What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What’s your current relationship status? Dating casually
What’s your sexual orientation? Heterosexual

Sleeping Alone

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Small prim and proper girl with cute perky breasts and a bright smile. We are in the same industry, knew each other for a long time as friends, and she got together last year with a guy who was also my friend. Let’s call her J.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I engaged J for a freelance job. It was an event at a small town a few hours drive from both my city and the city where she and her boyfriend lives. We both got separate rooms at the same hotel. I would be staying alone, J would be staying with her bf. She flew there, I drove and picked her up from the airport. Her Bf would take a later flight due to work. The event went well, jobs were done professionally and we got ourselves invited to an after-party. We were quite restrained, consuming just 2 or 3 glasses of wine and some snacks, then I decided it was time to leave and take J with me while we were still professional and sober. Never a good thing to let clients see anything else.

Only on the drive back to the hotel, did J turn her phone back on, and she got a text from boyfriend saying that his flight was delayed due to aircraft problems. As it was the last flight of the day, he was rescheduled for the next morning. As we all were leaving the next day, he was asking to take a refund instead. J seemed rather put out at that news. I asked if she was okay, J revealed she actually was afraid of being alone, she rarely travelled solo. I told her I could keep her company for a hour or so, or maybe she could call her bf until she fell asleep. She brightened a little at the last idea.

When we got to the hotel, we both checked in. As we were very late check ins, and I was a club member of the hotel group, the receptionist gave me a complimentary upgrade to a club suite, however I couldn’t wrangle the same for J who got the normal room we both paid for.

J said she would like to see my room before turning in, she had never seen a club suite from this hotel group. So we went up to my room first. It did not disappoint, with a good view of the river, a sofa bed and king bed, a large open bathroom with a huge tub. The nicest was a miniature bottle of red and a fruit basket on the desk. I invited J to share it, she said sure, but maybe after a shower.

She went back to her room and I ran hot water for my bath, and then my room phone rang. It was J. She asked if there was hot water in my room and if so could she use my bath, her shower wasn’t hot enough even at maximum. I said yes, but surely she should call to complain. J said it was too late at night and she could not be bothered to wait for repairs or a room change.

J seemed to have forgotten that my bathroom was open when she came back in. She stared for a moment, and I offered to step outside to the gym or lobby (and then I could complain!) while she bathed. With a wry smile she said never mind, I am already bothering you so much, and I trust you. She went in.

I switched on the TV which was thankfully facing away from the bathroom. It had been a long day and long drive to the town, I dozed off. I was awakened by a moist hand on my shoulder. J shyly shook me awake.” Hey, sorry I’m done. You must be really tired, I’m going to go back, sorry for disturbing.” My eyes took in the heavenly image of her in a tank top and hot shorts, with steam coming out of her wet hair. “Uhh don’t go, help me finish those fruits and wine. I’ll take a quick shower and join you.”

I ignored the steaming bathtub and went to the standing shower and did a quick scrub. I am trained to be very fast and can totally refresh myself in a shower in 2 or 3 minutes. I put on a bathrobe and stepped back out.

J was already started on the fruits, I opened the wine and poured it out. We started talking about the days work. The wine was soon finished and I took out a small bottle of Chivas and another of Grey Goose and we finished that too quite quickly.

I noticed J was stalling and kept the conversation going even though she was obviously tipsy, was she really afraid of being alone? I told her bluntly she could have the bed, I didn’t mind the sofa bed if she was scared of sleeping alone. A part of me was happy to have eye candy for the night. J blushed and said softly that she felt like a coward but she really had not been looking forward to sleeping alone. Curiously I asked if she slept in the same room as her bf every night as I knew they both rented different rooms. J floored me with her blunt answer, saying that her bf and her fucked almost every night and yes they always slept in the same room. I awkwardly laughed and said oops, no action tonight thanks to the airline.

I had no real idea what happened next and according to J neither did she. We both giggled and look each other in the eye. And suddenly we both understood we wanted it. We were in an embrace. Our lips met.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I gently carried J to the bed and laid her down. I asked her if she was ok with where we were going. I honestly felt a little surreal as J had always seemed so prim and proper. J just smiled shyly and held me closer.

Ungodly thoughts rushed through my brain, most of all the guilty knowledge that J’s bf was my friend too. But I succumbed to the dark side. I unbuttoned and unzipped her shorts, while she stroked me through my shorts. I them rolled off her top, exposing her tits. I covered her body in licks and kisses prompting some giggles as she kept stroking me to my full girth.

I took off my own clothes and whispered in her ear, do you do blowjobs? J breathed no sorry. I was rather disappointed as I love them. Brushing aside lewd images of her mouth, I put my hand down to find her soaking wet already. I stared at her incredulously while she shyly hid her face in her hands. I gently pried them away and kissed her and positioned myself above her for entry. As I slid into her, she gasped. I slowed my pace and asked curiosly, am I large? I don’t think I’m as large as your bf. She giggled, how would you know? Just my guess, I said. She did not reply me but guided me in a little deeper with sigh of pleasure. After a few strokes, I remembered my condoms and went to roll one on.

We made love like this for a long time. I tried to change her to doggy or cowgirl but she refused saying she only liked to be on her back. After about 20 minutes of love making, her phone buzzed. I looked over at the table.Crap it was her bf. J could read his name on my face. And anyway who else would call in the dead of night. J shook her head and told me to continue. Her phone buzzed again, it was some texts. I slid out of her, exiting with a slight pop and a sigh from J that expressed both passion and guilt.

I gave her the phone and we both read the message “Hey babe guess you’re asleep? He must have worked you hard today. I wish I was with you to help you to sleep. And good news, I was given a raise today, I checked with the banker and he says it’s just enough to secure the mortgage on the place we wanted! Wake up happy to this baby!” What a sweet message.

I stared at J, you guys are getting a place? It sounds very serious. J seemed overwhelmed by guilt as she stared at the ceiling. Then she suddenly said in a husky voice unlike her normal self, yes we are probably going to be engaged soon. The devil in me awoke at that point. I kissed her and took the phone away from her, turned off the notifications and threw it on the floor. All justification I had on the edge of my lips to advise her to continue with our night was lost as she in turn embraced me.

I removed the cap and proceeded to fuck her raw and with more abandon and vigor. In return J became more vocal, and more urgent. Her hips moved to meet mine as we danced the dance of boy and girl. In my mind every thrust I was punishing J for her betrayal of my friend, while enjoying in a perverse way that I was the craven man who was enjoying her forbidden love canal. J began biting me on the right shoulder as we intensified. I eagerly bit her back on both her left neck and breast. I was about to cum. I pressed as close as I could and loosed my baby batter into her. She tensed up as she felt it, the liquid of a man who was not hers.

We sat up and talked after that. Strangely it was about the life she wanted to have with her bf in the future. At no point did we discuss what we were doing. I broke that by bluntly asking if she had ever given a blowjob in her life. J said she tried twice but she found it really disgusting. I turned her on her stomach and forced myself at her mouth.

J was totally shocked. She was frozen for some moments then began gagging and pushing me away. But somehow I felt that she would not deny this to me. I held her face and began thrusting. She scratched my thighs in an effort to loose herself but I had a death grip on her hair and continued to face fuck her. Tears ran down her eyes and saliva drooled out of her mouth as I went in and out. The excitement was a good trigger and I released another wave of sperm into her, this time in her mouth, which according to her had never received such treatment.

She cried for a bit and I let her, before going close and kissing her again. She let me, before quietly asking, why? I said, I dont know. This is all crazy. This whole night is crazy. Im fucking an old friend, who is probably going to be married to another old friend. I feel like I’m in a dream and I might as well live all my fantasies. You have fantasies of me giving you a blowjob? J asked quietly. I stuttered. Yes i finally said. J didn’t not give a reaction for a while. Then suddenly, she pushed me down and looked me in the eye. Whatever happens tonight stays in tonight. Never speak of it again. We crossed so many lines, I don’t want to see another line tonight. With that she took me into her mouth. She actually tried to suck me off but it was obvious she was not enjoying it and not very good at it either. I soon grew aroused again though and I went to her favourite position again.

As we fucked, I told her, please forgive me for anything tonight. She replied, nothing needs forgiving, but never speak of it to anyone else. And with that, we did not speak a word for the rest of the night, just fucking ourselves into exhausted oblivion….

I woke up to soft sunlight on my face. I dimly wondered why the night was so peaceful. Of course! I had not switched my phone on since yesterday. And I had such good sex! As the light made its way towards her face, J slowly began to stir, I switched it on. While waiting for it to boot, I could not resist, and began lightly fingering her. She made some pretence of wrapping herself like a burrito in the sheets and squealed when I lifted them off but wrapped her arms around me and enthusiastically welcomed my erection into her moist tunnel. With the rays of morning light bringing a surreal sheen to our sweaty bodies, we fucked and fucked in missionary. Our arms were around each other squeezing hard, our bodies making embarrassingly squelchy sounds as perspiration rolled down our skin. As she cried out over and over again in agonising passion and clung to me, I let out primal grunts too and poured every last drop of my manhood, every last ounce of my energy, and every last thought of my lust into her. We collapsed on each other, not even able to differentiate between each others bodies, such was the link we had accomplished in the last few hours.

I rallied myself to check my phone when I heard a buzz. The first thing I noticed on the screen was not the mundane numbers of AM and PM however, but the notification of 2 texts from J’s bf.

The first at 3.23am read, “Hey they refused to give a refund so im on a plane after all. Im cmg soon, be thr by 7am! Help me wake J plz she mus b asleep, not replying. U must have worked her hard, haha!”

The 2nd text at 7.45am read, “Hey man J’s not answering me. R u awake? Which is her room? I’m almost here.”

A last text at 7.52am read, “Man, J’s not answering her room phone according to the receptionist and her hp is off! Im worried whr is she, get up please! Ur room phone isnt working!”

I hurriedly checked. The current time was 7.55am. Before I could shock myself into action, there was a soft but firm knocking on my door. Bleary-eyed, me and J stared at each other and at the door.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? There was a mad rush for J to clean herself up and act as if she had just woken up, whereas I had to hide the used cap, wrapper and the box, and make it look like I spend the night on the sofa. Then we could open the door and welcome in, yes you guessed it, J’s bf and a bemused hotel bellboy. I gave him a good tip for his trouble and he disappeared at my wink.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, Power / Dominance, Didn’t want to disappoint my partner, Revenge / Getting even, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody. It would be terrible to J.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I have to carry the guilt around J and her now husband every time I meet them. And the worst thing is I can’t help but feel that both me and J want it to happen again but know that it is very morally wrong.

What was the BEST thing about this hookup? Amazing sex.

What was the WORST thing about this hookup? Forbidden sex.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

You have a hookup story to share? Submit it here!