Shawn Mendes imagines

when you're ready (y/n (love and sex))

shawn pov
It has been almost a year since me and y/n
started dating. As soon as we met I could feel the connection between us. It felt so natural between the two of us. After several weeks of her being on tour with me I decided to make it official with her. When I asked her, she was so happy and thought what I did was sweet. I took her to an amusement park for the day. It was night time and we had just finished watching the fireworks show. While walking back through the park to the tour bus, I asked her if she would like to be my girlfriend. She replied with a "yes." I could tell that she was thrilled and I could tell that she cared. I was go glad that everything worked out.

*some months later*
shawn pov
Hearing y/n say the words "i love you" to me for the first time was amazing. I really appreciate how she isn't like my fans. She is the type of person that doesn't say those words to a lot of people. Instead y/n says it when she truly means it. To the people that are closest to her in life and that are important to her. I never expect or pressure her to say it to me. I am so happy that she was able to reach this point and feeling in our relationship. I replied with "i love you too, babygirl" I know that I say it to practically everyone but y/n knows that with her there is something special and comforting which shows her that I mean the words I say.

* a little after a year of knowing each other*
y/n pov
We were on the tour bus with some of Shawn's friends and the crew. Brian was always teasing us about not doing it. Shawn was sitting behind me tonight when it was said again. He ignored Brian again and the crew rolled their eyes at Brian. Shawn came and sit next to me on the floor putting his arm around the back of me. I looked at him and whispered to him "Shawn I think I'm ready" "are you sure?" he replied. "yeah I am" Shawn knew that this was such a big deal because I've never done it with anyone before. What I loved about him so much was that he didn't care about it and that he never pressured me to do things like this if I wasn't comfortable with it. With that being said Shawn led me into his room of the tour bus. Since everyone was there we just talked for a bit and then went to bed. Fast forward to friday night. We got back home late thursday night to Toronto. Little did I know Shawn had talked to his parents and sister to help him set up a romantic evening for the both of us.

shawn pov
After y/n said that she's ready, I decided to plan something special for us because it's her first time doing this with anyone. I am so lucky that she is allowing me to share this special milestone in her life. I called my parents and talked to them about helping me set up a special evening for us when we get back to Toronto. They were able to set up a date for us along this small private beach about 45 minutes from my condo. My idea was to take y/n out for a romantic, stress free, evening to spend time together. Then when the time came we would make our way into the bedroom of my condo and be intimate. I wanted this moment to be special for her. I didn't feel right about doing it that night on the bus with everyone there since we haven't done it before. The next day Aaliyah faced timed me. I love it when we get to talk because she can't spend the entire tour with me. I asked about her and how she's doing because I care about her and want to protect my little sister. After a little while Aaliyah brought up how I feel about y/n. Our parents must have told her what they planned for us. She asked me if the two of us are going to finally do it. I had a big smile on my face and said "haha" Aaliyah then said "okay, you don't have to tell me." We said "i love you" to each other and then I blew a kiss at her before hanging up. Tonight was the night we were flying back to Toronto. I had planned everything for friday because we would get home too late thursday. y/n was so tired when we got to my condo that she made it as far as the couch. I could tell that she was too tired to move so I got some blankets and snuggled up next to her. In the morning I slowly woke up to the movement from y/n. My arms were wrapped around her. She tried to pull away from me so I pulled her closer. About 10 minutes later we got up. I went to go take a shower. A few minutes later y/n got up and pushed open the bathroom door. We usually don't lock it in but we just close it mostly. I heard her go straight for the toilet. It turns out she had to pee. I forgot that we got home late and went right to sleep. After I was done in the shower, I went into the kitchen to see y/n sitting at the island. She was adorable from behind with her favorite sweats on and my pink hoodie. I went and hugged her from behind saying "I'm sorry for holding onto you this morning when we woke up." She said "it's alright, i love you." I replied with "i love you too, y/n." We decided to make waffles for breakfast. Our day was pretty relaxed, just the two of us basically hanging out. At about 5:00pm I said to y/n I have something planned for us tonight so wear something nice, maybe a dress? She smiled and was shook. I don't think she believed that we were going to do something tonight. I said be ready soon, because we have to leave in 20 minutes. "20 minutes?" I beards from our bedroom. "yeah, we just have to look decent, nothing over the top." "Sounds good to me." y/n loved that we didn't have to go all out or over the top with looks. She'd rather it be more casual but classy kind of thing. As we walked out the door and down to the main lobby, I checked my phone and texted my mom and then dad to let them know we will be gone for the next few hours. We arrived to the date location at about 6:25pm. The look on y/n face was priceless. She was stunned and said "aww... i love it Shawn. this is so thoughtful of you!! you're the best boyfriend i could ever ask for. i am so grateful for you in my life." Before heading back to my condo, we took a walk down the beach and watched the amazing sunset. It was getting late and I messaged the limo to pick us up. On our way home, I could tell y/n got a little more nervous than she was earlier. I comforted her by holding her in my arms and playing with her hair that was gorgeous. Her hair is long and wavy. I love running my fingers through her hair and how it calms her down. As we arrived to the condo I was lookin forward to y/n reaction. I unlocked the door and opened it to dimmed lights, roses, and rose pedals spread all over the counter and on the floor leading to the bedroom. The most embarrassing thing was the condoms laying out on the counter (that must have been my dad's idea). y/n went to the bathroom and when she came back into the kitchen she noticed what was on the counter and laughed. Then I picked her up and placed her on the bed. I started slowly by touching her body. I took off her bra and pulled it out from underneath her cute spaghetti strapped dress. I decided it would be better if we had some clothing on because I know y/n is always cold. I took off her underwear and tossed it down on he ground behind me. I motioned for her to unbelt my black skinny jeans. She got my pants off and then took my underwear off. I carefully layed my body on top of hers without putting too much of my weight on her. We were kissing passionately and I managed to take it to the next step. I was gently touching her down there and she seemed really tense and nervous. I whispered to her "don't worry" and continued my movement carefully. I reached to the nightstand for the condom (i put it there when i first put y/n on the bed). I quickly opened it and put it on not losing sight on y/n. I asked her if she was ready. "yeah shawn i am. " she said very anxiously. As I stroked her hair I said "don't worry baby, if you don't feel good just tell me it's uncomfortable, alright?" "alright " she said.

y/n pov
Shawn is so sweet to plan this night for us to make my first time special. He is so caring towards me. I was so anxious to do this. Shawn was so careful and gentle. It was really uncomfortable but I managed to get through it. I didn't want to ruin the moment we had. I could feel how tense I was with him inside me and felt kinda bad for him. When we were done, Shawn layed next to me and kissed my forehead. "you did amazing baby, i'm so proud of you." he whispered. I said "Shawn are you sure that it was great because it seemed really painful for me" "aww... darling why didn't you tell me. i would've stopped" "because i didn't want to ruin the moment" "next time promise me you will speak up about that because i want you to enjoy this, not hate it" "okay shawn. i will" "is there anything i can do for you babygirl?" "i'm tired, can you get me the blanket at the end of the bed?" "sure of course, good night i love you"

shawn pov
I wish y/n told me how she was feeling. I'm glad that she was comfortable with this and we it to share this moment together. She was so cute next to me all cuddled up.

*next time you guys saw the crew and brian*

y/n pov
"so shawn how was it?" "it was good" he said with a huge smile on his face "really? what did you guys do?" "brian stop!" shawn said before we walked away.  I loved that Shawn acknowledged Brian enough but kept it simple without going personal.