A Few Firsts

I took me a long time to forgive myself for what I'd done. I thought what I did was unforgivable, cruel even. However, with almost fifteen years of hindsight, I think inevitable would have been the better word. Let me explain.

An 18-year old me, (Eoghan, pronounced "oh in"!), fresh out of school and weeks before starting college (Maynooth University, here in Ireland), had kissed what was one of my better friends at our debs. (Think end of year graduation party). The stress of having a date for the debs was very real, and to cope, most of us slightly awkward guys and girls had just asked friends to go strictly as friends. Melissa was the date of one of my best buddies. I knew Melissa very well, summer job together highlighting the time we spent together in class as well, great fun, good looking girl. Never one I had looked at as someone to try "score" as it were. A part of that was probably her obsession with Tom, the above named buddy who accepted Melissa's proposal to be her date. Now, Melissa made it no secret that if Tom were to attempt anything at all with her she would be very willing to proceed. Unfortunately for Melissa, I knew Tom had zero intentions with her and assumed that would stay the case. This is all very high-school drama stuff I get it, but just bear it in mind for now.

Debs night came, drinks were had, tears were cried, Tom hooked up with Elaine and Melissa ended up sobbing into my shoulder because I'm the sap that would listen. Again, very high school drama nonsense. If you knew me personally, you would know where this ends up straight away, so a brief synopsis, I felt bad for her, we kissed, awkward few days afterwards, and long story short we ended up going steady. She was going to a different college, but still only in Dublin so just up the road. I started university a with a one month girlfriend who was obsessed with my friend, (who I was in college with, I might add).

A quick zoom out if you don't mind. I was obsessed with Gaelic football in school, didn't care about anything else, wanted to play for Dublin, was on the development teams growing up etc. So I hardly ever drank, I almost never went out. Never really got up to any major mischief. Had a few girlfriends, but they were never the sort who would go any further than kissing and maybe second or third base. I was a good looking lad, had plenty of interest, but never any "action".

I started university in the same boat. Apparently, Melissa was the take it slow kind of girl. Now, I do need to stress, if I could go back in time and put an arm around my younger self's shoulder and give some advice, I'd tell me to cop the fuck on and break up with her. A professional might give a different analysis, but I suspect to this day that my competitive nature just couldn't sit with the fact that I knew If Tom came in and asked the question, Melissa would want him instead. I had to beat him. I had to be the one she wanted more than him. Insane I know, especially when I hadn't wanted her in the first place!!

But look, mistakes happen, people cop on and make the right decisions and things generally work out the way they are supposed to. Right? Well, I graduated from university 4 years later with a degree, a higher diploma in education and a fully intact virginity card. Those were my college years. Gone. The only thing I had learned about sex and general sexual exploration is that it's something that's given to the very very lucky. It's for others. It's still difficult to not be embarrassed by that fact, but there we were. Still going out 4+ years later. Sexless, with loads of excuses, and she was looking at houses that we should get. I was often praying in the staff room that I wouldn't get pulled into a conversation with other teachers about sex in case I said something that "outed" me. It was mortifying.

So what did I do that was so cruel and unforgivable? Dan, (a thirty something year old PE teacher) was getting married. A few of the lads from the staff room, myself included were invited on the stag. It was my first invite to a stag, and with none of MY friends there, I'll admit I was slightly outside of my comfort zone, but the lads were unbelievably sound and I was sure it would be good craic. We weren't exactly going to Las Vegas now, but a day out drinking in the local town that he grew up in, Mullingar, went by in a flash. A pint or two in every other pub on the main street meant that by about 1.30am we were in the queue for the nightclub with about half of the lads still standing and the other half god knows where! I had spent most of the night just trying to keep up with the lads, so much so that I had barely noticed Sarah, her sister and a few other local Mullingar girls nearby. (I would love to tell you Sarah's real name, we definitely exchanged names but your guess is as good as mine I'm embarrassed to say).

We started having the craic with Sarah and her sister as a group at first, and then it became apparent, even to very drunk me that Sarah had her eyes on me. Now I wasn't exactly behaving like Casanova here, but I'd obviously said enough to hold her interest. Decision time came when sister started pulling at Sarah's hand to get her going home. I'll never forget these words, drunken me remembers this night patchily, but this line vividly. "No you go ahead, I'm going home with Eoin, yea?". Eyes locked on mine for every word. Zero chance of misinterpretation. I glanced around at the leftovers of our bunch. We were all over the place. I could slip away and nobody would know. "I'll get her home yeah, no hassle". Decision made. As I locked arms with Sarah and gave one last look over my shoulder to double check my "getaway", my heart was thumping in my chest. Hopefully nobody had noticed me slinking away.

A taxi rank was found fast enough, Sarah was in her home town so guided me straight there. Even in the short queue for a taxi, I was simultaneously inventing elaborate excuses for the lads for why I had left early (as if they'd even notice) and also making poor attempts at convincing myself that I could just drop her to her door, tell her I had a girlfriend and that I couldn't do this to her. I couldn't do this. It was wrong. We were in the taxi. It was still wrong. All of those thoughts started to drift away when she leaned in and kissed me while squeezing the inside of my thigh and letting her hand nudge up against my rapidly growing dick. My instinctive, chimpanzee brain took over. This was fine. I don't care anymore if I'm cheating, I wanted this right now. Her already short dress soon had my right hand brushing over her lace panties and making her gasp into my mouth as we kissed.

This gave me my first feeling of taking control in the whole situation. There was a lot of new stuff happening for me right here, but I swear if there was an international competition for hand use, I would medal. I was completely in my wheelhouse. After all, it was the height of sexual activity I had had! I knew I was good here. I can still feel that sensation of how wet she was instantly when my fingers found that slight protruding mound running down the center of what were some very sheer and lacy panties. The taxi ride was all too short, but was probably for the best as I needed to feel some skin on my now rock hard dick.

Twenty euro was hastily thrown to the taxi man and we walked up to Sarah's house. Sarah had a house. I hadn't even asked. I was still in my early 20's, I still lived in the world of shared houses. I inquisitively asked if we needed to be quiet. "No, all good. My son is at his dad's for the weekend". This was said as casually as if she had told me her family situation already. Which, to be fair, she probably had. "Ah right, that's cool". How old was Sarah? She had kids. Well she's done this before then, that makes one of us. My anxiety tripled. Did I need to worry about who was in here? Was this all an elaborate prank with me as the joke? Sarah was 28. She had told me as we all guessed each other's ages. Relax Eoin. I reasoned with myself. Just go with it.

It didn't make sense to me that she actually just wanted to sleep with me. Perfect hindsight again here, she just wanted to fuck and let the rest was just be the rest. But I had developed such a warped idea of what sex was and could be that I had no clue that it could be like this. Of course, I wasn't thinking about any of this then, I was just thinking if I was about to make a huge mistake.

"Are you okay?"

The question snapped me back to reality. "Still fancy that cup of tea?". The slight grin told me that there was to be no tea. "Yea, yea of course. Sorry, I thought I left my wallet in the taxi, but I have it here, all good". Monkey-brain kicks in again. Especially as she opens her door with one hand pushing it open, and pulled me in by my belt with her free hand. The door is closed, and I'm in her house. The newest of new territory, but my rock hard dick was doing the thinking now.

In what looked like a practiced move, she kicked off her heels and dropped till her eyes were level with my mouth, rolled her shoulder back and dropped and caught her jacket behind her before it hit the floor. She was absolutely stunning in that moment. Maybe 5'4, jet black hair, she looked athletic without looking thin. She had thin lips which leant to her mischievous smile, a genuinely really attractive girl. Her eyes were a deep green, another glimpse of the night which remains incredibly vivid.

I shut my jaw quickly enough to stop her thinking she had brought home someone who'd just escaped the mental institute.

She seemed to operate at a much slower pace now that she was home. The urgency was still there, but now she seemed more inclined to take her time. She approached me again with a lustful look in her eyes as she started to unbutton my shirt. Just the top three or four buttons, then she ran her fingers under my shirt and over my chest, pausing just to the sides as she leaned up on her toes and kissed me again. I knew what to do here. Finding the zip on the back of her dress, I used my free hands to slowly slide it down. She arched her shoulders and her lower back to allow my hands reveal her very impressive body. The top half of her dress was now down and acting like a skirt, her lightly tanned skin offset the white bra which was doing an excellent job framing some very attentive b or c sized breasts.

Her dress stopped at her waist as she turned and lead me by the hand to her bedroom upstairs. I was in absolute ecstasy. Melissa, and any sense of wrongdoing was now a million miles from my head. The smell of her perfume was intoxicating. She closed the door behind us, and offered me to "make myself comfortable" on the bed while she went in to her bathroom.

In for a penny, in for a pound. I did rationalise that I had already done something wrong, and that now I might as well follow through and see where it takes me. As I did that I also debated with myself whether to take off my underwear or leave it on, or get under the covers or not. This was all very new to me remember. I barely had time to decide. As my jeans hit the floor, Sarah reemerged in just the white bra and bright yellow, lacy panties on that my finger tips were getting acquainted with earlier. She gave a throaty moan as she eyed me up and pushed me back on to the bed, the lust in her eyes letting me know that she was as in to this as I was. Her enthusiasm encouraged mine as I whispered hot she looked and caressed her sides.

Another new experience for me, Melissa wasn't heavy by any stretch, but she certainly wasn't athletic. Chubby was probably the word. Sarah felt so slight in my hands, and her skin was so soft. She was standing at the foot of her bed while I sat up feeling her body. My hand slipped up her back and released her perfectly proportioned tits from her bra. Each nipple quickly found my mouth as I pulled her into me. Her slight gasps as I flicked my tongue over each nipple making them harder just sent more and more blood to my now throbbing cock. I needed to feel her hands on me.

She leaned forward on to me and pushed me on to my back once more. I watched with hungry eyes as she slid her panties down on to the floor revealing a neatly trimmed dark bush just above an incredibly tempting pussy. As I was soaking in this view, she slowly grabbed my boxers by each side and with a grin began to ease them down my legs as I gratefully lifted my hips to allow. She purposefully let the top of my cock catch on the way down and then pop out as she went too far. Her eyes were now focused entirely on my cock.

Kicking off the boxers to now leave myself laying on the bed, she climbed up, legs on either side of my waist. Again, feeling like she was taking her time, she slowly leaned forward again, letting her dark hair fall down over my chest as she brought her face up to meet mine for another passionate kiss. I could feel the wetness from her pussy as she rubbed herself along the length of my 7 inches. She groaned and shivered as she moved. "Fuck, you're so hard". I was.

My hands were on her thighs as I encouraged every move forward and back along the length of my dick. I don't think I'd ever been as hard in my life. "There's condoms in the drawer". With a brief moment of eye contact she nodded towards a bedside locker. I was relieved as I didn't have any and I really didn't want this to end because I had given up buying condoms! If I'm being honest with myself, I would have gone with it anyway, and I think she'd have done the same. I leaned back and grabbed blindly into the drawer and pulled out the first box I could. Jackpot.

Without hesitation, she took them, opened one with her teeth and in one very impressive motion, sat up and with one hand behind her back grabbed my member and slid the condom on without fuss. She raised me up and pointed me at her pussy and slowly began to slide down onto me.

Within three or four motions, I was balls deep inside of her. Absolute magic. At first she didn't move, just stayed still and groaned like she had been waiting a while for this moment for more than a while. She certainly wasn't waiting as long as I was! I could feel her pussy contracting and throbbing around me as she lay relatively still. Every muscle in my body wanted to start her bouncing up and down on me. Sure enough, slowly at first, she started to move up and down on my dick. An inch or two at first, but once we were both comfortable with how we were moving she started to pick up pace and larger strokes. She was up on her knees now with her hands on my chest while I began to resist the urge to blow my load immediately. Jesus Eoin, don't come straight away.

Leaning down again, she put her arms around my neck and began grinding her hips into mine. She was much faster now, and I could feel every inch of her pussy. I would love to tell a tale of a 3 hour session but I was brought to the brink extremely quickly once Sarah changed position. I tried to slow her down by grabbing her hips, whispering "wait" into her ears but this just made her speed up. She grinned as she made me violently come, moaning "FUUUUUUCK" as I did. Her sly grin told me she enjoyed that. As she carried on the same motion, I soon became overwhelmed with the sensation and had to get her to stop.

Being the man that I am, I NEEDED to make her come too, and my dick was out of order for the moment. Hard but too sensitive for anything useful. I flipped her over onto the bed and lay down beside her and slid two fingers into her pussy, filling up the void left by my cock. She quickly showed her approval by bucking into me further. Turning my fingers up, a sudden gasp let me know I'd found her G spot, I angled my hand so my thumb was also rubbing her clit on each stroke. I quickly got into a rhythm that matched her swiveling hips, and before long her arms were up over my neck pulling herself down into me. Moving from kissing her neck to flicking her nipple with my tongue put her over the edge and she shuddered to an orgasm on my hand. I had made Melissa come countless times with my hands, but this was different. This had an intensity that I had not experienced. There was a depth to it that was new.

Once we had gathered ourselves again, we climbed under the covers and with one dim beside light on talked as if we were getting to know one another. The animalistic part of the night was over and now a much more familiar part for me was coming in. We talked about each other while our hands were slowly exploring each other for another twenty minutes or so when they began to wander again. First hers to my cock, rock hard again, and then quickly mine following her lead to find her warm pussy once more.

Sarah turned her back to me and guided my dick to her pussy again from behind without a word being spoken. This time it was me who grabbed the condom and popped it on as I slid easily into her. My hands caressed her tits while we lay on our sides and I slowly pushed into her. There was less gasping and more deep moaning this time, there was no rush to release, no eagerness to finish. We were both biding our time as I slipped in and out slowly. I can still hear the sound of her pussy as we breathed and moved together. The smell of her hair as I kissed her neck and stroked her tits softly. Sarah didn't give much away this time, which helped me keep it together if I'm honest. But she was suddenly cumming again and this time on my dick with me slowly sliding in and out feeling her grip my cock. The throbbing of her pussy pushed me over the edge again as I came deep inside her while pulling her ass back into mine.

We stayed like that until sleep took us both.

I woke up the next morning to an existential dread, running all of the scenarios through my head of being caught. What if she's pregnant? What if she knows Melissa? What if one of the lads tell her I disappeared with a girl that night? What if? What if? What if?

I left Sarah in bed early that morning, she acknowledged my leaving but didn't seem too bothered, we had exchanged numbers after all. A taxi to the rented house with the other lads from the stag, and straight into my car for the drive home. I promised myself that this was a once off deal. I didn't want to be that guy. I deleted Sarah's number and spent the next few weeks panicking at calls from private numbers, all false alarms. Seems Sarah got exactly what she wanted out of it after all. In times of fights with Melissa, typically over our non existent sex life, I would often fantasize and wank off about that night with Sarah. A very real fantasy of someone who actually WANTED to have sex as well. I shouldn't have considered it a fantasy, as my exploits would show over the next few years. I'll get into that journey in coming stories.

Granted, it's a slightly pathetic beginning to my own sexual journey, spending four years with someone and never proceeding past a hand job, to my first time fucking being with a woman I had known for perhaps two hours. My first time cheating. Not a badge of honour for me, but also not the last time that for that either I'm embarrassed to say. At least I wouldn't be a virgin at the age of 23.