First Time Fears (18+)
Request: Could you do a request for Will Halstead where the reader is nervous about sleeping with him since she's still a virgin if that's okay with you
Pairings: Will Halstead x Reader
Warnings: fluff, angst, smut
Masterlist
A/N: thank you @bellarkeselection for requesting it. I love Will and wish he got more love.
A/N 2: @talesofreading and @imagine-all-the-fandoms prepare yourself it's a steamy one.
It's funny how fear can stop you from doing things that you really want. For example, you want to sleep with your boyfriend, Will Halstead, but the fact that you are a virgin and scared to get too intimate with him has stopped you. Stopped you every time. You're so self-conscious about it that whenever it gets brought up or you get to that point you close up and run away. You hated that you got this way. Will is a lovely boyfriend. He takes care of you when you're sick or just had a bad day. He cooks most of the time, you cook too but it’s not as good as his even if he goes on a health kick. It didn’t help that you worked with his brother and he kept asking how your relationship was with Will, it was lovely you had nothing to worry about but it tends to freeze when it comes to intimacy. You met Will when you and Jay Halstead, Will’s brother, had gone to the hospital to question a witness that had been brought in after an attack. When you both looked at each other you both knew it was love at first sight, from that day on you both exchanged numbers and began talking and about 4 months of talking and him taking you on dates he asked you to be his girlfriend and you said yes.
Currently you were out with your friends that you had come to grow and love when you moved to Chicago 8 years ago. You 3 had been chatting nonstop about everything and then it came to the topic of sex. Audrey was married to an accountant, Samantha was engaged to a teacher, and Jenna had a mechanic boyfriend and of course there was you who had a doctor boyfriend, everyone was jealous of you since you had a doctor as a boyfriend. “Oh my gosh Josh and I had the best sex last night.” Audrey said.
“Oh, do tell.” Samantha said, propping her elbows up and sipping her coffee.
“He tried this new thing with his tongue and oh my gosh it had me seeing stars.” Audrey said as the others leaned forward to listen but you sat back and became quiet.
“Did you do anything to return the favor?” Jenna asked
“Oh, you know it.” Audrey said and now you were hoping for a phone call to be called into work not wanting to spend another second talking about sex life. You wanted to have sex with Will but you were afraid, afraid that something would go wrong and that it would hurt. You knew it would hurt some but after reading people’s experience online and some said that they didn't recover for a month you got scared and clammed up. “So, what about you and Will?” Audrey asked and you were so out of it that you didn’t even hear your name.
“Huh?” You asked
“I asked how your and Will’s sex life was.” She said and everyone was now looking at you and suddenly you became self-conscious.
“We haven’t had any sex yet.” You said and they all gasped.
“Are you two, ok? You’ve been together for 7 months?” Samantha asked
“It’ll be 8 months this Wednesday. We’re good, everything is great. We’ve both been so busy. Me working a huge case and him having multiple night shifts we just haven’t found the time.” You said even though most of it was a lie but also the truth. You weren’t going to tell them you’re a virgin nobody knew except your doctor. There is nothing wrong with wanting to wait or being a virgin but it doesn't help your self-consciousness any. Before they could even answer your phone was buzzing and you grabbed it and it was Jay telling you that you needed to come in. “I’m sorry to cut this short but I have to go to work.” You said and everyone protested. “Hey, someone has to keep this city safe.” You said chuckling.
“Fine, you get a pass. Now go and keep our asses safe.” Jenna said and you chuckled and got up and placed some money down for your share.
“I’ll text you all later. Bye!” You said as you put on your coat because of course it was snowing.
“You better or I’m hunting you down.” Samantha said and everyone chuckled but agreed.
“I will.” You said
“Good now shoo.” She said and you smiled and hugged them and then you were out the door. You pulled out your phone and called Jay.
“You saved my ass.” You said when he answered and he chuckled.
“You’re welcome. You on your way?” He asked as you got to your car.
“Yup, just got into my car.” You said as you opened your door and got in and shut it. You got your keys and turned the car on and was met with the heat.
“Good. Be safe getting here. Roads are slick.” He said and you smiled.
“I will be. See you in a second.” You said
“See you.” He said and then you both hung up the phone.
You pulled out of the parking lot and headed off towards the precinct. You slid a few times but nothing to cause you to lose absolute control of your vehicle. When you arrived in the parking lot you sighed and stayed there for a minute and then your phone was ringing and you were quick to find it and look at the name and you smiled when you saw that Will was calling you.
“Hey, Babe.” You said smiling.
“Hey, Baby. Are you still out with your friends?” He asked and you could hear rustling around in the background and you wondered what he was doing.
“No, Jay called and said I needed to come into work. What are you doing?” You asked, curiosity getting the better of you.
“I am getting stuff to make for dinner tonight. I was calling to see if you needed or wanted anything specific. Are you going to be home tonight?” He asked
“I’m hoping so. As for anything I need, I can’t think of anything so you’re good there.” You said
“Sounds good. Be safe please. I don’t want you getting hurt anytime soon.” He said and you chuckled.
“Noted, Dr. Halstead.” You said knowing it drove him crazy when you called him that sometimes.
“Behave yourself.” He said and you chuckled.
“I love you. See you at home.” You said
“I love you too.” He said and then you both were hanging up.
You sighed but now you were in a better mood. You got out of your car and headed up to the steps of the precinct. An officer was quick to open it for you “Thank you.” You said to him and he smiled.
“No problem, Detective Y/L/N.” He said and then you both were quickly parting ways. You looked up and saw Trudy standing at her desk.
“Let me guess you got called in with the rest of them.” She said and you nodded.
“Looks to be that way.” You said “It was supposed to be my day off but crime never sleeps it seems.” You said chuckling and she chuckled too.
“Never. I’ll buzz you up.” She said and you smiled and nodded and walked to the gate as it made a buzzing noise and you were able to turn the knob and pull it open.
“I can’t wait for them to put a keypad in.” You said
“Me and you both.” She said as the door closed behind you and you ascended up the stair where you were met face to face with Jay.
“Took your sweet ass time.” He said and you rolled your eyes.
“Sorry, I was talking with your brother.” You said and he chuckled.
“So, how was the brunch with your friends?” He asked as you stepped onto the floor of the bullpen.
“They started talking about their sex life. So, you really did save my ass.” You said and he chuckled.
“Sooo, how is it?” He asked, smirking and you hit his arm.
“That is none of your business.” You said glaring at him.
“I’m kidding. I’m kidding. I don’t want to know how my brother is in bed.” He said and walked away. If he only knew that you and Will haven’t had sex because of your own silly, to you, fear he would’ve laughed in your face. You went to your desk and took off your coat. You had your gun and badge on your hip, you put them there when you got ready to come into the precinct. You were just hoping whatever you needed to be called in for went by quickly so that you could get back to you loving boyfriend and maybe someday your fiancée. As you took a seat and started your computer and booted it up you looked up at Jay at his desk.
“So, what are we doing here?” You asked. Everyone had been working on a drug bust but activity seemed to have died down so it was put on hold.
“The huge drug bust we were working on has new activity like major activity. We also got new information about it so it’s all hands-on deck again.” He said while looking at you.
“Is there any chance that we are going home tonight?” You asked
“I’m hoping so.” He replied and then Hank Voight walked in and everybody looked up at him.
“Alright everyone gather around!” He said and everyone did. “We just got word that a drop will be happening in 30 minutes. We need to get there before it happens. Jay and Y/N I want you to take the front, Adam and Kim, I want you to take the side, Antonio and Kevin take the other side. Alvin and I will take up the rear.” He said and everyone nodded.
“Yes sir.” Everyone said in unison and headed out. As you got into the truck with Jay and put on your vest quickly as did, he, he started to drive to the location. The truck was filled with small talk until he pulled up to the spot but stayed out of view.
“You know what sounds nice right now?” You asked
“What?” He asked
“My nice warm bed.” You said and he chuckled.
“Cuddled up with my brother.” He asked and you hit him on his arm. “Am I wrong?” He asked, chuckling and you waited a beat.
“No. You're not wrong.” You said and he chuckled “Hey, I think it's about to go down.” You said and pointed to the scene in front of you. “Call it in. I'm going ahead.” You said as you got out and slowly and quietly closed the door. Jay was quick to call it in and then he was following you to your crouched position.
“On my command.” Hank said through the radio.
You waited and waited until it finally went down and he gave the command everyone moved in. “Chicago PD!” Was yelled throughout the group and the criminals put their hands up and everyone was arrested. 20 people in total were arrested and several pounds of drugs were confiscated. Overall, it was a great bust. Everyone high-fived each other. You were just glad no shots were fired and nobody got hurt. Soon everyone was heading back to the precinct and doing paperwork and finally around 8:00 PM you were heading home.
“Finally! I’m escaping while I can.” You said as you were putting on your coat and everyone chuckled.
“Go. Get. Before you’re stuck here. Tell Will I said hi.” Jay said and you smiled.
“I will.” You said and started to walk out of the bullpen and down the stairs you opened the gate and smiled at Trudy. “See you later.” You said and she actually smiled.
“See you later.” She said and then you were out the door and heading to your car as you were doing so you pulled out your phone and called Will.
“Hello, Gorgeous.” His voice came through.
“Hello, Handsome.” You said and he chuckled “I’ll be happy to report that we were successful on the drug bust and I’m heading home.” You said while getting into your car after you unlocked it.
“Good. I can’t wait to see you. I’ll get dinner started.” He said
“Awww, Will. You don’t have to do that. I’m fine with leftovers.” You said
“Not acceptable. My girl needs a meal for a job well done.” He said
“There is no changing your mind is there?” You asked
“Nope. Now get home safely.” He said and you chuckled.
“I will. I love you.” You said
“I love you too. See you soon.” He said
“Very soon.” You said and then you were hanging up the phone and driving out of the precinct and onto the main road and to your shared home. Maybe tonight you’ll get over your fear and finally have sex with your amazing boyfriend.
20 minutes later and you were pulling up to your shared apartment and parking beside his car. You shut the engine off and got out locking it. Bitter cold slapped you in the face and you quickly walked into the building and the elevator and pressed the button. It opened and you got in and pressed the button for your floor. The doors shut and it quickly took you to your floor which luckily was the 2nd floor. You got out and walked to your door and unlocked it and the smell of your favorite meal hit you. “Welcome home.” Will said as he met you at the door and kissed you and helped you out of your coat.
“It smells delicious in here.” You said and he smiled and he chuckled.
“Only the best for my girl.” He said and kissed you until you were breathless until he pulled away when the oven beeped.
“Oh, your brother said hi.” You said and he chuckled and shook his head.
“Go and change. I’ll have dinner on the table by the time you are out.” He said and you smiled at him. He was truly too good to you.
“How did I get so lucky to have you?” You asked before taking off to your bedroom.
“I ask that to myself about you. I’m just glad you stumbled into my ER with a concussion and a gunshot wound with my brother right behind you.” He said and you smiled.
“Though I’m not happy how that situation came to be, I’m glad it led me to you.” You said and then you were heading to get changed and put your gun and badge in the safe and once you were changed and walking out, he had food and drinks on the table. He pulled the chair out for you and when you set down, he pushed you in and then he sat down in his chair. You took a bite and practically moaned and closed your eyes so you didn’t see Will having to adjust his seating or look at you with the most love someone could have for their partner. “This is delicious.” You said after swallowing and opening your eyes smiling.
“I’m glad you love it.” He said smiling and he took a bite of his. The rest of dinner was eaten in silence but he still had a problem especially with all the moaning you were making. Finally, dinner was done and you leaned back in your chair. You suddenly got up and walked over to him and he turned and you sat on his lap and brought him for the sweetest kiss ever and he kissed back. You could feel his boner and you deepened the kiss. You both kissed each other furiously until you both needed air and you looked each other in the eye as you both panted. You wrapped your arms around his neck and leaned your forehead on his.
“Let’s take this into the bedroom.” You said and smiled and gently got up with you in his arms and started to walk towards the bedroom. “I love you.” You said and he smiled.
“I love you too.” He replied as he gently laid you on the bed and got on top of you. He brought his lips to the side of your neck and you turned your head for him to get a better access. He kissed it slowly and passionately, occasionally nipping and then soothing it with his tongue, it made you moan and clutch onto the bedding.
“Mmmm Will.” You moaned out and he smirked against your neck. His hands went to the hem of your shirt and he momentarily looked up at you and you nodded giving him permission. He pulled your shirt up your body and over your head. He tossed it somewhere as you laid topless in your bra, you started to get nervous. Will started to kiss down your chest and down the valley of your breasts and down to your naval. He got to your jeans. “Stop.” You said but he must’ve not heard you “Will, please stop.” You said louder and pushed on his shoulders and he did and looked up at you sitting up slightly.
“What? What’s wrong?” He asked
“I can’t do this.” You said and he sighed.
“What is going on? This isn’t the first time you have done this.” He asked
“I’m…I’m a virgin.” You said quietly and embarrassed and you expected him to be disgusted and be done with you, you expected him to laugh but when you didn’t hear him leave or laugh you looked up at him.
“There is nothing wrong with that.” He said and you sighed.
“I know but it’s embarrassing.” You said and shook his head.
“There is nothing to be embarrassed about. We can stop if you want.” He said and you shook your head.
“No, I want to lose it. I want to lose it to you.” You said and he smiled.
“I would be honored being your first time. We can take this at your pace.” He said and you nodded as he started to stroke your sides lovingly and tenderly.
“Please be gentle.” You pleaded and smiled and leaned up to kiss your lips.
“I promise.” He said against your lips and you nodded and he leaned back and took off his shirt showing his ripped body and his amazing abs. You leaned up and touched them and felt them flex underneath your touch. “Like what you see?” He asked, smirking, this wasn’t the first time you’ve seen him shirtless but each time it took your breath away you never expected a doctor to be so ripped.
“Absolutely.” You said and he chuckled and then started to unbuckle his belt and undo his pants. You watched him practically drooling and almost whined when he got off the bed but when you saw him pushing his pants and underwear down to release his leaking angry red cock you kept quiet. You’ve seen his cock before; you’ve given him plenty of blowjobs so seeing it was no surprise. He got back up on the bed and reached behind you as you lifted up so he could undo your bra and slide it off of you, when you were exposed to him you quickly tried to cover up but he stopped you.
“You have nothing to be shy about. It’s me.” He said and you nodded and he continued to unbutton your pants and undo the zipper and pulled them down along with your underwear and off of you. Now you were truly exposed to him and he was fully exposed to you. “You’re so beautiful.” He said and you blushed and turned away. “You still, ok?” He asked and you nodded “I need a verbal answer, Baby.” He said.
“I’m ok. Please don’t stop.” You said and he smiled and nodded and leaned down and kissed your lips and you kissed back. His hand traveled down your body until it got to where you needed him the most. His other hand was by your head stroking your hair. He touched your clit and you jumped.
“Shhh, I got you.” He said against your lips as he started to circle it, rubbing it, and pulling on it. You started to feel good and started to let out moans into his mouth. He then slid his hand through your folds and down to your entrance and he started to put a finger and you tensed up and he stopped when he felt it. “Hey, it is ok. I got you. We can stop if you want. Just say the word.” He said and you shook your head.
“No, no. Keep going.” You said and he nodded and watched your face as he slid his finger in further until he felt resistance and your breath caught in your throat. He stopped and you nodded and he slowly slid a finger into you and it felt weird and he stayed there for a minute until you nodded and he started to move it back and forth the pain went away and pleasure started to take over and you moaned. Just as you were about to cum, he pulled out gently. “Hey!” You said looking at him glaring and he chuckled.
“I wanna taste you. I want you to cum on my face.” He said as he slid down to come face to face with your slick folds. You were about to say something but he licked a broad stripe of up your folds and you moaned loudly. This was the first time he had ever gone down on you and you wonder why you never let him do it before. It was magical. Your hands went to his red curly hair and gripped it. He ate you out like you were his last meal. You would have closed your thighs around his head but his broad shoulders were keeping them open.
“Fuck, Will!” You moaned and that caused him to go faster and started to tongue fuck you and occasionally he would come up and give you clit attention biting, swirling, and sucking on it. You were close and you started to clench around nothing. “Fuck, I’m close! I’m close!” You moaned out and then he was speeding up his efforts until that knot in your stomach exploded and you were cumming on his face and he was lapping it all up like a dog would water on a hot day. Your grip on his hair tightened as he lapped up your juices through your high. When you did come down from your high and sat up making you let go of his hair. “Fuck, Will. That was so good.” You said and he smiled and you could see your slick covering his chin. “Why I haven’t let you do that until now is beyond me.” You said and he chuckled again.
“I will always make you feel good and make you cum. You don’t have to worry about that.” He said and he smiled.
“I know.” You said and then he leaned forward and kissed you. You could taste yourself on his tongue as he French kissed you. You had to admit you tasted sweet. You both broke the kiss when air was needed.
“Are you ready?” He asked and you nodded.
“Yes.” You said and he grabbed his angry hard thick cock and positioned it at your entrance. He ran his cock up and down your folds and then slowly pushed into your entrance and when you felt it hit that resistance you tensed and he stopped.
“We’re taking it at your pace.” He said
“I’m ok. Go on.” You said and he nodded and rocked forward until he pushed all the way in and you felt a snap and you tensed up. Once he bottomed out, he stayed there. He watched tears fall from your eyes and he was quick to wipe them away.
“Hey, shhhh. It’s ok. I got you. It’ll only hurt for a few minutes but I need to start moving, ok?” He asked and you nodded.
“Ok.” You said quietly sniffling. He nodded and started to rock his hips and pain shot through your body but as he started moving more the pain turned into pleasure and you started to moan.
“I got you.” He said once you got comfortable with it and you wanted him to go faster.
“Faster.” You said
“You sure?” He asked and you nodded.
“Positive.” You said and he obeyed and started to move faster he caged your head in with his arms and his mouth went to your neck.
“Fuck! Squeezing me so tight!” He moaned and your hands went to his shoulders, fingernails digging into them. “So perfect!” He moaned and you moaned with him and panted.
“So big. Making me so full.” You moaned as you threw your head back and to the side and your nails dug into him more and hissed but he loved it. “I love you so much.” You moaned again.
“I love you too.” He replied and then his lips were on your left nipple and that had you letting out a pornographic moan.
“Fuck me!” You moaned as he swirled and licked your nipple. He didn’t stop there as he nipped and tugged on it. Just that alone was bringing you close to the edge and quickly. “Fuck, don’t stop! I’m close!” You said and then he was pulling off your left nipple and giving the right nipple the same attention. During all of that your nails had started to go down his back leaving scratch marks but he wasn’t complaining. Once he felt that your right nipple had enough attention, he pulled off of it and looked at you’re in-awe expression.
“I can’t wait to marry you and fill you with children to watch these-” He started and cupped your breasts “swell.” He said and that had you moaning and closer to cumming. “Cum with me.” He said and released your breasts and brought one hand to your clit and started to rub it and play with it. You could tell he was close by him starting to stagger in his thrusts and you started to squeeze him “That’s right squeeze me. Cum with me. I’m close.” He said and you nodded.
“Me too. Let’s start making a baby now. I want to mother your kids and I don’t want to wait. I’m not on birth control.” You said and that all too familiar knot was back and it was about to snap. That seemed to spur him on because with one last tug on your clit you were cumming hard and then he was too. You both came with loud moans as he painted your walls white. “Fuck.” You said as you started to come down from your high.
“You’re amazing. I can’t wait to have kids with you and be your husband.” He said as he was coming down too. Once you both were blissed out, he slowly pulled out of you and you could feel his cum trickle out of you and you jumped from overstimulation when he pushed it back in. Once it was all back in, he laid on the other side of you. “Were you serious when you said you weren’t on birth control?” He asked and you nodded.
“I haven’t been on it for a while. It was screwing a lot of things up with me.” You said turning to look at him and he slipped an arm under you and pulled you into him.
“Thank you for letting me be your first.” He whispered
“I knew from the very moment we started dating I wanted you to take my virginity. I always got scared when we started to get very intimate and that I would be hurting for months from what I’ve read.” You said and he gave you a look. “I know I know. I shouldn’t haven’t looked it up. I couldn’t help myself.” You said and he chuckled.
“I would never ever hurt you. Ever. I love you too much to do so.” He said and you nodded and smiled.
“I know and I love you too. It was amazing by the way.” You said as you cuddled into him and he started to throw the covers over you.
“Only the best for my girl.” He said and kissed the top of your head. That’s how you spent the rest of the night. In his arms with nothing to worry about. The smell of his cologne and the scent of sex was lulling you to sleep. Your eyes finally slipped closed and breath evened out. Once Will felt your breath even out, he kissed your head one more time and he finally allowed himself to fall asleep. Both not knowing that one of his strong swimmers had made contact with an egg and life was being created inside you.
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