Sex IRL: The massage therapist who doesn’t get her happy ending


sex IRL  • 

Sex IRL: The massage therapist who doesn’t get her happy ending

‘He can tell I’m nervous as I haven’t had a dick this big for ages’

Sex IRL is a series by babe dedicated to detailing the ups, downs and in-betweens of real girls’ sex lives. It’s unfiltered, graphic and, most importantly, real. This week, a 26-year-old massage therapist who fucks an older man she met on Tinder. 26, bisexual, Caymen Islands.

Day 1

8 a.m. Wednesday morning. I wake up and aimlessly scroll through Snapchat, Instagram and then Tinder. Living on a tiny island, my options are very limited so I reach my limit on Tinder on a daily basis.

8:10 a.m. A new man pops up for a change, he's older. I'm pleasantly surprised. It's normally horny tourists and couples looking for a threesome, because being bisexual seems to be code for “GIVE ME ALL THE THREESOMES.”

I can't really see older man's face in his pictures but I think he's hot. We matched! He instantly sends me a message about my bio. It always reads "a great rack and an open mind" which is a quote from a UK TV show. It’s always a good ice breaker, since when has a great rack and an open mind not been a man's type? He says he "love the honesty and humor" and we start chatting.

2 p.m. We swap numbers and start talking about our lives over text. I'm sat at my boss’s house drinking tea and playing with her dog. He lives on the beach and has a big beard. We'll call him Castaway. He starts talking about rock climbing and asks what I do for work. I'm a massage therapist, which generally gets a “how much do you charge for happy endings?!” response. He tells me he thinks I'm gorgeous and that I look like lots of fun. Pretty sweet to hear.

5 p.m. I'm moving house tonight. I'm laying on my new bed and he's messaging me pictures of his face. He's 18 years older than me, tall and fucking gorgeous. He tells me "I can be a true gent or an ass slapping dirty talking daddy dom." I'm sold. I message back asking when we're going to meet.

Day 2

9 a.m. We had organized to go for a drink tonight but Castaway says he's now got work and needs to take a rain check. I was pretty excited at the prospect of having sex tonight but I guess I'll spend my evening with myself.

6 p.m. He says he can still meet for a g&t when he's finished. I’m about to go into work to see my last client of the day at a hotel in town. I tell Castaway I'll meet him later.

8 p.m. Finished my client, spent the entire two hours thinking about how I hope I get some tonight.

8:15 p.m. I stop at the shop and buy a slice of pizza and condoms. Gotta have some energy and line my stomach, although maybe condoms might be wishful thinking? I used to think taking condoms on a first date was “slutty” — now I realize there is no such thing as slutty, and as a girl who loses her mind on any kind of hormonal contraception and has a mild latex allergy, it's definitely better to be prepared.

8:30 p.m. I put makeup on in my car mirror, in the dark, on top of dehydrated, sun frazzled skin. I also try to have a wet wipe shower and I change out of my uniform into some shorts and a low cut vest.

9 p.m. I’m at a beach bar having a g&t and Castaway texts to say he's just pulling in. He looks good, despite wearing his work clothes and having spent the last few hours sailing. I'm feeling really comfortable and we chat and laugh. He does most of the talking, but I'm naturally a listener. He tells me about when he was back in London and doing loads of coke, I'm not entirely sure how to respond to that if I'm honest.

I get up to go to the toilet and I'm wearing my sexiest shorts. High waisted, super tight, super short. I always get complimented on my butt. I have the kind that jiggles when I walk. I can feel him staring. I come back from the bathroom and he is still standing up at the bar, I wonder why he doesn't sit down? Conversation turns to sex and I realize that there are some people I know sitting nearby, I hope they don't recognize me. He asks me what my biggest fantasy is, but I feel too shy to tell him. We have only met less than an hour ago, and not everyone is up for open discussions on pegging, being choked and cum sharing on the first date. I mention that I like girls. He seems surprised. I have to reiterate that I also like men. Being bisexual isn't a transition period and it is a real thing.

10 p.m. Things get hot and suddenly he's whispering what he wants to do to me in my ear. He tells me he'd love to slide up behind me as I stand at the bar, push my knickers to the side and fuck me in public. I've had two very strong g&ts. I admire his confidence. I realize as I'm sat down he's stood up and his dick is not only hard but also huge and pressing against my leg. I teasingly brush my hand over to see if he's as big as he looks. I can't wait to see it.

10:10 p.m. We go and lay on a sun lounger on the beach and he turns me over and starts massaging my ass. He's an ass man for sure. His dick gets hard and he pulls it out of his shorts, he leans over me and we kiss. He asks me if I like his cock and I move my hand back to gently stroke it. He asks me if there's anything I'd really like him to do to me and I tell him I want to be his good girl tonight. I love being called a good girl and being told what to do.

10:30 p.m. I'm laying face down and he's behind me, we're kissing and I have my hand around the back of his head. He's such a good kisser, I can feel myself getting really wet.

10:50 p.m. He tells me he'd love to feel himself push his dick into my juicy pussy, I can't wait any longer and I ask him how far away he lives from here. He says 10 minutes.

11 p.m. We're driving back to his. He's in his car and while I'm following behind in mine. He calls me and tells me to take off my bra. As an extra surprise, I take off my panties for him too.

11:10 p.m. We're in his flat, he moves fast. He's much taller than me and stands behind me and unbuttons my shorts, he slides them off and bends me over the kitchen surface. I'm stood with just my top on and his soft hands move over my belly down to my pussy, I'm soaking wet. He moans “Yes baby, good girl. Are you nice and wet for me?” as he puts his fingers inside me then into his mouth.

11:15 p.m. He says he hasn't had a chance to shower yet. I decide to get in with him and he soaps me up. He's stood behind me lathering up soap over my tits.

12:30 a.m. We're lying on his bed and he's been down on me for nearly an hour. This is amazing. He rubs my clit softly with his tongue and sucks his finger and then slides it into my ass. He orders me to move and tells me he wants me to fuck his face. I straddle his face and grab his hair to move his head backwards and forwards. He tells me that I taste amazing. I'm almost scared of having sex with him because his dick is so big, we decide we're having fun anyway.

2 a.m. We didn't have sex but have fun doing everything else. We fall asleep.

Day 3

6 a.m. He wakes me up by going down on me. He really knows what he is doing. He eats my pussy like he's hungry, licking gently over my clit and then sinking his tongue in. He puts on a condom and fucks me. He can tell I'm nervous as I haven't had a dick this big for ages, so he slides in slowly, filling me up. His body is big and muscly and I love the feeling of his big shoulder being rammed into my face as he fucks me. I dig my nails into his ass as he gets faster and deeper and I come hard. I take the condom off with my mouth, sucking his big hard dick, spitting on it and sucking him until he fills my mouth with his cum.

7 a.m. He has to leave for work. He picks me up and I wrap my legs around his body, we kiss and then I leave. I look exactly how I feel – fucked.

2 p.m. I get a message while I'm with a client. I look over and see it’s Castaway. He says he misses the taste of my juicy holes and that we should do it again sometime. I agree and we arrange to meet at the cinema tomorrow. I'm pretty sure that's code for let's fuck in public but I'm down with that.

7 p.m. Castaway texts me to say he loved waking up with me in his arms this morning. Awe. He seems pretty genuine, I've met a lot of assholes and can generally get a sense of who's real. It's quite nice to feel wanted.

Day 4

8 a.m. I text him a picture of me in a top that shows my cleavage. He approves. Calls me kitten. I like it.

6:30 p.m. Just finished with my client and I head over to his place. He's smoking on the beach. We sit and chat for a while. He again does most of the talking, mostly about himself. I get the feeling he is a bit of a know-it-all. But a nice guy all the same. He looks even hotter than before.

7:30 p.m. We decide against the cinema, we're both pretty happy staying in together. We plan to go and buy some gin but don't make it that far. We're back in his flat and sit on the sofa. We're kissing and he takes off my top. I'm not wearing a bra, he starts pulling hard on my nipples. He turns me over and he's burying his face in my ass. He orders me to get onto all fours, he licks away at my ass and reaches around to rub my clit. It's almost as if he knows my body better than I do. He's obviously very experienced and it's pretty exciting.

8 p.m. He is really dominant and I'm so turned on. I love the feeling of him being so big and me being helpless below him. He gets me to call him 'sir' and spanks my ass hard when I don't. He asks me if I love his cock, if I don't say 'yes sir' he spanks me, harder if I say it quieter. So hot.

9 p.m. He has loads of toys. First of all he gets out a dildo and fucks me with it, he loves watching the big dildo go in and out of me. I'm laying on my back on his bed. He gets a whip out, orders me to sit up and hold my hands behind my back. He hits my tits with the whip, my skin starts to go red, it stings and makes me gasp but afterwards I feel so warm, I feel myself getting soaking wet.

10 p.m. I'm getting tired so we put a film on. It's not as interesting as sex with him…

10:10 p.m. The film doesn’t last long as I start sucking his dick. It’s way more fun. I'll sleep when I'm dead.

11 p.m. We eventually fall asleep, him on his back and me cuddling up to him with my head on his chest.

Day 5

6 a.m. We wake up and fuck. He checks that I know the color codes if it gets too much, I say yes, and then puts his big hands around my throat as he continues fucking me. I come.

11 a.m. We've been fucking for hours. He's got a big mirrored wardrobe and I love watching his perfect body on top of mine in the mirror, his muscly back and watching him thrust in and out of me.

12 p.m. I've come three times already. I have a huge hand print on my ass from all the spanking and a mark around my neck from being choked.

12:20 p.m. He makes me breakfast and coffee and we talk. He talks about all the different places he's lived – from my experience of traveling around there are a lot of men who I refer to as “travel wankers” – men who have been everywhere, seen everything, can tell you the best island in Thailand, blah blah. It dawns on me that he likes the sound of his own voice and I'm pretty sure he thinks he's more interesting than anyone else.

1 p.m. He goes down on me for the 100th time. He tells me he'd love to eat my pussy all day but has stuff to do. I shower and drive to the pharmacy. Bought a gatorade and the morning after pill. Was an idiot. Got caught up in the moment and didn't use a condom.

3 p.m. It's really stormy on the island and I get home and watch the storm from my bedroom. I text him and let him know I've taken emergency contraception. He replies with “good idea, thank you.” He initially agreed to pay half for it.

Day 6

2 p.m. I'm just finishing my client and driving home when Castaway calls me. Tells me he's bought a butt plug. He seems keen to see me again. I'd love to see him again although I'm a little worried about catching feelings. I text my bff for advice and she tells me it would be a better idea to see him less often.

6 p.m. I get a text from a guy I slept with a while ago, although he’s hung he's quite intense. Maybe two at a time sounds messy. Maybe I won't reply, he's a bit too full on so I ignore the message. I think I'm starting to feel depressed because of the hormones from morning after pill. I have some wine.

Day 7

8 a.m. Text Castaway a picture of me lying naked on my bed with the caption "morning."

10 a.m. I see the blue ticks that show he's seen it. No response.

9 p.m. Still no response.