Some people have sometimes thought about what it would be like, but few are strong enough to admit they eventually slept with someone with whom they had a prior close relationship. I am one of those men.
I had no warning about what would lie ahead of me in the near future when I came home from work one evening. My girlfriend planned to attend a charity benefit that she’d nagged me for weeks to go with her, and I was already running late. I don’t mind helping important causes, but I can’t sometimes help but wonder if Morgan is more interested in being seen by the “right” people to help her up the career ladder than sincerely caring about the specific charities.
I knew something was amiss when she was already dressed for the benefit when I walked in the door. In our entire time together, Morgan was NEVER ready to go anywhere before I, but she still looked like the stunning former beauty queen I’d fallen for in high school.
“Let me get a quick shower,” I said. “I’ll be ready in twenty minutes.”
She shook her head. “Don’t bother; I’m going to handle tonight alone.”
“Wait…what? You’ve been busting my balls for weeks to go with you, and now I have to stay home?”
“It’s not that simple. We have a surprise tenant. Since I’m already listed in tonight’s program, you can entertain her.”
“Chelsea. She’s moving in with us to be closer to her college.”
“Your little sister’s already in college? I remember when she was just starting fourth grade.”
Morgan smiled. “She’s looking forward to seeing her ‘surrogate big brother’.”
“Maybe hanging out at home isn’t such a bad idea. That little girl and I have some serious catching up to do.”
“Admit it, Tom; you didn’t want to go out in the first place, and my sister’s hardly the little girl you remember.”
“I think you were the only guy besides Dad who was ever decent to Chelsea in her entire life.”
“Well, yeah; she’s the baby sister I never had. Someone has to look out for her, probably more now that she’s becoming a woman.”
“Before you go into overprotective big brother mode, she’s a virgin and not seeing anyone.”
“Uhhh…too much information?”
“No raiding the liquor cabinet either, mister. She’s only nineteen.”
“Yes, Mother,” I replied with an eye roll.
Morgan gave me a kiss. “Keep her entertained and there may be a little something in it for you later.”
I squeezed her firm ass cheeks. “Mmm, baby, I’ll be waiting in bed naked and hard. It’s not like we have much fun in the bedroom these days.”
She pulled away my hands and turned to leave. “Behave. Go say hi to Chelsea, and I’ll see you later.”
The sounds of music and drawers and closets closing in the guest room filled my ears after coming upstairs. Despite what Morgan told me earlier, I still expected to see a shy, chubby girl with glasses and a mouthful of metal when I appeared in her doorway.
Instead, I was treated to the vision of a young woman at least five feet tall with shimmering blonde hair to her shoulders. Chelsea’s a bit more curvy than what passes for acceptable in our society, but everything settled into a perfect 34D chest like her sister’s, voluptuous hips, and a beautifully rounded ass. The only difference between both sisters was that Morgan’s tits were “store bought” while Chelsea’s were courtesy of nature.
“Do I know you, miss?” I teasingly asked.
Chelsea turned and leaped into my arms. “Tommy!”
I laughed and gave her a tight hug. “Hey, baby girl.”
“‘Baby girl’ my ass,” she snorted and removed herself from my grasp. “I just turned nineteen and in college.”
“I’ve been informed as to such; that and you’re going to be living with me and your sister for a while. I’m not sure if I can handle two beautiful women under the same roof.”
“Oh, stop it! I don’t know what you did to her the last ten years, Tommy, but it’s a breath of fresh air to know Morgan’s no longer the self-absorbed bitch I dealt with growing up.”
“There’s an eight-year age difference between you two, Chels. Maybe she wanted a baby brother and resented having another girl in the house.”
“It still didn’t excuse her calling me Chelly the Four-Eyed Hippo, making fun of my braces, talking shit about me never getting a boyfriend because I was so hideous, and acted like she was embarrassed to be seen with me in public. Not every girl grows up winning one pageant after another and having every boy in town fawning over her while some of us remained practically invisible.” She then laughed. “I did get some justice, though; my hair stood blonde and these boobs grew on their own while Morgan’s hair darkened and she had to get implants.”
“You became a beauty,” I assured her.
“You’ve always been way too nice to me, Tommy. I may be young, but still smart enough to know the world’s Chelseas rarely get edges over Morgan types.”
“Don’t be so sure. You’ll have plenty of time to meet the right guy. Concentrate on your education first.”
“Now you really sound like a big brother!”
“I resumed where I left off because I care about you.”
She stood on tiptoe and pecked my cheek. “You’re so cute. I thought you were going with Morgan.”
“Change of plans. She didn’t want you to be lonely the first night in your new home.”
“Let me guess; you weren’t thrilled with the idea of dressing up to eat rubber chicken at some boring charity dinner anyway.”
“You know me well. My idea of a wild night is kicking back in clothes your sister hates seeing me wear, not showering, eating cold pizza, and rotting out my brain in front of the TV.”
“I never took you for the homebody type, Tommy.”
“Thank your sister for dragging my ass almost everywhere the whole time we’ve been together. I’m not complaining, but some ‘me time’ is welcome on occasion. I’m going to sound like a bad boyfriend for saying this, but I was actually relieved when she told me to stay home and keep you company.”
“I don’t think you’re a jerk at all. A little down time alone never hurt anyone.”
“Speaking of which, are you in the mood to hang out downstairs? I planned on popping in one of my dude movies Morgan can’t stand.”
“Yeah, I’ve finished unpacking and could use a break with one of my favorite people.”
Chelsea went upstairs to prepare for bed after the movie ended. I still hadn’t showered since coming home from work, and Morgan was due home in half an hour.
I turned the bathroom door knob to open it when the sight of a topless Chelsea made me freeze in my tracks.
She screamed and quickly covered her bare breasts with a towel. “Damn it, Tommy!”
“Oh my God,” I gasped in embarrassment and backed away. “I am SO sorry!”
“You better not have walked in on purpose! It’s not funny!”
“Who’s laughing? I swear, Chels, I didn’t know you were in here.”
“Try knocking next time, dumb ass.”
“Again, my mistake. I’m sorry.”
I hurried into the bedroom feeling both aroused and mortified, hoping Chelsea wouldn’t say anything to Morgan about our awkward bathroom meeting. My concerns went unfounded; by the time she arrived home, I finally had my shower and was settled in bed.
Morgan immediately spied my still-present erection that formed a tent under the covers. “Wow, I guessed you’d be naked and waiting, but didn’t expect THIS much interest!”
“I’m ready to collect on your early promise, baby,” I said, omitting the unexpected eyeful I’d gotten of her sister’s tits.
She undressed and stood before me with a sly grin. “I hope you put on a condom.”
“I’m well familiar with the rules after ten years. Now get your sexy ass in bed.”
Morgan tossed back the covers and slid in beside me. I opened her legs, inched down, and buried my face in her neatly trimmed pussy, sucking her lips into my mouth as my tongue darted in and out. The taste of her sweet nectar drove me wild and I sucked harder, stopping occasionally to nibble her clit. I love eating pussy and enjoy watching a woman get off while I’m doing it.
“Ohhh, God, Tom! That feels so good, but I need a good fucking NOW!”
I reluctantly broke the suction, withdrew my tongue, rose from between her legs. I positioned myself above her gorgeous, almost flawless body and guided my entire length into her.
“God, baby… this was worth the wait,” I said between labored breaths. I clenched my teeth and struggled to both control my lust and remind myself not to call out Chelsea’s name as Morgan and I started fucking at an almost breakneck pace.
She reached between her legs and began to rub her swollen clit as I thrust in and out of her. “I’m really close. Please, Tom, don’t stop.”
I quickened my pace, pushed deeper, and felt the head of my cock repeatedly jam against her cervix. Morgan began to tremble and air expelled from her lungs with each of my thrusts. Her pussy convulsed in orgasm, taking me to the edge. She shuddered and cried out my name as I peaked. Lost in the sensation, I shot my load.
I collapsed beside her when my euphoria subsided.
“Wow, baby!” I exclaimed.
“Wow is right! I can’t remember the last time you were so enthusiastic during sex. What brought that on?”
You don’t want to know, I thought. “Maybe thinking about you in bed with me after hobnobbing with all those hot guys at the benefit got me going.”
“God, I hope Chelsea didn’t hear us.”
“She had a long day and probably dead to the world. Moving into a new place can be exhausting.”
“I worry about her sometimes,” Morgan said. “She probably told you about me tormenting her when she was little, but I really wanted to make up for everything, you know? We started catching up and mending fences not long before I invited her to live with us.”
“Yeah, she and I talked earlier. Letting her move in was a great idea.”
“Chelsea’s so brilliant and pretty, but it bothers me she’s still a virgin with no man in her life. Who is she saving it for?”
“Baby, she’s nineteen with a whole life ahead of her. What’s the rush?”
Morgan sighed. “I suppose you’re right. Not everyone gets to lose their virginity at sixteen like I did. Being tired clouded my thinking.”
“I wore you out a bit ago, didn’t I?”
“Don’t flatter yourself, Tom. I had a long night on my feet.”
I got out of bed to use the bathroom. “Then maybe you should get some sleep. I’ll be back in a few.”
The bathroom was now dark, so there was no chance I’d again startle anyone. I shut the door, disposed the used condom and began stroking my newly erect shaft, mind focused on images of Chelsea’s naked, well-endowed chest. It didn’t take me long to come, which created a mess I quickly cleaned up before taking another shower.
Morgan had a point; why was Chels saving herself when she never mentioned wanting to get married? For a chance to fuck some loser frat boy in back seat of his car just to be tossed aside and forgotten afterward? To climb between the sheets with an older married professor to whom she’d be nothing more than a young piece of ass until she graduated? To be talked into a gang bang by some horny jocks with hopes of becoming popular?
No way. Not if I had anything to say. Her first time should be a far more pleasant experience.
Then I thought of an idea…but it would take the right opportunity for me to put a plan into action.
Morgan went out of town the following week to judge a pageant, which once again left Chelsea and me alone. We didn’t see each other much during the day; I usually had to work until early evening and Chelsea carried a full class load, earning top grades as a chemistry major.
When some of my co-workers dropped me off one Friday after they and I had gone for a couple after-work beers – something else Morgan frowned upon – Chelsea was already home.
Delightful smells of Italian cooking invaded my nostrils upon opening the front door. She was busy stirring a pot on the stove and greeted me with a smile.
“There you are!”
I gestured at the pots and pans. “What’s all this?”
“Dinner. Don’t tell me my dear sister doesn’t cook.”
I shook my head. “Unless it’s frozen, packaged, canned, or comes from a crock pot. Not that she eats much anyway.”
Chelsea poked my middle. “That explains your little tummy pouch. Too much processed shit and not enough home cooking.”
“Yeah, maybe I should hit the gym more often, nix the junk food, and cut down on beer.”
“I think your pouch is cute.” She raised a spoon to my lips. “Here, I need a second opinion.”
The sample she offered was a taste of heaven. “Wow…beauty, brains, and a great cook. A guy will hit the jackpot with you someday.”
“Saying the sauce was okay would’ve been enough. Everything’s almost ready. Do you have any decent wine?”
“Let me check, but I’m under orders not to serve you.”
Chelsea gave me one of her “are-you-serious” looks. “Jesus, Tommy. Does she really have a tight squeeze on your balls?”
I put two wine glasses on the table and grinned. “The hell with it; let’s share a bottle. What Morgan doesn’t know won’t hurt her.”
“Now you’re talking. It’s not like I haven’t had an occasional beer or two on campus. I’m not innocent, boring, and lily white as my big sister thinks, but I don’t go overboard either.”
“Thank God; you had me worried for a second. I’ll go get that wine.”
Chelsea had everything on the table when I returned with a vintage bottle my parents sent for my birthday. We enjoyed it with the pasta dinner she cooked while chatting about her college courses and my job.
“I wish the current you had been around when I had to take chemistry in high school. I ended up failing. Morgan still laughs about how lucky I was not to blow up the lab and God knew what else.”
“YOU failed chemistry? You’re so smart; I can’t see you failing anything.”
“Well, I wasn’t the world’s most diligent student or the best-looking one, for that matter.”
“Come on, Tommy; now you’re being silly.”
“Morgan never told you about her going to the prom with me out of pity?”
“I know she was a real bitch back then, but can’t imagine stringing along someone like you. Most of her other high school boyfriends were jerks. You’re the only one I liked.”
“Well, imagine the tall, lanky, eighteen-year-old Tommy you adore so much battling acne and out of control curly hair being chosen by the class beauty queen for the prom when she could’ve had anyone.”
“I still say it wasn’t a pity date. You guys stood together for little over ten years, but I do have a burning question.”
“Fire away, baby girl.”
“Why didn’t you ever marry?”
“Chels, your sister and I don’t need a piece of paper to prove anything. Morgan’s fine with the way things are.”
“Well at least make me an auntie in the near future.”
“She’s not big on the idea of having kids.”
“Don’t you want a family?”
“Maybe…but a little late for me, isn’t it?”
Chelsea rolled her eyes. “You’re only twenty-nine! There are guys out there who are forty and older having kids. One of my professors is at least forty-five just had a baby with his wife. Of course, she’s like around Morgan’s age, but-“
“I get it. Let’s talk about something else.”
After dinner, we settled into the living room to watch another one of my “dude movies” Morgan detested. Chelsea eventually dozed off, likely from the wine. Her head soon landed on my shoulder, but looked so peaceful I didn’t bother moving her.
I became tired shortly before the movie ended and wanted to go to bed. I gave her a gentle nudge.
She woke with a start. “What? What?”
“You fell asleep during the movie. I need to go to bed.”
“Not a bad idea,” she replied with a yawn. “Glad I don’t have classes tomorrow. I think your wine did a number on me.”
I couldn’t help but chuckle. “Lightweight.”
“Oh be quiet, smarty pants. I’m going upstairs to take a shower.”
“Think you can make it or should I carry you?”
Chelsea gave my arm a playful punch. “Shut up! I’ll be fine.”
“Okay, baby girl. I’ll see you in the morning.”
She gave me a wink. “Don’t dream about anything I wouldn’t.”
Chelsea was left alone most of the following day until late into the night since I had to work a second shift. Turning into the cul-de-sac that led to our house, a sense of panic over came me after spotting two police cars parked in front.
I sprinted from the car. “What’s going on?”
“Sir,” an officer said, “you need to stay back.”
“I own this house, and my girlfriend’s sister is in there alone,” I informed him. “I need to find her.”
A piercing cry of “Tommy!” filled the air before he could respond. Chelsea ran over and enveloped me in a hug.
I held her tight. “Chels! What the hell happened tonight?”
“I went to the library around six to study and then met some friends for coffee,” she answered in a shaky voice. “The front door was wide open with two men inside when I got back. I must’ve forgotten to lock up…I-“
I buried my face in her hair and stroked it. “Shhhh…don’t be hard on yourself.”
“Morgan will kill me if anything’s gone.”
“I’ll deal with her when she comes home. Did those guys try anything with you?”
“No, no; neither saw me before I ran next door and called the police.”
“Good; I’m just glad you’re okay.” I slowly pulled away from her. “Let me talk to the officers and see what they have to say. Stay here.”
“I’m not going far, baby girl.”
Her gaze remained fixated on me the entire time I sorted out what exactly happened in the house. Nothing appeared to be missing; other alert neighbors swung into action soon enough to prevent a far worse fate – such as Chelsea being raped and/or murdered. Something or someone was definitely looking out for us.
We were advised to stay somewhere else for the night. I checked my phone for motels, and settled on one located twenty minutes away. We threw together a few items and left while the police wrapped up their work for the night.
Things became awkward at the motel…least at first.
A mixup in our reservation resulted in the room having one bed instead of two. I offered to sleep in the car, but Chelsea insisted I stay inside.
“Are you crazy? You paid for this room and shouldn’t sleep outside like a dog, Tommy. Trust me; I’ve seen guys in underwear before.”
“It’s only right to be a gentleman after the room mix-up.”
“Don’t stress; it wasn’t your fault and we’ll only be here tonight. Are you done in the bathroom? I want to get ready for bed.”
“It’s all yours.”
“Are you hungry? I could get us something.”
“No, I’m good.”
“Okay. I’ll be watching TV if you need help washing your back,” I teased her.
“Oh, Tommy! You’re so silly.”
“Can’t say I never offered.”
I undressed, crawled in bed, and flipped the TV remote before settling on a sports channel. I must’ve fallen asleep not long after, because I don’t remember seeing Chelsea come out of the bathroom.
It was sometime during the night when an urge to piss woke me. The room was dark, TV off, and Chelsea sound asleep beside me.
I walked back to bed after finishing in the bathroom, noticing moonlight from a nearby window across her slumbering figure. Chelsea wore only a T-shirt hiked up enough to show a little midriff and lacy white bikini panties, and I couldn’t recall a vision so beautiful since the first time Morgan and I slept together.
I knelt by Chelsea’s side of the bed, gazed at her, placed a hand on her leg and gently stroked its soft skin for several minutes. Her breasts were tempting under the T-shirt, and I gave each a small squeeze before my hand trailed down her stomach and stopped between her legs.
A pleasant surprise greeted me when I pulled aside her panties; the sight of Chelsea’s hairless mound was inviting. She stirred-but didn’t wake-as I stroked her clit and slipped two fingers into her wet opening. My spare hand massaged one of her bare breasts while I continued slowly finger fucking her.
My erection ached to be free of the fabric that restrained it. I stood, removed my underwear, and climbed in bed beside her, planting soft kisses on one of Chelsea’s breasts and neck and slipped two fingers back inside her pussy.
A low moan escaped she lips before she finally awakened. Still groggy, Chelsea turned to face me. “Huh? Tommy?”
“Shhhh…it’s okay, baby girl.”
“What’s going on? What are you doing?”
I kissed Chelsea and then muttered in her ear,”I think it’s time to make you a woman.”
“But I’m still-“
“Don’t worry; I’ll go slow.”
“This is just wrong, Tommy.”
“Is it, Chels? Is it wrong to be with a man who cares about you instead of some horny kid only out for one thing before you’re forgotten?”
“You really want to…?”
“Your first time should be nothing less than memorable.”
Before she could protest further, began making a trail of light kisses down her body, stopping with my head between her legs and pulled off her panties. I nibbled on her clit, licked the entire perimeter of her pussy, and then slid my tongue in deep as I could while gently pushing an index finger into her ass.
Chelsea’s body began quivering while I continued giving her the pussy eating of a lifetime.
“Oh my God! What just happened?”
“You had your first orgasm, baby. Didn’t that feel good?”
“The best is yet to come,” I assured her. “I want you so much. Let me make love to you.”
“I don’t know, Tommy; I-“
I positioned myself on top and kissed her. “I promise to be gentle.”
I slowly pressed forward, feeling slight pressure as the head of my cock pressed against her hymen. Chelsea felt pain of it tearing and began to whimper.
“Tommy…please stop…it hurts.”
“It’ll only be a few minutes, Chels, and then feel good. I promise.”
I pulled my cock out until just the head remained and then fucked Chelsea with long slow thrusts while trying not to hurt her further, and then rewarded with the elation of being her first lover. The pained look was still on her face, her breathing fast and shallow.
“Are you ok? Did I hurt you?” I whispered.
I slowly pulled back my hips, my eyes fixed on hers to look for any other signs of pain. I stopped again with my cockhead just at the entrance of her pussy, watching the slight grimace as the crown pushed past the area where her hymen once was. I focused on the feelings emanating from my body, every muscle taut, still trying to overcome the instinct to repeatedly plunge my entire shaft inside her over and over, fast and hard. The desire to do it again and again had become more difficult to resist.
Her breathing was still labored and I thrust harder, gaining slightly more depth. I felt the best sensations I could remember, the joy of sex without the barrier of a condom as I’d done for years with Morgan. Tense vibrations of every muscle washed over me as I kept thrusting in and out of Chelsea’s tight warm pussy.
He whines of pain were replaced by gasps, squeals, and moans of pleasure.
She was having another orgasm!
“Oh…my…God…Tommy…” Chelsea gasped. “I’m having the same feeling as when you licked me!”
“Didn’t I say this would soon feel good?”
“Yes…can you keep going?”
“I’d love nothing more, baby,” I said.
Chelsea wrapped her legs around me and pulled me closer as I thrust deeper inside and proceeded to fuck her long and hard, my head spinning with desire and lust.
Then I felt a familiar tightness in my balls and cock swelling inside her; it was only a matter of moments before the big finish.
“Chelsea…my sweet Chels, my beautiful girl…” I gasped as I started coming inside her. It was almost as if my climax was endless as additional semen filled her pussy until I felt completely drained.
My cock remained buried in her after we finished. I bent down and gave Chelsea a deep kiss before I slowly withdrew and lay beside her.
We held each other for several minutes in silence before I again spoke. “Are you all right, baby?”
“Yeah,” she replied with a giggle. “I can’t believe I just had sex with my sister’s boyfriend!”
“Don’t tell me you feel guilty.”
“Oddly enough, I don’t. I mean, Morgan’s still hot and all, but sex has become less frequent between us, and she still insists on me using condoms the times we do fuck. I almost forgot what bareback felt like.”
I cuddled her. “You were amazing.”
“I’m glad you were my first. You’re right; most of the guys at college would’ve probably dumped me after I slept with any of them.”
“I just wanted this time to be special for you, Chels.”
“And it was. Thank you.”
I pulled the covers over our naked bodies and kissed her one last time.
“No, thank YOU,” I whispered and nuzzled her neck. “We need to get some sleep. Check out time is at eleven tomorrow.”