Feels Like the First Time – 2
Brent and Chelsea celebrate her birthday in the city
“Get back to me tomorrow Brent. Let me think. The city is going to cost you. Plus dinner? Must be a special occasion.”
“Well yeah. Girlfriend’s birthday. I want it to be a nice night.”
“Enough said. Treat her right.”
The next day Frank asked me to come up to his office. “Good luck Brent. We book blocks of rooms at hotels for visiting management from out of town. Seems there’s an open one not being used next Friday. It’s yours. Take the money you would have spent on a room and add it to your dinner budget and go here. It’s Italian. Very good.” He gave me a piece of paper with the restaurant name and address.
“Thanks a lot. She’ll be impressed.”
“Just make sure she’s more impressed by you. Dress nice. Treat her special. I can let you use a pool car. Be careful. And take a half day Friday. Don’t have her taking the bus in.”
“Really, thanks. I owe you one.”
“You’re a smart kid. Too bad you didn’t finish college, but you keep working hard and you’ll move up.”
Now I was set. Way better than I thought I could do. No way would I take Chelsea to a cheap dump, but this even beat Holiday Inn. I called Chelsea to make plans; told her we’d be dressing up, but how could we arrange for me to pick her up?
“No worries. I told my parents I was spending the night with you.”
“What? They’ll, well I don’t know what they’ll do when they see me.”
“I told them I’m 18. I also told my mother it’s not like I hadn’t done it before. We are going to do it, right?”
“What did she say? And yes, I was hoping you’d want to.”
“You’re so funny. I’ve been ready to have sex with you for weeks now. She seemed surprised, again mentioned protection. I told her I’d started on the pill three months ago. Dad says, ‘Yes but you can still catch something.’ I hope you don’t mind but I said you were as clean as possible, like brand new.”
“So your parents know I’m a virgin.”
“Yeah, sorry, but I think that earned you points.”
I think I earned a few more when I drove up in a Town Car wearing a suit. Feeling just a little uncomfortable facing the family I knocked on the door. Chelsea’s sister answered and as I walked in she whispered, “Somebody’s getting laid tonight.” My face must have reddened. Her parents greeted me, looked me over. Her father took me aside.
“Be sure of what you’re doing, you better not break her heart.”
“No, I like Chelsea a lot. I’m not, you know, um, using her or something.”
“Treat my girl with respect. I know she’s not a kid anymore but she’ll always be my little girl.”
“I will, I promise.”
Chelsea looked amazing. Her dress showed off her figure to perfection. The shorter dress got a look from her mother, but it wasn’t too short. And it showed off her nice legs. The drive into the city wasn’t too bad as we were before rush hour. I found a parking spot on the east side and we walked around the neighborhoods, then down to 5th avenue, blending in with the crowds. I longed for my first time, but I was determined to make this about more than that. We held hands, looked in shop windows, then made our way up to the address Frank had given me. I gave my name and we were led immediately to a romantic table in a corner. Candle light, real linens, sparkling silverware. The meal was as good as I was told it would be. I needed every bit of what I’d saved on the hotel. Chelsea was duly impressed with my choices. Walking along the park she said, “That really was very good. So classy.” She held me around the arm, leaning her head on me as she walked.
“It’s nice to go out with an adult”, she added.
“I’m barely an adult. And I can act the fool with the best of them.”
“I know, but you have a real job, you can order properly from a menu at a fancy place. You even KNOW a fancy place. I’m kind of looking forward to the rest of the night.”
“Almost there.” When we got to the hotel the doorman let us in. I’d checked in earlier to avoid any awkwardness now. We’d stopped to get Chelsea’s overnight bag on the way over.
“Oh my god, this place is sooo nice. How could you afford this?”
“I know people. Connections at work.”
“See grown up stuff.”
We took the elevator to the 12th floor. As promised the room had a spectacular view of the park. “Oh what a view. Let’s leave the curtains wide open.” We did. There was a bottle of champagne on ice. Compliments of Frank. I opened and poured. Then stood looking at Chelsea.
“A man feeds me like that, takes me to a beautiful hotel with an amazing view. Plus he’s smart and fun and cute. Yeah, I’m ready.”
I brought her to me. We kissed. I hugged her. We kissed some more, looked at the view. “Chels, can I undress you.”
“Oh, yes. MMm, definitely.”
I was getting more nervous by the minute. I found the clasp, then the zipper on the back of her dress. So far so good. She caressed my face, kissed me, whispered words of encouragement. I slipped the dress off her shoulders, let it fall, she stepped out of it and I tossed it on the sofa. I hugged her, feeling the warmth of her body, then got to work on the bra.
“The hook is in front.”
“Oh ok thanks.” Now my fumbling fingers were in between her sexy mounds and yes finally, an easy enough hook. And wow, there they were. I took one in each hand to hold, lift, touch, squeeze, run my thumbs on her nipples. Amazing. But I had more work to do. I knelt before her, looked up into her eyes, she placed her hands on my shoulders. Smiled. I hooked my thumbs into her panties and slid then down. She kicked them aside. I was staring up at Chelsea, now I looked straight ahead. She’d trimmed her bush, still a tuft of hair above, clean on the sides, I reached, touched, ran my hand from top to bottom.
“Do you like it? It took me ages to get it all.” I looked up again, my hand continuing to explore.
“Oh stop, it’s just my pussy cleaned up a bit for my man. You have time to explore later, now come up here.” I stood, we kissed, mmm, how we kissed. I was now holding my first nude woman. My hand slid down her back, cupped her ass, I kept it there.”Now my turn. Hands off so I can do this.” Chelsea removed my tie, unbuttoned my shirt, then used her hands to feel my chest, around the sides, my abs. “Nice bod you have here. Can’t wait to have some time with it.” She slid my shirt off, then lowered herself to her knees. Oh fuck what a sight. Naked, on her knees, opening my belt. I felt ready to burst. Hold on Brent, hold on. Deep breath. Chelsea opened the button, slid down the zipper, I kicked off my shoes, she slid my pants down. The tent in my boxers obvious. I stepped out of my pants, she tossed them aside, her hands moved from the sides of my boxers, around back, feeling the tension in my muscles, then around front, testing the outline of my cock, she pulled down on my shorts, my cock sprang free, the boxers gone, my cock pointed out towards Chelsea. She grasped it, held it gently. Continued holding it as she stood, letting her hand slide off.
“Are you ready, Brent?”
We moved to the bed, “Lie down. It’ll be easier. Take it easy lover. Try to relax.”
“I’m trying, but I might, you know.” She kissed me. Wriggled her nose on mine.
“That’s the best part. We can just do it again. Because someone was thoughtful enough to book a whole night.”
I wanted to close my eyes and enjoy the feeling, but I wanted to watch Chelsea. She was straddling me, sitting on me, her sweet breasts sitting high on her chest. Her tuft of hair resting on mine.
“OK here we go.” She lifted her hips, reached under with her hand. I could feel her holding me, moving me, aiming, then I’m touching wetness. She leaned back a little, the head is just in, then more, more, she’s so tight. But soft, warm, wet. Her eyes are closed, concentrating, adjusting to me, back more, then she’s sitting on me again. “Ah, perfect fit. You feel so nice inside me. How are you?”
“It feels better than I could have imagined. Way, way better. I can’t believe it, finally. Thanks.”
“Oh the pleasure is mine too. Now let’s do some more.” She rocked forward, I could feel how her body held me as she slid off, then rocked back and on. Chelsea rocked back and forth a few more times.”
“Oh oh Chels I can’t hold it. Sorry can…”
“Just let go, let me feel you. This will be my first.”
“Oh, uh.” I came, the best orgasm I’d had, her muscles milking me, feeling my semen shooting into that warm embrace.
“Oh yeah, nice, I can feel it. Warm, coating me inside. Oh that’s nice, I like it.”
Finished soon after we started, Chelsea lay down on me. I felt it seeping out of her onto me. “Thanks Chels. Thanks.”
“Happy to be your first. It would have been nice anywhere but to treat me like this for my birthday, I’ll always remember.”
We stayed that way in the after glow just lightly kissing and touching. I so wanted to explore her body, now unrushed, unclothed, available for sharing. But I also wanted to savor the moment. It was still early.
“Chels, why did you say, this will be my first? None of my business really, but I thought you did already.”
“I did. A few times with a couple of teen guys. I kind of wish you were my first, but then you’d have had to deal with all the ‘ouch it hurts stuff’, but yeah, you’re the first, only person who has cum inside me, uncovered like that. That makes me happy. I had something to give you.”
“Thanks, but don’t feel bad. You just gave me the best time ever.”
“Oh silly, it’s the best because it’s the first and only at the moment. It’s only going to get better as we figure this out. I really haven’t done it much myself.” She reached down between us. “Seems you’re ready to try again. Your choice.”
“I think I’d like to be on top so I can do the work.”
“Ok but not too hard at first. I’m getting used to you, and myself.” I positioned myself over Chelsea. She made way with her legs and guided me into her. Holding myself up I tentatively pushed in, concerned that I might go too hard. “It’s ok, you won’t hurt me. Just push in and out, slow at first.” I pushed all the way in, that felt great, and pulled most of the way out, that felt pretty good too. I leaned down and kissed her, easier at first, then with more passion as I rocked in and out of her. I’d found a rhythm where I could both make out and keep my cock busy.
“Oh, this is nice Brent. MMM, so. Oh so intimate. That’s it, rock your hips up into me. Oh you’re hitting me just right.”
I put my head alongside hers and concentrated on keeping my hips moving like I was. If she liked it I wanted to keep doing it. Chelsea locked her legs behind my back and let me keep fucking her that way. We were building up a sweat, but I had energy and now stamina. Chelsea said, “Let’s switch up. You’re strong. Sit back on your legs. Now pull me to you, hold me up by the ass or hips. OK now lift up, let me get you in. Good, there you go, hold me and go to town.” Now on my knees, not holding myself up I could drive myself into her with each thrust. I could also watch her boobs lift and bounce, and see her face, eyes closed, mouth open, slight “uh, uh, uh” with each time we’d meet. Finally I could feel the tingling. “I’m getting close.”
“No not yet. Slow just a little. I can get there too.” Chelsea reached forward and began circling her clit, then more frantically, breathing heavily, deep breaths. “OK, now, now, go hard.” I picked up the pace and began holding her in place and rocking my hips to give her my cock. She let out a sound kind of like, “eee eee eee”. I came. She said, “Don’t stop.” I was all out but kept feeding her my semi hard cock. She gripped the bed with both hands and rode a wave. Then calmed, “uh huh. ahh”. “That was fucking awesome Brent.” Now not only had I finally gotten laid, I’d done it right. She kissed me all over my face. I mean, a lot.
“Oh wow. Pro lover type stuff there. Kick those teens to the curb, I have a real man now.” I could only smile. “Quite a work out. Could you refill our glasses?” I got up to get the bottle. “Oh look at you all confident now strolling around naked.”
“You’ve seen it all. Nothing to hide.”
“I like what I’m seeing too.” I refilled and settled in next to Chelsea. “So, lover boy, you done for the night, or might you be able to handle a night cap?”
“Don’t know. Uncharted territory. We can sure try at some point.”
“I’m going to grab a washcloth. You know I’m not shy.” Chelsea casually got up and walked to the bathroom. Having seen her in bits and pieces the past month or two, seeing her all at once was something much more. I looked forward to getting to know it all much better. “I have a suggestion, Brent. Let’s clean up our mess then let’s explore. It’s usually a big rush, but I’d like to check out your equipment and you can poke around downstairs too.” Perfect. I’ve been wanting to get down and check around. We got side by side facing each other, head to foot. Chelsea started turning my soft cock this way and that, stretching the skin. “So you’re circumcised. Haven’t seen a foreskin in person. I like how your balls sit in the palm of my hand. How hard can I squeeze them?”
“Ooh, not hard. Roll them easy. That feels good.”
“So it stays like this until needed for action?”
“No it’ll shrink up a little more, or hang a bit longer. Just depends.”
“Cool. Oh, what are you doing down there?”
“Working my way through the filing cabinet. You have all kinds of different areas here. So this is the clitoris hiding up here?”
“Hey now! Yes that’s it.”
“Fun. Press the button, watch Chelsea take off.”
“Yeah but if you start, you better finish.”
“OK, so my penis fit in there?” I put in a finger and poked around.
“Yes, stretched me just enough to feel full and wonderful.” I leaned closer, licked the length of her slit. Kissed her clit. Wiggled my finger.
“Oh, just, yeah, all that stuff.”
I licked around the different folds, nibbled on various parts, tried a second finger. Now that was tighter. Then licked on her clit, all around it, moved my fingers in and out, touching everywhere inside. Licking, sucking. She’d forgotten about my cock. Her two hands were now on my head. Her legs holding me in place. I had no choice but to feast on her pussy. She was squeezing my head, making her ‘eeeeee’ sounds, now “eeeh, eeh, eh”, then suddenly “AAAh OOOOOH” bucking her hips, pushing herself into me. Holding holding, holding, then, “uuuuuuuuuuh”.
“Oh hell. Fucking hell.”
“Wow, what did I do Chels?. Well I know what I was doing, but…”
“Oh shush come here” Instead she switched positions. Kissed me hard on the mouth. Just sucking the breath from me. “Oh fuck, so intense.”
She hugged me, rocked me, kissed me. “What a night. First class all the way. Wait til I tell the girls.”
“Wait what, you’re going to talk about this with your friends?”
“Just Jenny and Karin.”
“Listen. I promise, promise I will leave out the virgin part. But if you think I’m not going to tell them about dinner in the city, this hotel, kick ass sex and heart stopping orgasms from primo pussy eating, you don’t know girls. They will be SOOOOO jealous. Just wait until the next time they see you. They will look at you in a whole different way.”
“You won’t tell your friends you banged a hot chick?”
“No I won’t go bragging. If someone asks if we’ve done anything I guess I’d say yes. It’s private.”
“You’re sweet. But please don’t make me keep it in?”
“Ok, except not the virgin part. Deal?”
“Deal. OK one more thing before we get some rest. It’s gonna be cool sleeping naked together. MMM. But I think you’ve got one more in you. And you’ve earned it.”
“What? I mean, I’ll do it as many times as I can. But what are you thinking?”
“Special night I want to try something I’ve never done. I could never get a cock all the way in. I gag. But time to work on that.”
“You don’t HAVE to. I like your blowjobs.”
“Yeah yeah they say there’s no such thing as a bad one. But you deserve better. I may end up barfing on your crotch, but…”
“Haha ok, let me at it.”
She had me lay back, worked on the best angle to approach. Settled for being alongside me facing down. Nice view from here for me. I rested my hand on Chelsea’s ass, caressing it softly. . She licked and got plenty of saliva on my cock, held it and put half of it in. A little more. Then gag, pull up. Catching her breath. “Have to relax. Not panic. But at the back of my mouth I start closing up.” Another try, swallowing, not quite. I can still see an inch or more. She came back up for air. “Sorry. You were good, great. I want to do this.”
“Don’t hurt yourself. I’m happy with what you do.”
“It’s mind over matter. No gagging. It’ll fit.” Once more, breathing through her nose, down she goes, farther than before. She must have passed the gag spot. “Ugh, almost. You’re getting in my throat now, I just can’t finish. OK this time if I get to the same spot and give thumbs up, push my head down.”
“Yeah, thumbs up means it’s ok.” One final attempt. Chelsea’s got slobber all over my cock, her mouth wide open, and down she goes on my cock. Down, almost…thumbs up. I push. My cock disappears. I pull my hand away. She holds it there then pulls up gasping for breath. “I did it. You boy, got deepthroated. I have no idea how chicks do that so easily.”
“Wow, that looked awesome. Felt good too. But don’t be killing yourself. Feel free to just take on the top part whenever you’re in the mood.”
“No sense wasting this.” Chelsea hopped on and bounced up and down on my cock. Changing her angles, leaning forward, leaning back. “OOh I have an idea.” She got up and ran to the open window. Propped her hands on the window and called me. “Come on, let’s do it while looking at the park. Maybe out there someone with binoculars will watch us.” I got up behind Chelsea and positioned myself so I could push my cock up into her. Holding her hips I was able to drive up, pumping my cock in and out.
“Oh, nothing better. A hard cock inside me and an amazing view. Oh go harder.” I cupped her breasts, played with her nipples, reached around and teased her clit. Then I tensed and shot a much smaller load into her. I hugged her and looked at the view. Scooping Chelsea up I carried her back to the bed where we landed, bounced, laughed, tickling and kissing. Then exhausted we decided to call it a night.
We showered then slept, enjoying the feel of our partners’ body.
When you’ve never done it before, waking up and realizing that yes, you are indeed lying naked with a hot young woman, is the most invigorating feeling in the world. When that hot young woman is caressing your balls and running her hand along your hard cock, it goes to another level.
“MMM”, was all I needed to say.
“You’re awake, you’ve been UP for a little while already. Are they always hard like this in the morning? This is my first overnight with a guy.”
“I guess, a lot of mornings, but having you next to me sure helped.”
Chelsea put her arms around me, hugged, kissed me in various places. Ran her fingernails down my chest, around to my back, down to my ass cheeks.
“Brent, do we have some time this morning?”
“All the time you want.” I turned and lifted her on top of me. Feeling her soft sexy body laying on mine made me feel warm and content. She sat up and I took advantage of her position to hold her breasts in my hands. Fondling, and squeezing, rubbing my thumbs over her hard nipples. I pulled Chels to me and sucked her left nipple into my mouth. Sucking her nipple, my hands roamed her body. She let my cock rest on my stomach and slid her pussy lips up and down its length. I switched nipples, bit easily, held her smooth ass with my hands as she slid forward and back. Lifting slightly she positioned my cock at her opening and let me slide inside.
“Oh Chels, no better feeling. So soft and warm.”
She leaned down to kiss me, our lips meeting as my cock explored her wet pussy. Chelsea rolled her hips, until my cock found her G spot, then continued letting my hard cock stimulate her pussy, finally sitting hard onto me so that I could reach deep into her. I rolled her over, never leaving the warmth of her pussy, held her hands in mine over her head. Kissing her deeply, tongues wrestling as I rocked forward into her over and over. Chelsea wrapped her legs behind my back allowing me to reach her depths, pushing in and out, now kissing her face, her neck, she was stretched out below me. Feeling myself getting close, I braced my hands on either side and fucked her hard giving her all I had, she spread her legs wider taking me in as her body rocked, her tits bounced, her back arched, then I exploded into her, flooding her pussy with my hot cum, holding her to me as every drop was pushed inside. Breathing heavily, loving every moment, I hugged Chelsea to me and was rewarded with her smile.
“You’re quite the vigorous lover, Brent. I like it. So forceful.”
“You bring out the best in me”, as I collapsed alongside her. We snuggled in the afterglow of our lovemaking. Light kisses, caresses.
“I could do this all day Chels, but there is a checkout time.”
“Oh boo. Maybe another shower first?”
“I can be convinced.”
The warm water cascaded off of me. The glass door slid open and Chelsea joined me. The sight of her beautiful nude body causing a tingle in my groin and a slight lengthening of my cock.
This wasn’t going to be quick shower.
“MMM, nice and warm lover boy. I had a bit of cleanup to do. That felt like a gallon of your stuff running out of me.” Chelsea wrapped her arms around me and sighed. We soaped each other up, enjoying the excuse for touching each other all over. Chelsea’s breasts could never have been cleaner, now her butt was getting the deluxe washing. I soaped her up then caressed and squeezed her cheeks. When my hand went between them I found her puckered anus and since I was soapy, I pressed with a finger.
“Oh, hello there. I’m not sure if I’m ready for anal stuff, but…” Fair is fair so Chelsea soaped up a hand and pressed a finger against my ass. Naturally I tensed too. We held each other close, each with a finger exploring around the other’s asshole. My cock quickly got hard.
“Brent, is that because I’m fingering your ass, or because you’re fingering mine?”
“Both I guess. But I think I owe you something this morning.”
I got down on my knees, lifted one of Chelsea’s legs over my shoulder and spread her pussy wide open. I stuck my tongue into her opening, then licked up the length of her slit to suck on her bud. She gasped and leaned her hands against the wall for support as I tongued her pussy and fingered her ass. I worked one finger in as I sucked on her clit. She ground her pussy into my face as I flicked my tongue on her clit them licked all around it, then down to her open pussy. I stuck my tongue in as far as I could reach letting her hump my tongue as I fucked her ass with my finger. I continued this dual assault until I felt her tensing against me. I returned my tongue to her clit and licked it as she rode my face through her orgasms. I held her as she came down, panting, breathing heavily, hugging me tightly.
“Brent, that was so different. Powerful. Wow.”
“I’ll do anything to make you feel good Chels.”
“Well keep it coming, lover. Now, give me that big cock one more time before we leave.” Chelsea turned and leaned against the wall, spreading her legs to allow me full access. I got behind her and fed my hard cock into her pussy. I held her hips and thrust forcefully into her. Reaching up I squeezed her rocking breasts and pinched her nipples. She moaned and said, “Fuck me hard Brent.” I listened. Pumping my cock into Chelsea’s begging pussy, long hard strokes until I was ready. Then I pulled her to me, buried my cock in her and shot another load. I held myself there not wanting it to end. I slid my hands up and down her sides, cupped her breasts, kissed her back until finally my spent cock fell from her.
We finished cleaning ourselves and got ready to leave our love nest. It was finally time to go home.
When I dropped Chelsea off, she opened the door. The family was waiting. Accusing? It was uncomfortable. I knew they knew what I’d been doing with their daughter.
“Mom, don’t say a word. I’ll tell you all about dinner. Just dinner. But I had the most amazing night ever.” She kissed me and I went on my way.
There’s only one first time. Sometimes it’s worth waiting for.