I want to preface this by saying, I love my girlfriend. I really do. I’ve probably loved Emily since the first time we met. It’s just that, honestly, she is just so damn shy and reserved! For the two years we’d been together, we had hardly done a thing!
Ok, so for a year and a half of that, she was ‘under age’ as she likes to put it. We met in highschool, when I was a senior, and she was a grade behind me. But now we were both fully fledged adults, and honestly I was getting a little tired of her excuses. I felt like everyone was out there having tons of fun but her and me!
I guess it goes back to that adage of every guy wanting his girl to be a slut, but only a slut for him, and him alone. Her reserved nature was what had initially attracted me to her in the first place. It was just so damn frustrating now! Did you know I hadn’t even seen her in a swimsuit!? She’s that damn shy!
But, I still love her. We have so much in common, and get along so well. I guess I can wait for her, for when she is ready. I know she is worth the wait. And it’s not like we haven’t done anything together. She’s allowed me to feel her up, even underneath her clothes. She’s jerked me off a few times, although it’s always been underneath a blanket, so she hasn’t seen me either. It’s just none of this has been in the fashion I would have preferred.
She has a thing about nudity, I guess. Maybe a phobia? Every time we’ve been making out, and I’ve tried to even just pull her top up a little, she’ll always do this thing where she slaps my hand away. It’s always kind of playful, and not really in a mean way. She just giggles and blushes at me, and says, “Erick, I’m not ready…” So I do my best to respect her boundaries.
Friday night had become our night together, whether it was as a date night, or just hanging out at one of our houses. This night was no exception. We met up at her house, since her parents were going to be gone for the night, and put on a movie and ordered some food. It didn’t take long for us to stop paying attention to the movie. One thing Emily absolutely loved was making out. We were going at it like fiends before the first act of the film had even ended!
I had a really good feeling about tonight. Emily had made a big deal to me about her parents being gone, and how she was very much looking forward to our time together. She had even implied that maybe I should spend the night at her place too. So you can’t blame me for at least trying one more time.
Again I got, “Erick, I’m not ready…” I’ll admit it was frustrating. I had just spent the last number of minutes with one of my hands up her shirt, even underneath her bra for a bit! I had felt her nipple go hard, and heard all of her purrs and sighs as I massaged her. Why was she being so infuriating!
I tried to be patient though, while still letting her know of my disappointment. “Emily, honey, what’s the matter? Why is it any time I try to take anything off of you, you always stop me? Is it me?”
“What? No, Erick, sweetie, it’s not you. You’re so handsome and honestly, really sexy.” She said, giving me a cute blushing smile that I loved so much.
“Well, then, what is it? Are you super religious, and you want to wait until you are married?”
“No, you know I don’t believe in that stuff, really…”
“Is it that you have some kind of scar or something you’re afraid to show me? Because, honestly, honey, that’s not going to change the way I feel about you. You know I would love you no matter what.”
She really smiled big at that one. “No, I don’t have any scars, or anything like that.”
“Well, then what is it?”
“It’s…” She looked away from me for a moment, I think trying to build up her courage to tell me. “I’ve just never been naked in front of anyone before.” She looked back at me. “I mean, when I was still young, sure, but by the time I was potty trained I was taking care of myself for the most part.”
“So you’re self-conscious about your body?” I asked.
“No. It’s not that. I honestly really like my body, and how it looks. I just can’t stand the thought of anyone else seeing it…” She explained.
I wish I could tell you something else happened that night, but it didn’t. We just snuggled together underneath one of her blankets and watched the rest of the movie.
One thing I love about Emily is just how ticklish her little body is. Her cute tummy, especially on the sides, was my favorite part of her to tickle. But sometimes she would also leave her dainty feet bare, and I would relentlessly tickle her soles. It just so happened to be a few weeks later, that we were having a bit of tickling fun in her bedroom after a long day at school.
“No! Erick! Please!” She was squealing and squirming, trying to get away from me. I was a lot bigger and stronger than she was, so it was pretty easy for me to keep her pinned in place on her bed while I had my fun with her. I always loved to take her past that point where she was begging me to stop. She was still giggling uncontrollably as she begged, “Please, I’ll do anything to make you stop! Please, Erick!”
I couldn’t refuse an offer like that, so slowed my dancing fingers to a crawl, and then a stop, but left them in place under her sweater so she would know I could start up again with the tickling any time I wanted. “How ‘bout you take off your top?” I grinned at her. I was honestly expecting nothing, but I figured it was worth a shot.
“Erick!” Her face turned beet red. Then I saw her get a determined look in her eyes. “Fine, I’ll agree to take off my sweater, if you can make me laugh within 30 seconds. If not, I get to take off your pants.” She smiled up at me, challenging me to accept her offer.
How can I refuse an offer like that? “It’s a deal, but I get to tickle you anywhere I want.”
“Anywhere you can reach.” She countered, and I agreed with a nod. She leaned over, and set a timer on her phone, leaving it on the nightstand next to her bed. Then she looked back at me with a smirk, and said, “Go!”
I was immediately digging into her sides with a fury I had never used before. Her little body was squirming and writhing around like her life depended on it, but she was determined not to crack! I did everything I could to get to her, but she was resolute. 30 seconds turned out to not be a long time, and I was disappointed when her phone began making that beeping noise! I could hear her let out a deep sigh of relief after I stopped my manipulation on her tummy.
“Come on! Get up!” She said, giving me a satisfied smirk. I could see she wanted to revel in this.
I had lost fair and square though, so I didn’t give her much of a fight. “I know. I know. I have to take my pants off…” I said, getting up from her bed.
She sat up, swinging her legs off the side, shaking her head. “Nope! You don’t get to take them off. I do!” She reached over and popped the top button of my jeans.
“Emily!” I laughed. She’d never been this forceful before, and it was really surprising to me. I grabbed her hands though, before she could get to unzipping my fly. “I’ll let you do it, only if you agree to continue playing.” I offered.
“Huh?” She looked up at me with her questioning eyes.
“It’ll be your turn to tickle me next. If I laugh you get to take something else off of me. If I don’t, I get to take whatever I want off of you.” I smirked down at her, enjoying the contemplating look she was giving me. “We’ll play until one of us is naked. But if you laugh while being tickled you lose your turn.” I explained.
“Ohhh…! I hardly ever get to tickle you! You’re on!” She stuck her hand out like she wanted me to shake it, but when I took my hand off of her other one, she used the opportunity to slip my jeans down to my knees, giggling uncontrollably.
I was honestly a bit embarrassed to have been caught out like that by her, but I knew soon I would be getting my revenge on her. I slipped my jeans the rest of the way off, letting her laughter be a distraction so she wouldn’t see me do it. By the time she was done giggling, I was just standing there in my t-shirt and boxers, and my socks down below.
She eyed me up and down, and then patted the bed a few times with her hands, inviting me to come sit. “I get to tickle you anywhere I can reach, remember.” She said to me, with just the wickedest of grins.
Maybe I was a little too cocky, but she had yet to get me to crack anytime she had tickled me in the past. I knew I had this in the bag. She set up a new timer, and then she was on top of me in a flash. Her soft fingers immediately went to my thighs. Obviously she was going to try and use the fact that I had lost my pants against me. I just shrugged at her and shook my head. She frowned at me, getting frustrated, but I knew she wouldn’t give up that easily. She reached in between my legs, trying the insides of my thighs next, and while it felt highly enjoyable, it wasn’t going to make me laugh. I just smirked at her effort.
She tried the backs of my calves next, but that got her nowhere. She tried the bottom of my feet, and I was ever so thankful I was wearing socks. I knew for a fact I would have lost in an instant if I hadn’t still been wearing them. I checked the time left on her phone, and there were just over 10 seconds left. Then she found my only exposed weakness. The back of my knees! She knew she had hit on something, since my eyes had opened a little wider. It took everything inside of me not to make any noise, and I clutched the edge of her mattress as tightly as I could, determined not to lose it.
I had just made it! The timer went off, and then I cracked. “No, Emily, it’s over!” I giggled, grabbing her wrists to get her sweet little fingers away from me. “Ok, now I get to take something off of you.” I was back to smirking, enjoying the way she was blushing at me.
She held her arms above her head. I guess she expected me to take off her sweater since that is what I had said I would take off to begin with. She was sorely mistaken though, I was way smarter than that. “Nope, not your sweater.”
“What? That’s what you said you were going to take.” She looked at me in confusion.
“No, I said I get to take anything of yours off that I want.” I corrected her. “Give me your leg.” She was still looking at me with that confused little brow of hers, as I pulled her pant leg up just a bit. Then it dawned on her what I was doing, as I slowly slipped her sock down her ankle, and off of her foot and her charming little toes. I could see the worry written all over her face. “Do we count socks separately, or together?” I asked. Now I was the one reveling in her embarrassment.
“You only get to take one thing!” She complained to me. We both knew it wouldn’t matter anyway. I had just exposed her biggest weakness. The soles of her feet were the most sensitive part of her body for tickling, she had admitted that fact to me all on her own. She knew she had lost, it was just a matter of formality now.
“Set the timer then.” I said, cool as a cucumber. Her apprehension was palpable as she turned to do just that. I let her lie down on the bed and get comfortable, saying, “Just relax, honey. You and I both know there’s no rush. You’ve already lost.” I knew I was being brash, but I couldn’t help taking pleasure in her unease. I toyed with her a little, letting the timer tick its way down, just smirking at her. At the 15 second mark, I reached over, and just lightly ran my fingernail over her arch. Immediately she squealed with laughter! “Your other foot, please.” I held my hand out expectantly, and stripped her of her other sock.
“Don’t I get a turn now?” She looked at me wistfully, holding out hope for a chance she could still win.
“Nope. You laughed. That means it’s my turn again.” I explained, and she just pouted.
Another timer set, and another squeal from my girlfriend when I flicked my fingers over her sole! There was nothing she could do now. The game was already lost for her. I had her sit up, so that I could remove her sweater, finally getting the prize I had tried to get from her at the beginning. This game, though, was going to give me the ultimate prize!
“Do you think you even need to set the timer?” I asked, checking her out. She still had a shirt on, a spaghetti strapped shirt I had never seen her in before. In fact, this might have been the first time I had seen any bit of cleavage from her. I’ll tell you, she looked fricken cute already, and there were still so many things to take off of her!
“Maybe you can be fair to me, and let me have another turn at you?” She requested, but I wasn’t going to let her get the chance. She should have listened to the rules of the game a little better if she wanted something different. “Can I at least set the timer a little lower? 20 seconds?” She pleaded.
Not that it would do her any bit of good, but I relented. I guess I still had a heart for her. “Ok, 20 seconds, but that’s the only thing you’re getting… Well, you’re getting naked too!” I teased, and her face turned that deep shade of red once again.
Even with 20 seconds, she still couldn’t hold her laughter in. This time she tried. She really did. I could see her cheeks puffing up, and her face turning almost purple. I think she was trying to hold her breath in, in order to try not to laugh. But her feet were just too damn ticklish for her! And I had both to target now. She burst out laughing at the 12 second mark.
I now had the privilege of removing another piece of clothing from her cute little body. I guess I was starting to feel a little frisky, since I went for the top button of her jeans. She looked up at me from the bed with wide eyed wonder as I straddled her, and slowly slid the jeans down her smooth, and soon to be very bare, legs.
It was time for more tickling! Another few seconds, and another part of her outfit lost. I knew I could have gone right to the good stuff now. It was my choice what to remove from her, but I wanted to draw this out. I wanted her to feel the excitement I was feeling, like I was slowly unwrapping a present at Christmas time.
I’m sure I gave her the most elated look as I did away with her shirt. Now all she had left were her matching set of undies. A light pink bra, with a floral pattern sewn into it, and the panties that went with it. I swear I could almost make out the shape of her privates now, as the underwear hugged quite tightly to her body.
She blushed up at me, and then her eyes seemed to almost bug out of their sockets. “Erick! Your…! Your…!” She didn’t say it, and just pointed.
I guess I was getting pretty turned on. I looked down at myself, only to find my cock peeking out of the hole in my boxers! I had just unintentionally flashed my girlfriend with my most private bit!
The smirk she got on her lips gave me some relief though. And I couldn’t help feeling a little proud. She was the one meant to be naked, though, not me, so I quickly fixed myself.
“Only two items left, and then you’ll be totally, fully, completely, bare, butt spankin’ NAKED!” I taunted her, making her face turn that rosy red hue I was learning I love so much! “Tell you what, I’ll drop the timer down to 10 seconds if you agree to stay naked and do whatever I say for 10 full minutes when I win.”
I could see the gears turning in her head. She had been able to last a full 12 seconds by holding her breath, and I’m sure she thought she could do it again. This would give her a real fighting chance, at least I hoped that’s what she was thinking. “Ok, but only if you agree to stay naked for 60 minutes, or one full hour, if I can last the whole time.” She countered.
“Sudden death huh? Alright, but then I win both your bra, and your panties.” I decided if she was going to up the ante, so was I. She nodded her agreement, getting that determined look in her eyes again.
Setting the timer on her phone, it came down to this. Me naked for a full hour, or her naked and at my mercy for 10 minutes.
The timer started, and instantly I attacked. Maybe it was a cheap move, but I don’t care. Her arms were still above her head to reach for her phone, so I used that to my advantage. My hands squirmed deep into the pits of her arms, and I could see the surprised look on her face as the sensation rocked her whole little body. She couldn’t move away from me now though, even if she had tried. I had to lay on top of her to reach her in this position.
Suddenly, all the air burst from her lungs! And a delightful giggling sound emanated from deep within her throat! I had won! There was no question. 3… 2… 1… and the timer went off.
I could see her staring up at me with her baby blue eyes, realizing she knew what it meant that she had lost. I couldn’t help grinning down at her. I was still sort of hovering above her, resting on my elbows, as she lay beneath me. We stared into each other’s eyes for what felt like forever, and then our lips finally met.
I had won, and I was going to make sure she lived up to every part of the bargain. As much as I loved kissing her, I think I could wait until later. I got up from the bed, probably giving her the biggest smile of my life. “Alright, Emily, time to pay up.” She looked up at me with those big blue eyes, and I could see the nervousness inside of her as she accepted my hand to get to her feet as well.
Her long, light brown hair had been up in a bun before all the tickling and kissing had knocked her hair tie loose, but now it messily came down over one of her shoulders. “No, don’t put it back up.” I told her, as she attempted to fix it. “I like it better this way.”
I went to stand behind her, looking her body up and down in her tight, sexy little underwear. I’m not exactly sure, but I think the style of undies she was wearing was called bikini cut. I do know it left part of her cheeks showing in the back. I couldn’t wait to see what her cute little butt would look like bare!
The first thing that needed to go was her bra. This was going to be a first for me, as I had never had the chance to undo one before. At least I had the advantage of seeing it, since I had gone behind her. I had it figured out quickly though, just pull it together, and let the clasps go. Now it was just hanging from her shoulders loosely.
I came back around to her front, and she quickly made sure her arms kept the garment in place. I had dreamt and desired to see that perky little pair of hers for so long, and I wanted to be in the exact right position for the big reveal! I couldn’t totally read her anymore. There was a coy shyness for sure, but I think I also saw a bit of a smile at the corner of her eyes. One thing was for sure, I had never seen her face more red in my life! And that should tell you something, since this girl was always blushing at me.
I reached my hands towards her, taking a strap from her shoulders in each. “You ready?” I asked her.
I could see her contemplating, and then she nodded her head. Very lightly, and as tenderly as I could, I pulled her bra away from her body. I only noticed her looking down at the floor in shame for a second. I was much too focused on checking out her chest to pay much attention to that for long. Oh my GOD! She had perfect tits! No droop or sag, no blemish on her skin, just the cutest little pink nipples that seemed to want to point themselves right at me! WOW!
And I wasn’t even done. There were still her panties to take off! Maybe it was cheating, but I waited. She was only supposed to spend 10 minutes naked in front of me, but she couldn’t start the timer until her panties were off too. I wasn’t going to complain about any extra time with her like this, and decided to wait for her to make the next move.
Eventually she looked back up at me. I could see it in her eyes then. Relief. The same feeling I had gotten earlier when she saw me poking out. I must have been giving her a genuinely appreciative smile. “Erick…?” She asked me. Her face was still blushing, but at least it wasn’t as red as before.
I knew exactly what she was asking for. “You want me to take off your panties?”
I could see her getting flustered at the question. Neither yes or no were a good option for her to answer me with. She just went with a simple head nod. That was all the confirmation I needed, so I got down to my knees in front of her. I then reached my arms up, and hooked my fingers into her waistband. She grabbed her bare boobs in her hands to try and gain back some of the modesty she had lost, and got this deer in the headlights look on her face.
“You ready?” I asked again.
“I… I…” She mumbled some. “Yes!” She finally squeaked. I didn’t want to completely tourture her, so I did this one pretty fast. With her standing with her feet a couple inches apart, her panties slid down her legs freely. I didn’t watch her pink underwear come down though. No, my eyes were locked on to the no longer hidden treasure nestled between her legs.
MY GOD! She was almost smooth down there. Just a light dusting of almost blonde looking hair above what I can only describe as perfect peach looking lips! I was already in love with this girl, but if I hadn’t been, I would be now! I guess I could maybe describe the feeling as falling into lust.
I stood up, and took a step back, so that I could take her all in. Damn she was stunning! Fit and athletic, but not overly so, and super feminine. I guess she couldn’t stand me looking her over, since she moved her one arm to cover up her nipples as well as she could, and used her other hand to cover that sweet fruit between her legs.
“10 minutes. Remember?” I said, reaching for her phone.
“I know, Erick…” She got a different sort of determined look in her eye. It was almost like she wanted to prove to me and to herself that she could do it.
I hit the timer, and then immediately took charge of her. “I want you to move your arms out of the way. In fact, put them on top of your head, that way you’re not tempted to cover up again.”
She acquessed to my demand, knowing she had to. I was fully within my right to tell her to do this per the agreement of the bet. “Good. Now slowly turn around.” I told her. Finally I got to see her cute little bare ass! “No, don’t stop. Just keep spinning, but very slowly. Like you want to make sure I can see every inch of your bare body.” I explained. I only wish I could have seen the expression on her face just then, but alas, she was facing away from me at the time.
I knew I had a limited amount of time, so I only let her spin like that a few times. But now she was fully aware I had seen every inch of her naked body. Now it was time for some more fun stuff. “Em, you still have the jump rope you use when you work out in your room, right?”
“Oh come on!” For the first time she made a complaint to me.
“You know there’s so many more embarrassing things I could make you do while naked. I think doing a bit of naked jump roping is pretty tame, honestly.” I explained.
Her face softened, and I could see she was in agreement with me. “Ok. I’ll do it.” She went over to grab the rope, holding it between both hands. “I guess this isn’t so terrible.” She said as she began to jump. She was still trying to be modest though, as she had turned her back to me. I could see her butt jiggling with each bounce she made, but what I really wanted to see was her little chest globes bouncing.
“Turn around Emily.” I think my voice sounded like I was scolding her when I said this, and maybe that is why she was so quick to comply. Oh my LORD! This was even better than I had imagined! Bounce! Bounce! Bounce! Went her boobs, and boy was I mesmerized.
I realized the timer was still ticking down, and I had a few things I still wanted her to do before my time was up. “Enough jumping, Em. You look like you could use a breather. Why don’t you lie down on the bed and catch your breath.” She seemed happy to comply with this one. I don’t think she realized what I was about to have her do.
“Good, Em. Now just pull your knees up. Yeah, that’s it, like you were gonna do a sit-up. Now grab the back of your knees with your hands, and pull your legs wide open for me.” That was absolutely the most shocked look I had ever seen her give to me, but I think any bit of fight she had left inside of her had gone. Ever so cautiously and slowly, she completed my request.
That little peach between her legs split open, and now I could see everything in between! It was the cutest shade of bubblegum pink in the world! The thing that surprised me most, was that everything in between seemed to be totally soaked! She was totally turned on by this!
Her little pearl at the top there stood out quite a bit too! There was no way she could deny the truth. “You’re enjoying yourself!” I gave her probably the largest smirk in the world.
“Um… Uh…” She couldn’t deny it, but I guess it was difficult for her to admit it as well.
“Em, can I ask you something?”
“I… I guess…” She seemed a bit petrified, still holding herself open for me.
“Have you ever wondered what it would be like if I went down on you?”
“Oh my god!” She pursed her lips, looking at me with her still wide baby blue eyes. “Would you…? Would you really want to do that?” She seems to be astonished at me, like in a million years she would never expect I would bring this up.
I nodded my head to her. “I’ve always dreamt about doing this. Doing this to you. You’ve just never given me the chance.” I don’t know if I had exactly gotten her approval, but I certainly didn’t get any resistance from her as I got onto the bed in between her legs.
I was just about to have my first taste of her sweet peach, when that damn timer went off! “Damnit!” I complained.
“Forget the timer!” She said boldly. “You can do whatever you want with me Erick…”
She certainly lived up to every part of the bargain, and then some! Only she ended up winning in the end too, because I also ended up getting naked for her, and it was way longer than just 60 minutes… And that is the story of our first time together.