’ so long as she was okay with it.
It was almost sunset, Jon had promised mom a boat ride during sunset (which she has always adored since as long as I could remember) so off they went for a sunset boat ride. Jessie and I drew names to make dinner for everyone so we headed in to get cleaned up before starting dinner.
We grabbed towels and headed for the upstairs bathroom to shower. Normally Jessie and I chat while the other showers. Jessie was first in but in the middle of her shower I excused myself and ran to my room to get razors for both of us. As I came back to the bathroom I could hear Jessie moaning, my guess was that she discovered the massage setting on the hand held shower and was pleasing herself. I was correct. I quietly sat down on the toilet and didn’t say a word until she was finished. It’s not the first time that either of us and masturbated in front of one another in fact we had done it several times… A lot.
When Jessie had finished having an orgasm, I could see her wiping the steam off the clear glass shower door. She then was able to see me sitting there, with a big smile from ear to ear. Jessie laughed saying she was so into it she hadn’t realized I had come back into the bathroom. I just laughed, open the shower door and handed her a razor. Jessie shaved her legs, arms and then did a bikini shave as usual. She finished shaving, rinsed off and stepped out so I could get in and shower.
As I showered, Jessie dried off and then sat on the toilet and we chatted. I shaved as Jessie had done until it came to my pubic hair. Ever since I started growing pubic hair I was shaving it. I had seen my mom and other woman shaved and I thought the look was beautiful and later thought it was sexy just like some hair dos are beautiful or sexy. I don’t shave completely; just a small ‘landing strip’ is left because I like the look best. I realized Jessie had quit talking so I wiped the steam from the glass and saw she was trying to watch.
“Sorry, Abs, I’ve just never seen you shave down there and always wondered how you did it. You are always so clean shaved….”
I shut off the shower, stepped out and dried off.
“Come here.” I said, leading Jessie back to my bedroom. I grabbed a large cup from the bathroom, filled it half way, and got my razor and shaving gel. I sat on bed, setting my “tools” next to me. Grabbing the round mirror off my night stand, I set it between my legs giving me a good view of my vulva. I lathered and began to shave. Jessie sat at the end of the bed facing my wide spread legs watching me shave. When I was done I looked up at her and smiled.
“See, it’s easy.” I said.
“I don’t think I could do that. I’m afraid I would cut myself.” Jessie had a look of doubt but yet was obviously interested in the finished look.
In a joking tone I said, “I could do it for you, no big deal.”
Wide eyed and excited Jessie replied, “Would you? Would you really? I just don’t think I could. Honest, I think I’d cut myself.
I looked at her not sure what to say. I offered, but was really joking, well, maybe half joking. I asked her what she wanted, how she wanted to be shaved.
“Well, I can shave the top part, I just don’t know what I want, but I know I want my lips shaved like you just did.”
I agreed to what she wanted and explained that first we needed to figure out how she wants the top shaved. After some discussion she decided she want hers like mine, just not as small of a landing strip.
So we started shaving her. I grabbed another razor and started shaving her vulva as she did the top. I stopped after just a few strokes and helped her do her part. When we finished the landing strip, I started in on her lips. I re-applied the shaving gel. Jessie tensed up a bit and moaned a soft little but deep moan. I started shaving her. I had to pull her lips this way and that from time to time to get to all the hair. A few times my hand brushed against her clit, rubbing lighting; I could hear a moan escape her. Throughout the process she was sitting up watching me but from time to time would lay back which is when I would hear soft moans. At one point she asked me to stop which I did.
“Is everything okay, Jess?”
“Um, yes, just give me a second.”
I wasn’t sure what was wrong but I did as she asked. Then she would tell me to continue and I would. When I finished I announced that I was done and it looked so smooth. I grabbed her hand and brought it down over her vulva to feel how smooth she was. As I did, I noticed a spot that still had a little stubble. She pulled her hand back and I applied more gel to finish the spot I missed. When I finished, I rested my hand by her clit so I could pull her lips from side to side to make sure I got everything. As I did, I hear Jessie gasp; she grabbed my hand and forced it over her clit making her cum. Her legs clamped shut just missing my head but trapped my hand over her clit. I tried to move my hand out of the way but made things worse… well, better for her. The movement of my hand had her moaning louder and her body shaking.
When she finished her orgasm, I kissed the top of her thigh as a sign that everything was okay. I didn’t want her to feel guilt cuming at the touch of my hand.
Jessie sat up with a look of fear on her face. I smiled and said “It’s okay. Don’t say a word. It’s okay.”
Jessie took a deep breath and let a little smile appear. I kissed her other thigh as she relaxed her legs and I was able to pull my hand free. Jessie looked down at me and simply said, “Are you sure?”
I didn’t say a word. I just smiled, bent over and kissed her hood covered clit. Jessie let out a loud moan and said thank you. I looked up at her and reminded her we still had to make dinner for everyone and that Jon and my mom would be back soon.
Jon and Mom got back as we were setting the table. Jon headed straight for the stairs to go up for a quick shower before dinner. Mom said she was going to do the same but came over to Jessie, but an arm around her shoulders and said, “Very nice. Did Abs do that?”
Jessie blushed slightly and answered, “Yes, she helped with part of it.”
Mom smiled and then headed down the hall to the shower. After dinner as we cleaned up, Jon came into the kitchen. He looked at me and then at Jessie. I noticed he was slightly red in the face.
“Hey Jessie, umm, well, hey, it looks nice. It’s pretty.” And then he walked upstairs to his room.
Jessie looked at me as if to ask what that was all about but I didn’t know. I shrugged my shoulders and we finished the dishes. I suddenly realized what Jon trying to say to Jessie.
“Jessie, Jon noticed your new look.” I said.
She looked at me with a quizzical look on her face. “What new look?”
I just looked at her, eyebrows raised and nodded towards her new landing strip. I have to admit it did look very sexy on her, but then again I have always loved the look of shaved pubic hair. Not necessarily completely shaved, but that can look sexy too, but a well groomed pubic area is just as beautiful as a new hairdo.
Mom came in shortly after Jon had walked out of the kitchen and offered to help with the dishes. We told her we were almost done so she sat and visited with us. After a little chit chat the dishes were done and we all decided to call it an early night since it had been a long day.
Mom headed to the living room after we gave kisses goodnight and Jessie and I headed up to our room. Jessie and I stopped by Jon’s room to goodnight and Jessie thanked him for his compliment earlier in the kitchen. Both Jon and Jessie stared at each other not speaking. I grabbed Jessie’s hand and as I did, she gave a little jump, grabbed my hand tight and we jogged to my room.
We flopped on my bed still holding hands when Jessie turned to me, squeezing my hand tighter and asked, “Can we talk about what happened when you shaved me?”
“Sure, if you want but we don’t have too.” I replied.
“It seems weird that nothing was said. You said it’s okay and all but… I mean what I did. I used your hand to make me cum. I was just so caught up in it, I couldn’t help myself. I was so close and you were lightly touching me, it sent me over the edge… I just needed a little more pressure and I more touch to make me… cum…”
“Jessie, it’s okay. Honestly, normally when I shave, I check how smooth I am and then I often masturbate because of all the attention down there. It’s hard to ignore.” I said.
“But I pushed your hand down there and came. I used your hand to have an orgasm.”
“And had you asked me, I would have done it for you. You wouldn’t have had to force my hand between your legs. I guess technically you didn’t, I let you move my hand there. You didn’t force me.”
“Then you kissed me. I mean you kissed my clit.”
“I know I figured if I did something like that you would know it really was okay. That you didn’t really do anything wrong or anything to be embarrassed about.” I added.
“I know. But it felt good. I couldn’t help… I almost came again just from you kissing me.” Jessie said hesitantly.
I smiled a big smile. “I know I heard you moan when I kissed your clit.”
“I did?” Jessie’s eyes went wide in surprise. “I thought I did that to myself. I moaned before I even realized I was moaning.”
Trying to change the subject a little I asked, “So do you like the new look? And how smooth you are?
Jessie smiled as she lowered her hand across her pubic area and down between her legs across her lips. “Yes, I love the new look and how smooth I am. Are you just as smooth?”
“Yes.” I replied. I grabbed Jessie’s wrist, pushed her hand down, letting her feel how smooth I was.
“Oh… You didn’t have to… Wow, you are just as smooth. Hmmm, it feels so good. I mean…” Jessie’s words trailed off as she sat up, slide down the bed and bent over me. I watched as she intently stared between my legs, bending over closer, still closer and then kissed top of the “V” between my legs.
I moaned. Instinctively, naturally, and quietly I sucked in a breath and then exhaled slowly ending in a moan. Jessie sat up, slid back so we were facing one another and smiled.
“Now you know what I felt.” She said.
I returned the smile as I slowly raised my hand, resting it on her cheek and leaned closer to her. Our eyes locked, both now leaning towards each other, our lips met, eyes closed and arms wrapping around each other. This was our first passionate kiss.
I held her face, my hands, one on each cheek. I kissed her tenderly, lovingly, with a strong hint of passion. I proceeded kissing down her neck slowly, then downward to her chest; kissing a straight line down the center between her breasts stopping even with her nipples. I looked up hoping to see approval or at least a hint to continue. I felt her hands sliding up over her abdomen, upward cupping her breasts, squeezing each one as her fingers slid to her nipples; she pinched and pulled at each nipple.
I leaned over and flicked the tip of her nipples with my tongue, first one and then the other, as I did Jessie moaned. It was a soft, quiet, deep moan from deep within her chest. I can feel her legs spread apart; a slow unintentional relaxed motion allowing the heat from between her legs to escape like a hot breath blowing against my stomach.
I took as much of her breast into my mouth, sucking hard as I slowly pulled my head up causing her breast to slowly leave my mouth, yet still hold the nipple captive. I folded my lips inward to cover my teeth then clamped down hard on her nipple. I feverishly attacked her nipple with my tongue producing long deep intense moans from Jessie. I continued the attention to her breasts, first one and then the other; back and forth I went until Jessie’s legs spread further allowing my thigh to slip between her legs. I felt the moisture from Jessie running down my thigh to the bed.
I released Jessie’s nipple as I looked up to her flushed face. I could see the wanting, lustful gleam in her eyes as she whispered, “Don’t stop Abs. Please don’t stop”. I had no intention of stopping. I didn’t need to hear her words; the look in her eyes and on her face told me all I needed to know.
I leaned up, kissed Jessie softly on her lips and then began descending, licking my way down between her breasts and over her abdomen. When I reached her newly shaved pubic area, I kissed along her neatly trimmed hair line following the small “V” shape to the point stopping for a moment to lightly lick (tease) her clit. I began to kiss and rub her hips and thighs; massaging her with controlled passion. I gently pushed Jessie’s legs further apart exposing all of her to me. I could see the moisture beading around her lips as her wetness dribbled out of her.
With very little self control, I moved my head between her legs sucking in her clit and flicking it as I had done to her nipples. I moved my hand between my legs to find I was soaking wet. I slid first one and then a second finger inside me. My thumb instinctively went to my clit and started to rub. It didn’t take long and I was ready to cum.
Jessie’s back arched forcing her hips tightly against my face as I pushed her clit to the roof of my mouth rubbing her clit with my tongue. She moaned as she placed her hands on the back of my head holding me in place. Her thighs started to quiver, her body shaking, breathing rapidly and I could feel a slight throbbing in her clit. Suddenly her hands applied more pressure on the back of my head, her legs drew tightly together and her hips started to buck up and down against my face.
I stopped rubbing her clit but kept it pinched between the roof of my mouth and my tongue as I gently tugged on it. Through gritted teeth I heard her whisper a moan over and over, “I’m cuming! I’m cuming! Abs… I’m cuming again… I can’t stop… Cuming again…”
After what seemed like hours, Jessie’s body started to relax. Her breathing uncontrollable, her legs now opened for me to move leaving her thighs still quivering I moved up the bed to face her. Jessie finally opened her eyes, raised a hand and placed it on my cheek. She kissed my forehead and then kissed my lips releasing a soft moan as she tasted her juices from my face.
“Abs, that was incredible. I’ve wanted to do that for so long now. I want to do the same to you. I want to… Do that to you. But I don’t… My legs are like pudding, I can hardly breathe. I came so hard and so many times, I can hardly move. Holy crap! That’s the first time I’ve cum like that. I had… One after the other… I didn’t think I would stop. Really, I’ve always wanted to do that to you.”
“It’s okay. We have time. Rest up.” I whispered.
“But you didn’t cum. I need…” her voice trailed off as I interrupted her.
“Oh, but I did cum, Jess. I did cum.” I assured her as I gave her a devilish grin.
“You did? Oh you….” She didn’t finish what she was going to say, only smiled and laid her head on my chest.
Jessie moved closer, one leg now draped over me, an arm lay across my stomach and her head resting on my chest. It wasn’t long and we were sleeping, still cuddling, and clinging to one another.