My First Time - Halls of Residence

My name is Craig; I am nineteen years old, at least I will be next month, from just outside Stornoway on the Isle of Lewis on the west coast of Scotland; this is my story.

Currently I am studying at two Universities in Ayr and Glasgow; my career plan is to work on cruise ships as a Purser. To do this I need business administration and maritime qualifications, hence the split locations.

I am five foot seven, with short brown hair, slightly overweight too; but working on losing some weight. However I look stunning in my Naval Cadet uniform, which I have to wear on certain occasions. I don't have any girlfriend as such, still a bit shy and reserved on that front; but working on that too.

The Halls of Residence that I was to have been living in, near the centre of Ayr had a major flooding following a water pipe bursting in the roof. We were all decanted to various local B&B's until repairs were carried out.

I now have a room with a single bed, small wardrobe, an upright chair, which doubled as my bedside table and a small table for writing on; to do this I have to sit on the end of my bed. No cooking facilities, special provisions are made in the University for us to get meals there. On the plus side we do not have to pay for it; as a student every saving helps.

On a Friday I have three lectures at the Maritime College in Glasgow; which entailed me getting a one hour train or bus ride up there. As there is more to do in Glasgow than Ayr I like to stay on and get a late bus or train back.

I overheard three girls talking at the college one day that they were all going to the 'Underground' club tonight; thought I would give it a try. Found it on the internet, not far from the college. As I had an assignment to complete I worked on in the college library, finished it and handed it in.

I arrived at the 'Underground' about seven thirty, still quite but was starting to show signs of getting busy. I got my usual pint of beer that I could stretch out, found a free booth, sat down and waited to see how things developed.

Nothing was happening, I must have arrived there too early, and not sure what to do, slowly nursed my pint of beer, daydreaming, cannot remember about what. A very polite voice woke me out of my dream; asking if the seat opposite me was free. I said yes; he sat down; was taller than me and dressed in a smart business suit, complete with brief case and umbrella. Don't know what his age was, early forties maybe, blue eyes, light brown going on fair coloured hair. Had a large whisky, something I missed, not having access to my father's supply and being a student.

He introduced himself as Malcolm; I introduced myself, and we exchanged handshakes. Both being alone we started chatting, he worked in Glasgow and was held back sorting out some client problem. I explained about my University arrangements and finishing off an assignment. Some of my college students mentioned here and I thought I would give it a try.

We chatted for well over an hour exchanging details of who we were and where we lived. Turned out he lived in Ayr too, in an apartment block near the Fairfield hotel which I knew; I commented a very nice area. I explained about my trials and tribulations with my Halls of Residence accommodation. He said that Ayr has been suffering quite a bit with old, badly maintained properties, causing major problems in the town.

He offered to buy me a drink; I gave a courteous decline. He said he remembered his poverty days as a student. I said ok as one does. He came back with two large whiskies, no ice, no water, and said I trust that an islander enjoys whisky this way; this one is distilled on Arran. First time I had tried that malt; it was very good. We chatted for about another hour or so. Malcolm said; as nothing was happening here do you want to head back to Ayr with me and we can have a drink there; I said ok. Seemed like a good plan.

We headed outside the rain was coming down as only Glasgow rain can. Malcolm put up his umbrella, it was one of those large golf type umbrellas; we both squeezed under it, even so we were going to get very wet heading for the station; which we did. We arrived at the Central station and had to run to platform 14 for the next train; just made it. Although the umbrella kept the rain off the top of us, our legs and trousers were soaking wet. We continued chatting on the train.

Even when we arrived at Ayr our trousers were still uncomfortably wet, but at least it had stopped raining. Malcolm suggested as we walked pass his apartment block, which was on the way back to my room; about another five minutes' walk. That I come in to dry off and have a coffee or another whiskey or both; given my domestic arrangements that seemed like an excellent idea.

His apartment was luxurious; as we were both dripping water on his hallway carpet, we took off our shoes and socks; but water was still dripping from our trousers'. He said better get them off too; I will get you something to put on. He headed into his bedroom and came out with two short, wrap type, dressing gowns; which we were to put on. We hung our trousers over a hot drying rail in a cupboard, along with our socks and our shoes; our jackets too. The back of my shirt was wet too, as was Malcolm's; so we hung them up to dry also.

We were both standing their naked and bare footed, apart from our underwear, which was thankfully dry. We put on the wrap gowns, closed and tied them off. We then went into the living area; Malcolm lit the gas fire which we stood in front of warming up, didn't realise how cold we were until we stood in front of the fire. Malcolm said; I will make us a coffee.

All we had on was the dressing gowns with our underwear shining through their fine silky material. Must admit I felt a wee bit exposed, but Malcolm seemed quite relaxed about having someone he has only known a few hours undressed like this in his apartment.

As Malcolm brought in the coffee, I sat down at one end of a large couch leaning on the arm; Malcolm sat at the other end. We enjoyed our warm coffee, as we warmed up internally; started chatting away again about all and nothing. Malcolm asked me quite politely, but bluntly, was I gay; I didn't know what to say and said no; why do you ask me that?

The 'Underground' we met in tonight is a gay venue; suddenly it occurred to me that the girls I was eavesdropping on had set me up. I shared this with Malcolm; he thought it was funny; it was.

He continued, have you ever thought you might be gay; I stumbled giving an answer; as I had, more than once. Before I could answer he said; it would make me happy if you were, or willing to explore if you are. I said I don't know; got flustered and blurted out; I have never had sex like that before. He replied; don't worry I can show you.

By now I was starting to get a bit sexually excited and aroused and could feel a bit of movement. Strangely enough that didn't bother me; it was quite exciting. Malcolm put his coffee cup down and mover over to me; we were now more or less touching. He leaned over and touched the back of my hand very gently. I twitched, and my arousal started to feel a bit of wetness start to form.

Malcolm leaned back against the couch and me; I could feel a strange sensation passing through our body contact and heat where we were touching. He then put his hand inside my leg and started to caress it. I twitched again and could feel more wetness forming. At this point he started to nibble my ear lobes, never had someone do that to me before, it was very sensual. I started to go very hard which was arousing me further.

His ear nibbling suddenly stung, as I turned to face him, he put his fingers across my lips, I smiled. I had never had that done to me before, not this way; I liked it too, my arousal was starting to hurt in the tightness of my underwear. He then undid the tie on my gown; then his. He started to rub the back of his hand on my underwear, my hardness grew in intensity and I could now feel myself wet.

Slowly he moved his hand inside my underwear and touched me skin to skin, I could feel myself starting to cum when he did this. I think I did. I could now feel his hands slowly sliding off my underwear; I really liked it. He removed his own underwear, and then slowly slid my gown of my shoulders; he slid his off also.

We were sitting their naked, touching and exchanging body heat, both having erections. He started to caress mine; I did the same to his. It wasn't long before I could feel cum building, and then start to move, as I twitched with each of his slow gentle strokes. My strokes on him became more erratic the more excited I became.

I couldn't control it anymore; I could feel an intense outburst rush start; I panicked; grabbed my discarded underwear off the arm of the couch to stem the outflow. It was intense; never felt anything like that before, it just kept coming as convulsions, before long it overwhelmed the underwear I was trying to hold it back with. My chest got swamped with it too. Malcolm was surprised by the intensity of it. He lifted his discarded underwear and helped me wipe up the mess.

We headed to his bathroom where I relieved myself of my cum, dropping the soiled underwear, now rags into the sink and ran water on them. Malcolm had a big walk in shower, which he had turned on, I stepped into it; I was never so relieved when the hot shower water hit me and washed away the remaining mess. Malcolm had also been hit with my overspray; the shared shower washed away both our messes.

We both laughed at what had just happened, Malcolm said you must have been storing that up for a while; never a truer word said. We then washed each other which also a very sensual thing to do; and have done to you.

We dried ourselves off and wrapped, our now wet towels, around us. Malcolm went into his bedroom and invited me to follow him in; I was a bit apprehensive in do this but I went anyway. He handed me a box of four new pairs of underwear; Christmas present, too small for me but should fit you.

There was a bright blue and red and black pair; what attracted my attention was a striped rainbow pair. I took them out of the box, Malcolm had left and gone into the living area, I tried them on, they were called tanga cut; never tried them before. Basically they were material at the front and back joined by an elastic waist band, where your thighs were fully exposed. I looked in the dressing mirror; I thought I looked quite sexy in them the way my thighs showed.

As I had no other clothes to hand I went into the living room with nothing else on. Malcolm was standing there with his wrap dressing gown on but open and untied with his underwear showing; he had on a similar patterned pair. He said I thought you might like them too, he handed me over my dressing gown, which I put on but left open too.

He suggested that I stay the night with him; I could sleep either on the couch or share his bed. He could see that I was unsure and said: we won't do anything else tonight and wait until tomorrow to see how, I feel about what has happened. I don't know why but I said 'ok' and he led the way to his bedroom.

We took off our gowns in unison and went into bed together, with only our rainbow underwear on. Malcolm switched the lights out, I could feel him and his warmth embrace me as he spooned with me; it was very nice and comforting; he said 'ok' I said 'yes'. Don't know how much time passed but we fell asleep embracing each other.

Next morning I awoke, alone, but could hear the television on in the living area and got up. I couldn't find my dressing gown; I really liked wearing it; went through into the living room naked and bare footed except for my rainbow underwear. Malcolm was sitting with his back to me at the dining table looking at his lap top; he had his gown on but untied.

I assumed he was watching some program on it, as I walked over I heard a strange voice say, 'hi Craig nice to see you', I quickly and nervously looked around the room; nobody. Then realised I had walked into the vision field of a skype call, with only my revealing almost not their rainbow underwear on.

Last time something like that happened to me was back home; when my sister was skyping on the fly, with my computer. Which sat on a desk that was blanked by my bedroom door as you walked in; and I walked into its vision field with only my, must admit skimpy, underwear on.

A handful of her class mates were watching at the other end, one took my photograph on her phone and then posted it on line. Before long my picture was all over the island; I never really lived it down as the girls kept ribbing me about when was I going to give them the full Monty show.

Malcolm introduced me to his skype friend's; Mike, a lawyer and Tim, a photographer; who were clearly a couple. As they were both sitting in a state of undress, like Malcolm and I were. Mike said; Malcolm told us all about you two last night; I wanted a hole to open up and swallow me. Malcolm said I did not; that was the prompt they both needed to investigate into what actually happened. Mike killed the inquisition by inviting us both round to his place for a Chinese meal that night. We were cornered, Malcolm looked at me; I nodded yes.

Tim said see you both tonight, at seven, and remember to bring your Toga gear. By the way Craig nice butt and legs; Mike agreed; see more of you later. I was very embarrassed and wondered what he meant by that. Tim also said; get Malcolm to show you the holiday photographs I took of us last summer; then hung up.

Malcolm explained that, at a blind (you bid for a sealed box) charity auction, he bought some Roman Toga's, donated by a theatre company. Sometimes when they had a private meal together they would dress up in them. I thought different; never done that before. I asked photographs? I will show you later. We both then retired to the kitchen and had breakfast.

Malcolm said you still want to see the photographs that Tim took on our last holiday; Yes. He opened a file on his lap top; there were about 20 photographs of the three of them, naked apart from hiking boots; they were all naturalists, belonging to a local club.

I also saw another file that showed a slightly more erotic top file picture and pointed to it. He opened it for me; its contents were very erotic and revealing; he said I will leave you to look at them. They were photographs of gay sex positions; I wasn't offended by them; but I was mesmerised by what they portrayed. They answered many of my unasked questions about gay sex; no commentary was needed.

As my wet clothes were now dry I went back to my B&B room to get some fresh clothes; I inadvertently left my gifted box of colourful underwear. As I had agreed to return to Malcolm's at four and we would both go together to Mike and Tim's; which was ten minutes' walk away. I could get them then.

I went round at four as agreed. Malcolm had dug out the Toga's that we were to wear, ironed them and laid them out on his bed to view; they looked good. Want to try yours on; Yes. It was a loose fit but was ok, looking in the mirror, you could see my rainbow underwear shine through; it was ok but. Malcolm suggested that I try it on with the black underwear; I did and it looked a lot better; bit sexier too.

As we could not walk around dressed in these Toga's, packed them away in a carrier bag with two bottles of wine. We headed round to Mike's and Tim's; when we arrived they were both dressed in their Toga's. We got dressed in their spare bedroom and joined them. Mike produced a bottle of wine that we started to consume, by the time the Chinese carry out arrived we had consumed over a bottle and a half of wine between us. Don't remember who went to the door when it arrived; might have been me.

We started our meal, drank another two bottles of wine between us; I think they forgot that Islanders have hollow legs and can consume alcohol with limited impairment. Tim was starting to show signs of inebriation. The discussions we had were very entheausticly portrayed and revealing; all having a sexual connotation. Then Tim said ok; tell us about you two last night, how you met, and what did you do; we saw the morning after film remember.

We told them not leaving out many details; they were engrossed. As provocateur Tim asked me bluntly; did you have proper sex together and was that my first time? I said No and Yes. The pot got stirred further by Mike when he said, but you will tonight; without thinking or hesitating I said yes; I hope so. Mike and Tim applauded; Malcolm laughed; I got an erection; which Tim sitting next to me lifted my Toga up, looked under it; and said yes he is ready.

The conversation gradually degenerated over the evening; as it does. We left about three in the morning; all of us inebriated. But not before Tim photographed us all in out Toga's and I had also to pose in only my black underwear showing off my exposed thigh, and as Malcolm and Mike were rubbing my thighs; it was very sensual.

We arrived back at Malcolm's, no question did you want to stay tonight. We both went into his bedroom together, undressed and went to bed. Alcohol had taken its toll on us; we both fell asleep with me embracing Malcolm this time.

The next morning we awoke when it was still dark, I started to get an erection but contained within my underwear; when I thought about what I had said last night. Malcolm touched it, I felt excited and reached down and slid off my underwear; I could feel Malcolm slide his off also. We turned and lay there facing each other, we could feel our erections touch; which added to the moment.

I lay back; Malcolm moved over me and then moved my legs up and apart then moved some pillows under me, raising me up ready to receive him. He said I will start to ease you; I didn't know what he meant at that time. He kneeled in front of me and applied some oil, and then I felt is finger then fingers entering me and move about. At first it was a bit painful then it eased and I started to enjoy it, really enjoy it as he massaged my prostrate I could start to feel cum forming and started to twitch in enjoyment.

He then said let's try and engage with each other; I felt more oil being applied, it was quite pleasant too. Then I could feel him now try to enter; I was still very tight at first then I felt it ease as I relaxed and he entered. I could feel him slowly travel inside me although I was still very tight and uncomfortable, but eased before long; I was enjoying this intrusion.

Malcolm started to withdraw and completely re-enter again, not so tight this time, his traveling in me was more exhilarating. Each time he withdrew and re-entered, now touching my prostrate gently, which was giving me a rush of adrenalin or something. I tried to hold back his withdrawal, as he asked me to do, his rhythm was slow and my excitement was building with each stroke.

I felt Malcolm's rhythm quicken and start to convulse he was starting to climax, by now I was being splattered with my pre-cum. I was also starting to convulse at an increasing rate, it was not convulsions like last night on the couch but equally exhilarating.

Malcolm's rhythm broke and he convulsed three or more times then stopped. I could feel his cum flow and press inside me, it was a fantastic feeling then it eased away as Malcolm withdrew.

We parted and lay there side by side, exhausted and were wet with sweat. We lay there for what seemed a long time before we recovered. Malcolm said your turn; my first time.

We changed position and I adjusted the pillows under Malcolm, I tried to engage but was struggling. Malcolm gave me a helping hand and I started to try and enter, it was difficult to do; then I managed it. First time I only travelled about half way in before I withdrew but not out; the next time I pushed harder and travelled in fully; I felt it touching something firm. Malcolm winced; I had been a bit to forceful.