First time I [F] rode my boyfriend [M] TESSA UPDATE ???

Hi everybody!!

Tessa here again :) thankyou for all the kind and lovely comments on my last post, I really appreciated it. Omg also the title?? I don’t know what to call it sorry hahaha

It’s been about a week since Ashton and I have had sex for the first time. For the first two days I was sore but I literally couldn’t stop thinking about doing it again so it’s been a very regular occurrence! Ashton is “over the fucking moon” he says, and I’m pretty happy too haha.

Here’s a note from Ash cause he wanted to say hi ???:

Hey everyone who supports Tess and I! Tessa was really nervous about posting the sex update but she said that she’s gotten nothing but positives. A few people were messaging her and asking if she felt ready and if she was okay. Obviously I’ll let her answer for herself but all I wanted to say is that I love Tess, and I know lots of you guys really care for her so I wanted you all to know that she was supported, loved, cared for and reassured throughout the whole thing. I’ve told her hundreds of times that I wouldn’t care if we waited six months to do it or longer, and the decision was hers (and mine) to do it. Hope you like my girls’ story :)

So as I’m not too ready to tell y’all about the first time, I’m going to be telling you about the second time we had sex. Because I’m not like super duper used to it yet, I mightn’t be amazing describing it because I’m still figuring out how to say how good it feels but I’ll do my best. Also this was the first time that I was on top ? ALSO: I’m on the pill (I have been since I was younger for personal reasons) and we’ve both been tested a weekish before we had sex and we’re both clean. We did have sex without a condom this time but only because we were safe and know the risks and are extremely aware of what we’re doing. Please, if you have an issue with it don’t comment about it as this is a private decision between me and Ashton that was made together. Thanks!!

So it was a Sunday morning, our first time was Friday night and Saturday I was too sore to do anything (he’s big guys, and I’m tight down there sooo). I woke up with my face on his chest and my hand holding his, the sheets tangled between us.

“Hi beautiful” I heard him say roughly, his morning voice apparent. I kissed his bicep and squeezed his hand, closing my eyes. Waking up with someone you love is the best thing ever.

“Someone’s a little tired this morning” he said and chuckled, stroking my hair. I nodded against him and we lied still for a while, him humming softly and stroking my hair still. It was raining outside and dark, which made me so happy because I love the rain!! Feeling a bit more awake I rolled over on top of him, sitting up and straddling him over the sheets.

“Woah, hello there” Ashton grinned and I lent down to kiss him, “hi” I said softly against his lips (woaaaah I’m cheesy) before sitting back up and running my hands over his chest. He was naked, I was wearing just his shirt, the quilt between us.

“What’d you wanna do today?” I asked, tracing my fingers against his skin.

“You” He replied.

I giggled and blushed, running my fingers over his stubble and back down to his chest.

“You’re silly” I told him, blushing because I started to remember the first time, making me squirm a little in his lap.

“You love it” he said laughing and placing his big hands on my hips.

“Love you” I said shyly (we’ve said it before but I still get blushy)

“Love you” He said grinning.

We sat with me on his lap for a while, talking about the dreams we had because we’re cheesy and about 10 minutes of me deciding if I wanted to make pancakes.

“I don’t understand why you’re making me breakfast when all I want to eat is here already” Ashton teased.

“Go awaaaay” I giggled back, lying down on his chest and snuggling back into the crook of his neck. I moved my lips and kissed it, just a little one. Ashton loves neck kisses even more than I do, so I continued to kiss softly, moving my lips over his neck.

“You make a man weak, woman” he croaked out, making me laugh and push myself up to look at him.

“Hey” I said

“Hey” he replied, chuckling

“Wanna do it” I said with all my confidence

Ashton looked at me seriously for a few seconds before breaking out into belly laughter.

“I made our last time so romantic and intricately planned and with candles and everything and now you just want to ‘do it?’” He laughed.

“Well, do you?” I smiled, biting down on my lip and tucking my hair behind my ears.

Ashton slowly calmed down from laughing and studied my face.

“How are you feeling? Are you still sore?” He asked, moving his hands down to the tops of my thighs and massaging them.

“A little, not as bad as yesterday” I told him.

“I don’t want to hurt you Tess” he mumbled.

“I’m okay” I smiled, bending down to kiss him.

“Can we have sex now please” I asked quietly, smiling.

“Fuck, yes yes yes” he said.
“All I’ve been thinking about is being inside of you and how tight you are and when you came on my cock I-“

I put a hand over his mouth, blushing hard. He smiled against it,

“I’m just telling the truth baby” he grabbed my hips and gripped tightly.
“Plus I know how much you love hearing me say things, even if you don’t admit it” he said with a grin (it’s true but I’d never admit to it)

Ashton moved his fingers to the shirt bunches up around my thighs, lifting it slowly. His concentration and the way he looked at me made my cheeks flush as I held my arms up, slipping the shirt off of me. I instinctively moved my arms over my breasts, feeling exposed and self conscious.

Ashton looked up at me, frowning.

“Don’t cover yourself up. Ever ever” he said, trying to move my arms away.

“I just get nervous” I tell him. When I’m around Ash I’m myself, I’m confident and I feel loved all of the time, but I still feel insecure with myself sometimes.

“My baby,” Ashton spoke softly “you’re so fucking pretty. So. Fucking. Pretty”.

Letting my arms go, he smiled at my actions and brought himself up and kissed me.

“These tits could make the Pope cum” he murmured, making me swat him softly and giggle. He pulled me onto my back and we kissed for a while, both naked and him on top of me. I’ve noticed that Ash wakes up with a boner and I could feel it between us, moving a little on my stomach as we kissed.

I felt one of his hands move down to between my legs, making me moan a little.

“So wet” he murmured, moving his fingers around my clit. I bucked up my hips, wanting to feel even more of him.

“In. Now” I said. Ash laughed and shook his head, kissing me hard again.

“You’re needy, and it’s cute, but I’m making sure you’re ready first.” I felt him slowly move a finger inside of me (I’m blushing so much writing this oh lord) and immediately move up to hitting g-spot. In seconds he made me into a gasping whimpering mess, making him groan and push another finger in. My hips snapped up and it felt so good that I tightened around him, looking down as he grazed his thumb over my clit.

I reached down and touched the head of him, making his breath faster.

“Ashton” I said slowly, my eyes going glassy. I could feel myself getting close. When he took his hand away I cried out, frustrated.

“I’m sorry baby” he said, kissing my forehead. “But I want your first cum to be on my cock” he whispered into my ear, biting it a little.

He pulled us over so that I was on top of him, looking down at (and I know this is cheesy don’t kill me) the man I love. I was sitting on top of his thing, and I started to move myself over it. I smiled when I saw Ashton’s reaction of closed eyes, but soon had the same when I realised that when it was pressed up against his stomach and I was on top of it, it could easily make my clit feel good. I could feel myself getting wet on him, the thought making me blush but I was so turned on I couldn’t care.

“Do you want to do it like this?” I opened my eyes and looked down at Ash, his chest flushed and hands on my hips, rolling me slowly on him.

“Will it feel bad?” I asked, realising what he was asking about. Would it hurt more? Would I do it right?

“Maybe for a second, but I’ll make you feel good quick I promise.” He said. “But only if you want to my baby”

“Okay” I said softly, moving my hands over his arms and chest. “How do I do it Ash?” He smiled softly and brought me down to kiss him before gripping tightly on my hips and moving them forward.

“Okay, I’m going to put myself here” he grunted, moving himself up until I could feel him brush against me. I tightened and nodded.
“And now you hold it, and make sure you feel comfortable” he said, watching me.

I felt the tip of him go in, and I winced. I wasn’t used to it yet, to be terribly honest, and it stung a little. I looked down at Ashton to see him flushing and his brows knitted together.

“Okay?” He asked.

“Mhm, just give me a minute” I replied, letting myself adjust to him. He was so patient, but when I felt a bit more comfortable I started moving down further. I still don’t really know how to describe how it feels to have sex, but I feel kind of empty and full at the same time. It’s kinda like a ‘holy shit, he’s inside of me’ moment. I lowered myself down until I was sitting semi-upright, my clit pressing on him and my legs on either side of him.

“You look so fucking delicious” Ashton groaned, making me giggle and squeeze around him.

“Don’t do that Tess” he groaned again, making me squeeze around him tightly once more.

“Fuck, do you want me to last?” He looked at me in the eyes and moaned. I smiled cheekily and sighed as he ran his big hands over my breasts and hips.

“Can I move?” I asked him.

“Please” he responded, breathing in sharply when I moved myself tentatively up and back down.

“Oh” I whimpered, feeling him in me and the sensation of my clit rub against him.

“Oh? That’s it?” He laughed

“Good oh” I replied, feeling too good to giggle along. Instead of going back up I rocked my hips and almost stopped breathing. I clenched around him, saying his name, before moving the same way again, circling and moving around. We alternated between me moving on him, me moving up and down and him moving from down below into me. Everything felt so good, so yummy. Ashton propped himself up on the headboard so we were almost facing one another, kissing me and encouraging me as I moved. When I say that I feel loved all of the time with him, it’s so true. Whenever I felt nervous and looked at him, he’d tell me things that made my heart melt.

“You make me feel so good” I told him breathlessly, blushing. Our rhythm had become both of us moving, his hand between my legs playing with my clit. I kissed down his neck, biting and sucking.

“Dare you to cum” I heard Ashton say, looking around at him to see him smirking.

“Oh you dare me that’s real mature Ash-“ I started but he started moving his finger harder, all of a sudden finding my g spot and making me bury my head in the crook of his neck and moan.

“Dare you to cum. Now. Cum for me” his words were whispered into my ear and that’s all it took. I clenched and squeezed around him, keeping my head buried in his neck and saying his name.

“Cum baby” I whispered, moaning, wanting to feel him let go (woah I’m cheesyyyy). Ash swore, moving faster and making my orgasm last longer and longer. Once he had finished and we kissed for a while I moved myself off of him, some of his orgasm falling onto my thigh and making him moan again. We took a shower together, made each other breakfast, and built a fort and watched movies all day and cuddles :)

So that’s that story! I apologise for not updating in a while, life’s been so busy but I promise I remember about GWS! Hopefully after next week I’ll be posting more regularly :) again, as always I’m not an erotic writer nor am I aiming to be one. I’m just writing because I like to do it and if you want to read more edited pieces there’s lots on here ?

Alllll my loooove, Tess (& Ash!!)

Source: reddit.com/r/gonewildstories/comments/b3p813/first_time_i_f_rode_my_boyfriend_m_tessa_update